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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (9)transporters (2) Show 11 proteins XML

enzymes (9)transporters (2) Show 11 proteins

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-05-30 20:55:59 UTC

HMDB ID

HMDB0000929

Secondary Accession Numbers

HMDB00929

Metabolite Identification

Common Name

L-Tryptophan

Description

Tryptophan (Trp) or L-tryptophan is an alpha-amino acid. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Amino acids are organic compounds that contain amino (-NH2) and carboxyl (-COOH) functional groups, along with a side chain (R group) specific to each amino acid. L-tryptophan is one of 20 proteinogenic amino acids, i.e., the amino acids used in the biosynthesis of proteins. Tryptophan is found in all organisms ranging from bacteria to plants to animals. It is classified as a non-polar, uncharged (at physiological pH) aromatic amino acid. Tryptophan is an essential amino acid, meaning the body cannot synthesize it, and it must be obtained from the diet. The requirement for tryptophan and protein decreases with age. The minimum daily requirement for adults is 3 mg/kg/day or about 200 mg a day. There is 400 mg of tryptophan in a cup of wheat germ. A cup of low-fat cottage cheese contains 300 mg of tryptophan and chicken and turkey contain up to 600 mg of tryptophan per pound (http://www.dcnutrition.com). Tryptophan is particularly plentiful in chocolate, oats, dried dates, milk, yogurt, cottage cheese, red meat, eggs, fish, poultry, sesame, chickpeas, almonds, sunflower seeds, pumpkin seeds, buckwheat, spirulina, and peanuts. Tryptophan is the precursor of both serotonin and melatonin. Melatonin is a hormone that is produced by the pineal gland in animals, which regulates sleep and wakefulness. Serotonin is a brain neurotransmitter, platelet clotting factor, and neurohormone found in organs throughout the body. Metabolism of tryptophan into serotonin requires nutrients such as vitamin B6, niacin, and glutathione. Niacin (also known as vitamin B3) is an important metabolite of tryptophan. It is synthesized via kynurenine and quinolinic acids, which are products of tryptophan degradation. There are a number of conditions or diseases that are characterized by tryptophan deficiencies. For instance, fructose malabsorption causes improper absorption of tryptophan in the intestine, which reduces levels of tryptophan in the blood and leads to depression. High corn diets or other tryptophan-deficient diets can cause pellagra, which is a niacin-tryptophan deficiency disease with symptoms of dermatitis, diarrhea, and dementia. Hartnup's disease is a disorder in which tryptophan and other amino acids are not absorbed properly. Symptoms of Hartnup's disease include skin rashes, difficulty coordinating movements (cerebellar ataxia), and psychiatric symptoms such as depression or psychosis. Tryptophan supplements may be useful for treating Hartnup's disease. Assessment of tryptophan deficiency is done through studying excretion of tryptophan metabolites in the urine or blood. Blood may be the most sensitive test because the amino acid tryptophan is transported in a unique way. Increased urination of tryptophan breakdown products (such as kynurenine) correlates with increased tryptophan degradation, which occurs with oral contraception, depression, mental retardation, hypertension, and anxiety states. Tryptophan plays a role in "feast-induced" drowsiness. Ingestion of a meal rich in carbohydrates triggers the release of insulin. Insulin, in turn, stimulates the uptake of large neutral branched-chain amino acids (BCAAs) into muscle, increasing the ratio of tryptophan to BCAA in the bloodstream. The increased tryptophan ratio reduces competition at the large neutral amino acid transporter (which transports both BCAAs and tryptophan), resulting in greater uptake of tryptophan across the blood-brain barrier into the cerebrospinal fluid (CSF). Once in the CSF, tryptophan is converted into serotonin and the resulting serotonin is further metabolized into melatonin by the pineal gland, which promotes sleep. Because tryptophan is converted into 5-hydroxytryptophan (5-HTP) which is then converted into the neurotransmitter serotonin, it has been proposed that consumption of tryptophan or 5-HTP may improve depression symptoms by increasing the level of serotonin in the brain. Tryptophan is sold over the counter in the United States (after being banned to varying extents between 1989 and 2005) and the United Kingdom as a dietary supplement for use as an antidepressant, anxiolytic, and sleep aid. It is also marketed as a prescription drug in some European countries for the treatment of major depression. There is evidence that blood tryptophan levels are unlikely to be altered by changing the diet, but consuming purified tryptophan increases the serotonin level in the brain, whereas eating foods containing tryptophan does not. This is because the transport system that brings tryptophan across the blood-brain barrier also transports other amino acids which are contained in protein food sources. Under certain situations, tryptophan can be a neurotoxin and a metabotoxin. A neurotoxin is a compound that causes damage to the brain and nerve tissues. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of tryptophan can be found in glutaric aciduria type I (glutaric acidemia type I or GA1). GA1 is an inherited disorder in which the body is unable to completely break down the amino acids lysine, hydroxylysine, and tryptophan due to a deficiency of mitochondrial glutaryl-CoA dehydrogenase (EC 1.3.99.7, GCDH). Excessive levels of their intermediate breakdown products (e.g. glutaric acid, glutaryl-CoA, 3-hydroxyglutaric acid, glutaconic acid) can accumulate and cause damage to the brain (and also other organs), but particularly the basal ganglia. Babies with glutaric acidemia type I are often born with unusually large heads (macrocephaly). Other symptoms include spasticity (increased muscle tone/stiffness) and dystonia (involuntary muscle contractions resulting in abnormal movement or posture), but many affected individuals are asymptomatic. High levels of tryptophan have also been implicated in eosinophilia-myalgia syndrome (EMS), an incurable and sometimes fatal flu-like neurological condition linked to the ingestion of large amounts of L-tryptophan. The risk of developing EMS increases with larger doses of tryptophan and increasing age. Some research suggests that certain genetic polymorphisms may be related to the development of EMS. The presence of eosinophilia is a core feature of EMS, along with unusually severe myalgia (muscle pain). It is thought that both tryptophan and certain unidentified tryptophan contaminants may contribute to EMS (PMID: 1763543 ). It has also been suggested that excessive tryptophan or elevation of its metabolites could play a role in amplifying some of the pathological features of EMS (PMID: 10721094 ). This pathological damage is further augmented by metabolites of the kynurenine pathway (a tryptophan degradation pathway). Reduced levels of tryptophan in the blood are typically seen when individuals are fighting chronic infections, suffering from traumatic injuries (burns or wounds) or experiencing sepsis (PMID: 26309411 ). Tryptophan is mainly catabolized through the enzymatic activity of two enzymes: indoleamine-2,3-dioxygenase (IDO) 1 and IDO2, both of which are expressed widely in human tissues, and both of which are induced by interferon gamma (IFN-gamma or IFNG). IDO1 and IDO2 generate tryptophan catabolites such as kynurenine and kynurenic acid. These tryptophan catabolites activate the aryl hydrocarbon receptor (AhR), which plays a key role immune regulation. The role of IDO1 and IDO2 is to effectively deplete tryptophan levels to starve infectious organisms (bacteria and parasites), thereby killing them or slowing their growth. On the other hand, the AhR activation leads to a state of immunosuppression and is intended to serve as a brake on the immune (overexpression of IFNG and IL-1B) response to the infectious organisms. Unfortunately, tryptophan starvation is often not effective against viruses or even all infectious microbes. As a result, this AhR activation by tryptophan catabolites can lead to a situation where viruses (or certain pathogens) continue to survive and multiply even while the immune system is effectively turning off. As a result, high levels of kynurenine and low levels of tryptophan (a high kynurenine to tryptophan ratio) can lead to or even be symptomatic of chronic viral or pathogenic infections or, at worse, sepsis and septic shock (PMID: 33338598 ; PMID: 21731667 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

  Mrv1652309042000142D          

 15 16  0  0  1  0            999 V2000
    0.0032   -0.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0830   -1.0830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8900   -1.2545    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3025   -0.5401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7504    0.0730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0054    0.8576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1095   -0.3685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3644    0.4161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8124    1.0291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1466    0.9750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1466    0.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8611   -0.2625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4321   -0.2625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4321   -1.0875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7177    0.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  5  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  7  1  0  0  0  0
  5  6  1  0  0  0  0
  6  9  2  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
 11 10  2  0  0  0  0
 12 11  1  0  0  0  0
 13 11  1  0  0  0  0
 13 14  1  1  0  0  0
 15 13  1  0  0  0  0
  1 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000929

> <DATABASE_NAME>
hmdb

> <SMILES>
N[C@@H](CC1=CNC2=C1C=CC=C2)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H12N2O2/c12-9(11(14)15)5-7-6-13-10-4-2-1-3-8(7)10/h1-4,6,9,13H,5,12H2,(H,14,15)/t9-/m0/s1

> <INCHI_KEY>
QIVBCDIJIAJPQS-VIFPVBQESA-N

> <FORMULA>
C11H12N2O2

> <MOLECULAR_WEIGHT>
204.2252

> <EXACT_MASS>
204.089877638

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
21.047414013171778

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-3-(1H-indol-3-yl)propanoic acid

> <ALOGPS_LOGP>
-1.10

> <JCHEM_LOGP>
-1.0854569138833579

> <ALOGPS_LOGS>
-2.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.1565885064574

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.5439286383469866

> <JCHEM_PKA_STRONGEST_BASIC>
9.396082567807317

> <JCHEM_POLAR_SURFACE_AREA>
79.11

> <JCHEM_REFRACTIVITY>
56.20280000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.36e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
L-tryptophan

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0       0.006  -0.490   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.155  -2.022   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      -1.661  -2.342   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      -2.431  -1.008   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.401   0.136   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.877   1.601   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.938  -0.688   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.414   0.777   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.383   1.921   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.007   1.820   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.007   0.280   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.341  -0.490   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.673  -0.490   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       2.673  -2.030   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       1.340   0.280   0.000  0.00  0.00           C+0
CONECT    1    2    5   15                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    1    4    6                                                  
CONECT    6    5    9                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9                                                       
CONECT    9    6    8                                                       
CONECT   10   11                                                            
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    1                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

COMPND    HMDB0000929
HETATM    1  N1  UNL     1       2.923  -1.892   0.959  1.00  0.00           N  
HETATM    2  C1  UNL     1       2.034  -0.913   0.356  1.00  0.00           C  
HETATM    3  C2  UNL     1       0.836  -0.812   1.287  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.177   0.141   0.832  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.424   1.396   1.308  1.00  0.00           C  
HETATM    6  N2  UNL     1      -1.442   1.968   0.630  1.00  0.00           N  
HETATM    7  C5  UNL     1      -1.853   1.075  -0.288  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.857   1.161  -1.231  1.00  0.00           C  
HETATM    9  C7  UNL     1      -3.088   0.078  -2.082  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.333  -1.067  -1.991  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.342  -1.123  -1.044  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.086  -0.064  -0.183  1.00  0.00           C  
HETATM   13  C11 UNL     1       2.747   0.367   0.262  1.00  0.00           C  
HETATM   14  O1  UNL     1       3.918   0.458   0.664  1.00  0.00           O  
HETATM   15  O2  UNL     1       2.110   1.463  -0.275  1.00  0.00           O  
HETATM   16  H1  UNL     1       3.926  -1.608   0.900  1.00  0.00           H  
HETATM   17  H2  UNL     1       2.724  -2.038   1.978  1.00  0.00           H  
HETATM   18  H3  UNL     1       1.715  -1.262  -0.655  1.00  0.00           H  
HETATM   19  H4  UNL     1       1.245  -0.567   2.294  1.00  0.00           H  
HETATM   20  H5  UNL     1       0.413  -1.859   1.328  1.00  0.00           H  
HETATM   21  H6  UNL     1       0.110   1.869   2.106  1.00  0.00           H  
HETATM   22  H7  UNL     1      -1.865   2.909   0.751  1.00  0.00           H  
HETATM   23  H8  UNL     1      -3.464   2.063  -1.313  1.00  0.00           H  
HETATM   24  H9  UNL     1      -3.891   0.199  -2.804  1.00  0.00           H  
HETATM   25  H10 UNL     1      -2.552  -1.877  -2.675  1.00  0.00           H  
HETATM   26  H11 UNL     1      -0.758  -2.045  -0.994  1.00  0.00           H  
HETATM   27  H12 UNL     1       2.430   1.981  -1.084  1.00  0.00           H  
CONECT    1    2   16   17
CONECT    2    3   13   18
CONECT    3    4   19   20
CONECT    4    5    5   12
CONECT    5    6   21
CONECT    6    7   22
CONECT    7    8    8   12
CONECT    8    9   23
CONECT    9   10   10   24
CONECT   10   11   25
CONECT   11   12   12   26
CONECT   13   14   14   15
CONECT   15   27
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(2S)-2-Amino-3-(1H-indol-3-yl)propanoic acid	ChEBI
(S)-alpha-Amino-1H-indole-3-propanoic acid	ChEBI
(S)-alpha-Amino-beta-(3-indolyl)-propionic acid	ChEBI
(S)-Tryptophan	ChEBI
L-(-)-Tryptophan	ChEBI
L-beta-3-Indolylalanine	ChEBI
Trp	ChEBI
Tryptophan	ChEBI
W	ChEBI
(2S)-2-Amino-3-(1H-indol-3-yl)propanoate	Generator
(S)-a-Amino-1H-indole-3-propanoate	Generator
(S)-a-Amino-1H-indole-3-propanoic acid	Generator
(S)-alpha-Amino-1H-indole-3-propanoate	Generator
(S)-Α-amino-1H-indole-3-propanoate	Generator
(S)-Α-amino-1H-indole-3-propanoic acid	Generator
(S)-a-Amino-b-(3-indolyl)-propionate	Generator
(S)-a-Amino-b-(3-indolyl)-propionic acid	Generator
(S)-alpha-Amino-beta-(3-indolyl)-propionate	Generator
(S)-Α-amino-β-(3-indolyl)-propionate	Generator
(S)-Α-amino-β-(3-indolyl)-propionic acid	Generator
L-b-3-Indolylalanine	Generator
L-Β-3-indolylalanine	Generator
(-)-Tryptophan	HMDB
(L)-Tryptophan	HMDB
(S)-1H-Indole-3-alanine	HMDB
(S)-2-Amino-3-(3-indolyl)propionic acid	HMDB
(S)-a-Amino-b-indolepropionate	HMDB
(S)-a-Amino-b-indolepropionic acid	HMDB
(S)-a-Aminoindole-3-propionate	HMDB
(S)-a-Aminoindole-3-propionic acid	HMDB
(S)-alpha-Amino-beta-indolepropionate	HMDB
(S)-alpha-Amino-beta-indolepropionic acid	HMDB
(S)-alpha-Aminoindole-3-propionate	HMDB
(S)-alpha-Aminoindole-3-propionic acid	HMDB
1-beta-3-Indolylalanine	HMDB
1beta-3-Indolylalanine	HMDB
1H-Indole-3-alanine	HMDB
2-Amino-3-indolylpropanoate	HMDB
2-Amino-3-indolylpropanoic acid	HMDB
3-(1H-indol-3-yl)-L-Alanine	HMDB
3-indol-3-Ylalanine	HMDB
Alpha'-amino-3-indolepropionic acid	HMDB
alpha-Aminoindole-3-propionic acid	HMDB
Ardeytropin	HMDB
H-TRP-OH	HMDB
Indole-3-alanine	HMDB
Kalma	HMDB
L-alpha-Amino-3-indolepropionic acid	HMDB
L-alpha-Aminoindole-3-propionic acid	HMDB
L-Tryptofan	HMDB
L-Tryptophane	HMDB
Lopac-T-0254	HMDB
Lyphan	HMDB
Optimax	HMDB
Pacitron	HMDB
Sedanoct	HMDB
Triptofano	HMDB
Trofan	HMDB
Tryptacin	HMDB
Tryptan	HMDB
Tryptophane	HMDB
Tryptophanum	HMDB
Ardeydorm	HMDB
L Tryptophan	HMDB
L-Tryptophan-ratiopharm	HMDB
Merck brand OF tryptophan	HMDB
Niddapharm brand OF tryptophan	HMDB
ICN brand OF tryptophan	HMDB
Levotryptophan	HMDB
PMS Tryptophan	HMDB
PMS-Tryptophan	HMDB
Ratiopharm brand OF tryptophan	HMDB
Esparma brand OF tryptophan	HMDB
Ratio-tryptophan	HMDB
L Tryptophan ratiopharm	HMDB
Naturruhe	HMDB
Tryptophan metabolism alterations	HMDB
Ardeypharm brand OF tryptophan	HMDB
Kalma brand OF tryptophan	HMDB
Pharmascience brand OF tryptophan	HMDB
Upsher-smith brand OF tryptophan	HMDB
Ratio tryptophan	HMDB

Chemical Formula

C₁₁H₁₂N₂O₂

Average Molecular Weight

204.2252

Monoisotopic Molecular Weight

204.089877638

IUPAC Name

(2S)-2-amino-3-(1H-indol-3-yl)propanoic acid

Traditional Name

L-tryptophan

CAS Registry Number

73-22-3

SMILES

N[C@@H](CC1=CNC2=C1C=CC=C2)C(O)=O

InChI Identifier

InChI=1S/C11H12N2O2/c12-9(11(14)15)5-7-6-13-10-4-2-1-3-8(7)10/h1-4,6,9,13H,5,12H2,(H,14,15)/t9-/m0/s1

InChI Key

QIVBCDIJIAJPQS-VIFPVBQESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indolyl carboxylic acids and derivatives. Indolyl carboxylic acids and derivatives are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indolyl carboxylic acids and derivatives

Direct Parent

Indolyl carboxylic acids and derivatives

Alternative Parents

Substituents

Indolyl carboxylic acid derivative
Alpha-amino acid
Alpha-amino acid or derivatives
L-alpha-amino acid
3-alkylindole
Indole
Aralkylamine
Benzenoid
Substituted pyrrole
Heteroaromatic compound
Pyrrole
Amino acid or derivatives
Amino acid
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Azacycle
Amine
Primary aliphatic amine
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Organonitrogen compound
Organooxygen compound
Primary amine
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

proteinogenic amino acid (CHEBI:16828 )
L-alpha-amino acid (CHEBI:16828 )
tryptophan (CHEBI:16828 )
erythrose 4-phosphate/phosphoenolpyruvate family amino acid (CHEBI:16828 )
Common amino acids (C00078 )

Ontology

Physiological effect

Health effect

Endocrine system disorder

Thyroidal or parathyroidal disorder

Thyroid dysfunction (HMDB: HMDB0000929)

Digestive system disorder

Hepatobiliary disorder

Hepatic disorder

Liver damage (PMID: 31434538)

Nervous system disorder

Nerve damage (PMID: 31434538)
Hereditary spastic paraplegia (HMDB: HMDB0000929)

Central nervous system disorder

Epilepsy (HMDB: HMDB0000929)
Olivopontocerebral atrophy (HMDB: HMDB0000929)
Friedreich's ataxia (HMDB: HMDB0000929)

Psychiatric disorder

Schizophrenia (HMDB: HMDB0000929)

Observation

Intervention

Periodontal Probing Depth (HMDB: HMDB0000929)

Circulatory system disorder

Blood and lymphatic system disorder

Leukocytic disorder

Leukemia (HMDB: HMDB0000929)

Genetic disorder

Inborn errors of metabolism

Hartnup disease (HMDB: HMDB0000929)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 12297216)
Breast milk (PMID: 24027187)
Cerebrospinal Fluid (CSF) (PMID: 2472426)
Saliva (PMID: 15995595)
Breast milk (HMDB: HMDB0000929)
Cerebrospinal fluid (HMDB: HMDB0000929)

Cell

Fibroblast

Fibroblast (HMDB: HMDB0000929)

Organ

Prostate (HMDB: HMDB0000929)
Placenta (HMDB: HMDB0000929)

Excreta

Biofluid or Excreta

Urine (PMID: 2026685)
Feces (PMID: 18052033)
Sweat (PMID: 22194922)

Cellular substructure

Extracellular (HMDB: HMDB0000929)
Cytoplasm (HMDB: HMDB0000929)

Organelle

Mitochondrion (HMDB: HMDB0000929)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000929)

Source

Exogenous

Exogenous (HMDB: HMDB0000929)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Emu (FooDB: FOOD00360)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)

Lagomorph

Caprae

Domestic goat (FooDB: FOOD00529)

Bovine

Swine

Wild boar (FooDB: FOOD00307)
Domestic pig (FooDB: FOOD00536)

Venison

Elk (FooDB: FOOD00359)
Deer (FooDB: FOOD00524)

Equine

Horse (FooDB: FOOD00378)

Herb and spice mixture

Curry powder (FooDB: FOOD00678)

Herbs and Spices (FooDB: FOOD00866)

Vegetable

Cabbage

Onion-family vegetable

Allium (FooDB: FOOD00005)
Garden onion (FooDB: FOOD00006)
Leek (FooDB: FOOD00007)
Garden onion (var.) (FooDB: FOOD00226)
Shallot (FooDB: FOOD00243)
Wild leek (FooDB: FOOD00396)
Red onion (FooDB: FOOD00962)
Green onion (FooDB: FOOD00963)
Onion-family vegetables (FooDB: FOOD00855)

Root vegetable

Shoot vegetable

Leaf vegetable

Common beet (FooDB: FOOD00025)
Endive (FooDB: FOOD00048)
Rocket salad (ssp.) (FooDB: FOOD00077)
Swamp cabbage (FooDB: FOOD00091)
Lettuce (FooDB: FOOD00095)
Garden cress (FooDB: FOOD00099)
Spinach (FooDB: FOOD00178)
Swiss chard (FooDB: FOOD00237)
Chicory leaves (FooDB: FOOD00250)
Garland chrysanthemum (FooDB: FOOD00333)
Corn salad (FooDB: FOOD00340)
Jute (FooDB: FOOD00389)
Lambsquarters (FooDB: FOOD00394)
Malabar spinach (FooDB: FOOD00404)
New Zealand spinach (FooDB: FOOD00415)
Yautia (FooDB: FOOD00510)
Ostrich fern (FooDB: FOOD00556)
Romaine lettuce (FooDB: FOOD00888)
Iceberg lettuce (FooDB: FOOD00973)
Pea shoots (FooDB: FOOD00975)
Yau choy (FooDB: FOOD00976)
Water spinach (FooDB: FOOD00977)
Rocket salad (FooDB: FOOD00244)
Green vegetables (FooDB: FOOD00872)

Fruit vegetable

Pepper (FooDB: FOOD00040)
Olive (FooDB: FOOD00121)
Avocado (FooDB: FOOD00130)
Garden tomato (FooDB: FOOD00171)
Cherry tomato (FooDB: FOOD00172)
Garden tomato (var.) (FooDB: FOOD00173)
Eggplant (FooDB: FOOD00174)
Pepper (C. baccatum) (FooDB: FOOD00231)
Pepper (C. chinense) (FooDB: FOOD00232)
Pepper (Capsicum) (FooDB: FOOD00233)
Groundcherry (FooDB: FOOD00371)
Pepper (C. frutescens) (FooDB: FOOD00428)
Mexican groundcherry (FooDB: FOOD00491)
Pepper (C. pubescens) (FooDB: FOOD00849)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Orange bell pepper (FooDB: FOOD00879)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)
Jalapeno pepper (FooDB: FOOD00955)
Cubanelle pepper (FooDB: FOOD00971)

Tuber

Stalk vegetable

Other vegetable

Giant butterbur (FooDB: FOOD00314)
Carob (FooDB: FOOD00321)
Chinese water chestnut (FooDB: FOOD00332)
Horseradish tree (FooDB: FOOD00379)
Sacred lotus (FooDB: FOOD00402)
Nopal (FooDB: FOOD00416)
Okra (FooDB: FOOD00420)
Sesbania flower (FooDB: FOOD00469)
Agave (FooDB: FOOD00563)
Narrowleaf cattail (FooDB: FOOD00564)
Heart of palm (FooDB: FOOD00718)
Tree fern (FooDB: FOOD00797)

Mushroom

Castanospermum australe (FooDB: FOOD00893)
Gentiana lutea (FooDB: FOOD00894)
Juniperus communis (FooDB: FOOD00895)
Albizia gummifera (FooDB: FOOD00896)

Vegetable product

Other vegetable product (FooDB: FOOD00671)

Brassica

Brassicas (FooDB: FOOD00857)

Fruit

Tropical fruit

Citrus

Lime (FooDB: FOOD00053)
Lemon (FooDB: FOOD00054)
Pummelo (FooDB: FOOD00055)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Sweet orange (FooDB: FOOD00057)
Grapefruit/Pummelo hybrid (FooDB: FOOD00255)
Grapefruit (FooDB: FOOD00256)
Persian lime (FooDB: FOOD00543)
Sour orange (FooDB: FOOD00918)
Mikan (FooDB: FOOD00932)
Clementine (FooDB: FOOD00959)
Citrus (FooDB: FOOD00859)

Pome

Berry

Black crowberry (FooDB: FOOD00075)
Strawberry (FooDB: FOOD00083)
Black huckleberry (FooDB: FOOD00084)
Sea-buckthornberry (FooDB: FOOD00087)
Mulberry (FooDB: FOOD00116)
Black mulberry (FooDB: FOOD00117)
Black chokeberry (FooDB: FOOD00136)
Blackcurrant (FooDB: FOOD00155)
Redcurrant (FooDB: FOOD00156)
Gooseberry (FooDB: FOOD00157)
Cloudberry (FooDB: FOOD00161)
Red raspberry (FooDB: FOOD00162)
Black raspberry (FooDB: FOOD00163)
Black elderberry (FooDB: FOOD00166)
Rowanberry (FooDB: FOOD00176)
Vaccinium (Blueberry, Cranberry, Huckleberry) (FooDB: FOOD00188)
Lowbush blueberry (FooDB: FOOD00189)
Sparkleberry (FooDB: FOOD00190)
Highbush blueberry (FooDB: FOOD00191)
American cranberry (FooDB: FOOD00192)
Bilberry (FooDB: FOOD00193)
Lingonberry (FooDB: FOOD00194)
Muscadine grape (FooDB: FOOD00203)
Common grape (FooDB: FOOD00204)
Arctic blackberry (FooDB: FOOD00207)
Bayberry (FooDB: FOOD00209)
Elliott's blueberry (FooDB: FOOD00210)
Canada blueberry (FooDB: FOOD00211)
Bog bilberry (FooDB: FOOD00212)
Buffalo currant (FooDB: FOOD00213)
European cranberry (FooDB: FOOD00217)
Deerberry (FooDB: FOOD00218)
Cascade huckleberry (FooDB: FOOD00220)
Oval-leaf huckleberry (FooDB: FOOD00221)
Evergreen huckleberry (FooDB: FOOD00222)
Red huckleberry (FooDB: FOOD00223)
Summer grape (FooDB: FOOD00227)
Fox grape (FooDB: FOOD00228)
Half-highbush blueberry (FooDB: FOOD00248)
Jostaberry (FooDB: FOOD00257)
Sweet rowanberry (FooDB: FOOD00265)
Skunk currant (FooDB: FOOD00267)
Squashberry (FooDB: FOOD00344)
Elderberry (FooDB: FOOD00358)
Grape (FooDB: FOOD00369)
Alaska blueberry (FooDB: FOOD00380)
Loganberry (FooDB: FOOD00400)
Ohelo berry (FooDB: FOOD00419)
Salmonberry (FooDB: FOOD00456)
Strawberry guava (FooDB: FOOD00482)
Boysenberry (FooDB: FOOD00542)
Chinese bayberry (FooDB: FOOD00852)
Saskatoon berry (FooDB: FOOD00884)
Nanking cherry (FooDB: FOOD00885)
Rabbiteye blueberry (FooDB: FOOD00898)
Blackberry (FooDB: FOOD00906)
Partridge berry (FooDB: FOOD00931)
Green grape (FooDB: FOOD00964)
Red grape (FooDB: FOOD00965)
Black plum (FooDB: FOOD00966)
Black raisin (FooDB: FOOD00968)
Chinese plum (FooDB: FOOD00978)
Green plum (FooDB: FOOD00979)
Wampee (FooDB: FOOD00980)
Goji (FooDB: FOOD00982)
Monk fruit (FooDB: FOOD00983)
Hawthorn (FooDB: FOOD00985)
Lantern fruit (FooDB: FOOD00986)
Cape gooseberry (FooDB: FOOD00988)
Rubus (Blackberry, Raspberry) (FooDB: FOOD00160)

Other fruit

Fig (FooDB: FOOD00081)
Date (FooDB: FOOD00135)
Jujube (FooDB: FOOD00388)

Drupe

Prunus (Cherry, Plum) (FooDB: FOOD00143)
Apricot (FooDB: FOOD00144)
Sweet cherry (FooDB: FOOD00145)
Sour cherry (FooDB: FOOD00146)
European plum (FooDB: FOOD00147)
Peach (FooDB: FOOD00149)
Nectarine (FooDB: FOOD00229)
Peach (var.) (FooDB: FOOD00230)
Common chokecherry (FooDB: FOOD00562)

Fruit product

Other fruit product (FooDB: FOOD00765)
Fruit preserve (FooDB: FOOD00660)

Fruits (FooDB: FOOD00871)

Cereal and cereal product

Cereal product

Whole grain cereal products (HMDB: HMDB0000929)
Pasta (FooDB: FOOD00273)
Bulgur (FooDB: FOOD00741)
Semolina (FooDB: FOOD00745)
Flour (FooDB: FOOD00799)
Biscuit (FooDB: FOOD00274)
Breakfast cereal (FooDB: FOOD00270)
Corn grits (FooDB: FOOD00813)
Other cereal product (FooDB: FOOD00272)

Cereal

Dough

Sourdough (FooDB: FOOD00275)

Leavened bread

Flat bread

Other bread

Potato bread (FooDB: FOOD00811)
Other bread (FooDB: FOOD00269)

Sweet bread

Raisin bread (FooDB: FOOD00817)

Bread products

Other bread product (FooDB: FOOD00805)

Cereals and cereal products (FooDB: FOOD00858)

Nut

Nuts (HMDB: HMDB0000929)
Cashew nut (FooDB: FOOD00011)
Peanut (FooDB: FOOD00016)
Brazil nut (FooDB: FOOD00024)
Pecan nut (FooDB: FOOD00044)
Chestnut (FooDB: FOOD00045)
Common hazelnut (FooDB: FOOD00062)
Black walnut (FooDB: FOOD00093)
Common walnut (FooDB: FOOD00094)
Pine nut (FooDB: FOOD00138)
Pistachio (FooDB: FOOD00140)
Almond (FooDB: FOOD00148)
Macadamia nut (M. tetraphylla) (FooDB: FOOD00225)
Japanese walnut (FooDB: FOOD00240)
Acorn (FooDB: FOOD00282)
Beech nut (FooDB: FOOD00299)
Butternut (FooDB: FOOD00316)
Chinese chestnut (FooDB: FOOD00331)
Walnut (FooDB: FOOD00608)
European chestnut (FooDB: FOOD00363)
Hazelnut (FooDB: FOOD00376)
Hickory nut (FooDB: FOOD00377)
Japanese chestnut (FooDB: FOOD00385)
Pili nut (FooDB: FOOD00432)
Colorado pinyon (FooDB: FOOD00433)
Macadamia nut (FooDB: FOOD00525)
Mixed nuts (FooDB: FOOD00771)

Milk and milk product

Dairy products (HMDB: HMDB0000929)

Other milk product

Fermented milk

Fermented milk product

Unfermented milk

Milk (Other mammals) (FooDB: FOOD00690)
Milk (Human) (FooDB: FOOD00666)
Milk (Cow) (FooDB: FOOD00618)
Cow milk, pasteurized, vitamin A + D added, 0% fat (FooDB: FOOD00889)
Cow milk, pasteurized, vitamin A + D added, 1% fat (FooDB: FOOD00890)
Cow milk, pasteurized, vitamin A + D added, 2% fat (FooDB: FOOD00891)
Cow milk, pasteurized, vitamin D added, 3.25% fat (FooDB: FOOD00892)

Egg

Eggs (HMDB: HMDB0000929)
Egg yolk (FooDB: FOOD00919)

Soy

Soy (HMDB: HMDB0000929)
Soy bean (FooDB: FOOD00085)

Lentils (FooDB: FOOD00098)

Other pulse

Lupine (FooDB: FOOD00104)
White lupine (FooDB: FOOD00403)

Bean

Green lentil (FooDB: FOOD00970)
Pulses (FooDB: FOOD00867)

Gourd

Watermelon (FooDB: FOOD00052)
Muskmelon (FooDB: FOOD00064)
Cucumber (FooDB: FOOD00065)
Cucurbita (FooDB: FOOD00066)
Bitter gourd (FooDB: FOOD00115)
Winter squash (FooDB: FOOD00283)
Butternut squash (FooDB: FOOD00317)
Calabash (FooDB: FOOD00318)
Chayote (FooDB: FOOD00325)
Towel gourd (FooDB: FOOD00492)
Wax gourd (FooDB: FOOD00499)
Tinda (FooDB: FOOD00559)
Horned melon (FooDB: FOOD00761)
Sunburst squash (pattypan squash) (FooDB: FOOD00874)
Green zucchini (FooDB: FOOD00875)
Yellow zucchini (FooDB: FOOD00876)
Japanese pumpkin (FooDB: FOOD00886)
Acorn squash (FooDB: FOOD00972)
Cantaloupe melon (FooDB: FOOD00984)

Coffee and coffee product

Coffee

Tea

Herbal tea

Hibiscus tea (FooDB: FOOD00723)
Greenthread tea (FooDB: FOOD00820)

Dish

Other dish

Ground meat

Sausage (FooDB: FOOD00652)
Pate (FooDB: FOOD00655)
Meatloaf (FooDB: FOOD00737)
Cold cut (FooDB: FOOD00770)

Pasta dish

Potato dish

American cuisine

Succotash (FooDB: FOOD00794)
Hushpuppy (FooDB: FOOD00762)

Jewish cuisine

Gefilte fish (FooDB: FOOD00833)

Tex-mex cuisine

Chili (FooDB: FOOD00707)
Burrito (FooDB: FOOD00704)
Nachos (FooDB: FOOD00710)
Taco (FooDB: FOOD00708)

Levantine cuisine

Hummus (FooDB: FOOD00845)

Sandwich

Berber cuisine

Couscous (FooDB: FOOD00740)

Mexican cuisine

Asian cuisine

Egg roll (FooDB: FOOD00717)

Latin american cuisine

Tamale (FooDB: FOOD00795)
Empanada (FooDB: FOOD00830)
Pupusa (FooDB: FOOD00829)
Arepa (FooDB: FOOD00831)

Sugar (FooDB: FOOD00651)

Dressing

Salad dressing (FooDB: FOOD00645)

Condiment

Seasoning

Salt (FooDB: FOOD00647)
Vinegar (FooDB: FOOD00628)

Sauce

Sauce (FooDB: FOOD00646)

Beverage

Fermented beverage

Beer (FooDB: FOOD00268)

Distilled beverage

Vodka (FooDB: FOOD00622)
Spirit (FooDB: FOOD00276)
Gin (FooDB: FOOD00625)
Liquor (FooDB: FOOD00616)
Rum (FooDB: FOOD00629)
Whisky (FooDB: FOOD00623)

Other beverage

Water

Water (FooDB: FOOD00664)

Nutritional beverage

Nutritional drink (FooDB: FOOD00754)

Alcoholic beverage

Other alcoholic beverage (FooDB: FOOD00278)

Aquatic origin

Crustacean

Fish

Atlantic herring (FooDB: FOOD00292)
Atlantic pollock (FooDB: FOOD00295)
Atlantic wolffish (FooDB: FOOD00296)
Striped bass (FooDB: FOOD00298)
Northern bluefin tuna (FooDB: FOOD00305)
Bluefish (FooDB: FOOD00306)
Burbot (FooDB: FOOD00313)
American butterfish (FooDB: FOOD00315)
Common carp (FooDB: FOOD00322)
Channel catfish (FooDB: FOOD00324)
Cisco (FooDB: FOOD00334)
Pacific cod (FooDB: FOOD00337)
Atlantic cod (FooDB: FOOD00338)
Atlantic croaker (FooDB: FOOD00345)
Cusk (FooDB: FOOD00346)
Freshwater drum (FooDB: FOOD00352)
Freshwater eel (FooDB: FOOD00357)
European anchovy (FooDB: FOOD00362)
Turbot (FooDB: FOOD00364)
Florida pompano (FooDB: FOOD00366)
Greenland halibut/turbot (FooDB: FOOD00370)
Grouper (FooDB: FOOD00372)
Hippoglossus (Common halibut) (FooDB: FOOD00375)
Pacific jack mackerel (FooDB: FOOD00383)
King mackerel (FooDB: FOOD00392)
Common ling (FooDB: FOOD00397)
Lingcod (FooDB: FOOD00398)
Milkfish (FooDB: FOOD00408)
Monkfish (FooDB: FOOD00409)
Striped mullet (FooDB: FOOD00412)
Ocean pout (FooDB: FOOD00417)
Pacific herring (FooDB: FOOD00424)
Pacific rockfish (FooDB: FOOD00426)
Northern pike (FooDB: FOOD00431)
Rainbow smelt (FooDB: FOOD00443)
Rainbow trout (FooDB: FOOD00444)
Orange roughy (FooDB: FOOD00448)
Sablefish (FooDB: FOOD00449)
Pink salmon (FooDB: FOOD00450)
Chum salmon (FooDB: FOOD00451)
Coho salmon (FooDB: FOOD00452)
Sockeye salmon (FooDB: FOOD00453)
Chinook salmon (FooDB: FOOD00454)
Atlantic salmon (FooDB: FOOD00455)
Spanish mackerel (FooDB: FOOD00460)
Scup (FooDB: FOOD00463)
Sea trout (FooDB: FOOD00468)
American shad (FooDB: FOOD00470)
Shark (FooDB: FOOD00471)
Sheefish (FooDB: FOOD00472)
Sheepshead (FooDB: FOOD00474)
Skipjack tuna (FooDB: FOOD00476)
Snapper (FooDB: FOOD00477)
Greater sturgeon (FooDB: FOOD00483)
White sucker (FooDB: FOOD00484)
Pumpkinseed sunfish (FooDB: FOOD00486)
Swordfish (FooDB: FOOD00487)
Tilefish (FooDB: FOOD00490)
Whitefish (FooDB: FOOD00503)
Whiting (FooDB: FOOD00504)
Yellowfin tuna (FooDB: FOOD00511)
Yellowtail amberjack (FooDB: FOOD00512)
Pollock (FooDB: FOOD00513)
Gadus (Common cod) (FooDB: FOOD00515)
Atlantic halibut (FooDB: FOOD00516)
Pacific halibut (FooDB: FOOD00517)
Percoidei (Bass and others) (FooDB: FOOD00526)
Flatfish (FooDB: FOOD00535)
Spot croaker (FooDB: FOOD00557)
Anchovy (FooDB: FOOD00566)
Carp bream (FooDB: FOOD00568)
Sturgeon (FooDB: FOOD00570)
Anguilliformes (FooDB: FOOD00577)
Gadiformes (FooDB: FOOD00580)
Lemon sole (FooDB: FOOD00583)
Norway pout (FooDB: FOOD00590)
Pacific ocean perch (FooDB: FOOD00598)
True sole (FooDB: FOOD00604)
Catfish (FooDB: FOOD00605)
Cichlidae (Tilapia) (FooDB: FOOD00699)
Japanese sea bass (FooDB: FOOD00974)
Clupeinae (Herring, Sardine, Sprat) (FooDB: FOOD00520)
Garfish (FooDB: FOOD00579)
Haddock (FooDB: FOOD00374)
Scombridae (Bonito, Mackerel, Tuna) (FooDB: FOOD00586)
Perciformes (FooDB: FOOD00527)
Pleuronectidae (Dab, Halibut, Plaice) (FooDB: FOOD00596)
Salmonidae (Salmon, Trout) (FooDB: FOOD00493)
Thunnus (FooDB: FOOD00607)
Dolphin fish (FooDB: FOOD00351)
Atlantic mackerel (FooDB: FOOD00293)
Painted comber (FooDB: FOOD00294)
Walleye (FooDB: FOOD00496)
Alaska pollock (FooDB: FOOD00497)
Pacific sardine (FooDB: FOOD00461)
Albacore tuna (FooDB: FOOD00514)
Smelt (FooDB: FOOD00519)
Devilfish (FooDB: FOOD00349)

Mollusk

Blue mussel (FooDB: FOOD00304)
Common octopus (FooDB: FOOD00339)
Cuttlefish (FooDB: FOOD00347)
Eastern oyster (FooDB: FOOD00356)
Pacific oyster (FooDB: FOOD00425)
Scallop (FooDB: FOOD00462)
Whelk (FooDB: FOOD00500)
Squid (FooDB: FOOD00532)
Marine mussel (FooDB: FOOD00587)
True oyster (FooDB: FOOD00592)
Abalone (FooDB: FOOD00279)
Bivalvia (Clam, Mussel, Oyster) (FooDB: FOOD00531)
Conch (FooDB: FOOD00611)

Seaweed

Roe

Roe (FooDB: FOOD00698)

Bivalvia

Clam (FooDB: FOOD00952)

Fish product

Other fish product (FooDB: FOOD00665)

Cetacean

Beluga whale (FooDB: FOOD00300)

Pinniped

Bearded seal (FooDB: FOOD00466)
Steller sea lion (FooDB: FOOD00465)

Confectionery

Other confectionery

Honey (FooDB: FOOD00626)
Marzipan (FooDB: FOOD00644)
Toffee (FooDB: FOOD00635)
Icing (FooDB: FOOD00700)

Dessert

Pastry (FooDB: FOOD00641)
Gelatin dessert (FooDB: FOOD00725)
Cake (FooDB: FOOD00636)
Pie (FooDB: FOOD00782)
Pudding (FooDB: FOOD00734)

Frozen dessert

Candy

Milk dessert

Sweet custard (FooDB: FOOD00716)
Junket (FooDB: FOOD00726)

Fat and oil

Animal fat

Vegetable fat

Margarine-like spread (FooDB: FOOD00844)
Margarine (FooDB: FOOD00843)
Shortening (FooDB: FOOD00783)

Cocoa and cocoa product

Cocoa product

Cocoa

Cocoa bean (FooDB: FOOD00182)

Baby food

Baby food (FooDB: FOOD00668)

Unclassified food or beverage

Unclassified food or beverage (FooDB: FOOD00672)

Snack

Synthetic

Personal care products

Personal care products (HMDB: HMDB0000929)

Endogenous

Plant

Animal

Animal (HMDB: HMDB0000929)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Tryptophan Metabolism (HMDB: HMDB0000929)
Transcription/Translation (HMDB: HMDB0000929)
Alanine Metabolism (PathBank: SMP0002415)
TRNA Charging 2 (PathBank: SMP0121283)
Inner Membrane Transport (PathBank: SMP0121270)
Transcription/Translation (HMDB: HMDB0000929)
TRNA Charging (PathBank: SMP0121281)
Tryptophan Metabolism II (PathBank: SMP0001930)
NAD Metabolism (PathBank: SMP0002338)
Camalexin Biosynthesis (PathBank: SMP0121212)

Disease pathway

Hartnup Disorder (HMDB: HMDB0000929)

Protein pathway

Protein Synthesis: Tryptophan (PathBank: SMP0119414)

Signaling pathway

Trp Operon (PathBank: SMP0000981)

Role

Industrial application

Personal care product

Personal care product (HMDB: HMDB0000929)

Nutraceutical (HMDB: HMDB0000929)
Hypoglycemic agent (HMDB: HMDB0000929)

Food and nutrition

Nutritional supplement (HMDB: HMDB0000929)

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0000929)

Biomarker

Leukemia (MarkerDB: MDB00000284)
Alzheimer's Disease (MarkerDB: MDB00000284)
Eosinophilic esophagitis (MarkerDB: MDB00000284)

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

Solid material processing agent

Protective agent

Antioxidant (HMDB: HMDB0000929)
Antioxidant (HMDB: HMDB0000929)

Indirect biological role

Metabotoxin

Metabotoxin (HMDB: HMDB0000929)

Biological role

Micronutrient (HMDB: HMDB0000929)
Plant metabolite (HMDB: HMDB0000929)
Animal metabolite (HMDB: HMDB0000929)
Essential amino acid (HMDB: HMDB0000929)
Hormone antagonist (HMDB: HMDB0000929)
Waste product (PMID: 35448883)
Anti anxiety (HMDB: HMDB0000929)
Anti dementia (HMDB: HMDB0000929)
Anti depressant (HMDB: HMDB0000929)
Anti dyskinetic (HMDB: HMDB0000929)
Anti hypertensive (HMDB: HMDB0000929)
Anti insomniac (HMDB: HMDB0000929)
Anti manic (HMDB: HMDB0000929)
Anti menopausal (HMDB: HMDB0000929)
Anti migraine (HMDB: HMDB0000929)
Anti Parkinsonian (HMDB: HMDB0000929)
Anti phenylketonuric (HMDB: HMDB0000929)
Anti rheumatic (HMDB: HMDB0000929)
Anti scoliotic (HMDB: HMDB0000929)
Carcinogenic (HMDB: HMDB0000929)
Essential (HMDB: HMDB0000929)
Hypnotic (HMDB: HMDB0000929)
Hypotensive (HMDB: HMDB0000929)
Insulinotonic (HMDB: HMDB0000929)
Monoamine precursor (HMDB: HMDB0000929)
Prolactinogenic (HMDB: HMDB0000929)
Serotoninergic (HMDB: HMDB0000929)
Tumor promoter (HMDB: HMDB0000929)

Modulator

Inhibitor

Enzyme inhibitor

Insulinase inhibitor (HMDB: HMDB0000929)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	230 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	13.4 mg/mL at 25 °C	YALKOWSKY,SH & DANNENFELSER,RM (1992)
LogP	-1.06	HANSCH,C ET AL. (1995)

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Baker	158.581	30932474
[M-H]-	Astarita_neg	146.3	30932474
[M+H]+	Astarita_pos	145.0	30932474
[M+H]+	Baker	154.225	30932474
[M-H]-	Not Available	158.581	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001785
[M+H]+	Not Available	152.0	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001785

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.36 g/L	ALOGPS
logP	-1.1	ALOGPS
logP	-1.1	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	2.54	ChemAxon
pKa (Strongest Basic)	9.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	79.11 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	56.2 m³·mol⁻¹	ChemAxon
Polarizability	21.05 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	147.623	31661259
DarkChem	[M-H]-	146.232	31661259
AllCCS	[M+H]+	146.284	32859911
AllCCS	[M-H]-	146.66	32859911
DeepCCS	[M+H]+	143.148	30932474
DeepCCS	[M-H]-	140.752	30932474
DeepCCS	[M-2H]-	174.607	30932474
DeepCCS	[M+Na]+	149.286	30932474
AllCCS	[M+H]+	146.3	32859911
AllCCS	[M+H-H2O]+	142.2	32859911
AllCCS	[M+NH4]+	150.1	32859911
AllCCS	[M+Na]+	151.2	32859911
AllCCS	[M-H]-	146.7	32859911
AllCCS	[M+Na-2H]-	146.8	32859911
AllCCS	[M+HCOO]-	147.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
L-Tryptophan	N[C@@H](CC1=CNC2=C1C=CC=C2)C(O)=O	3444.1	Standard polar	33892256
L-Tryptophan	N[C@@H](CC1=CNC2=C1C=CC=C2)C(O)=O	1998.1	Standard non polar	33892256
L-Tryptophan	N[C@@H](CC1=CNC2=C1C=CC=C2)C(O)=O	2307.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
L-Tryptophan,1TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H](N)CC1=C[NH]C2=CC=CC=C12	2197.3	Semi standard non polar	33892256
L-Tryptophan,1TMS,isomer #2	C[Si](C)(C)N[C@@H](CC1=C[NH]C2=CC=CC=C12)C(=O)O	2255.2	Semi standard non polar	33892256
L-Tryptophan,1TMS,isomer #3	C[Si](C)(C)N1C=C(C[C@H](N)C(=O)O)C2=CC=CC=C21	2272.6	Semi standard non polar	33892256
L-Tryptophan,2TMS,isomer #1	C[Si](C)(C)N[C@@H](CC1=C[NH]C2=CC=CC=C12)C(=O)O[Si](C)(C)C	2210.1	Semi standard non polar	33892256
L-Tryptophan,2TMS,isomer #1	C[Si](C)(C)N[C@@H](CC1=C[NH]C2=CC=CC=C12)C(=O)O[Si](C)(C)C	2179.7	Standard non polar	33892256
L-Tryptophan,2TMS,isomer #1	C[Si](C)(C)N[C@@H](CC1=C[NH]C2=CC=CC=C12)C(=O)O[Si](C)(C)C	2633.2	Standard polar	33892256
L-Tryptophan,2TMS,isomer #2	C[Si](C)(C)OC(=O)[C@@H](N)CC1=CN([Si](C)(C)C)C2=CC=CC=C12	2225.1	Semi standard non polar	33892256
L-Tryptophan,2TMS,isomer #2	C[Si](C)(C)OC(=O)[C@@H](N)CC1=CN([Si](C)(C)C)C2=CC=CC=C12	2195.8	Standard non polar	33892256
L-Tryptophan,2TMS,isomer #2	C[Si](C)(C)OC(=O)[C@@H](N)CC1=CN([Si](C)(C)C)C2=CC=CC=C12	2721.9	Standard polar	33892256
L-Tryptophan,2TMS,isomer #3	C[Si](C)(C)N([C@@H](CC1=C[NH]C2=CC=CC=C12)C(=O)O)[Si](C)(C)C	2414.6	Semi standard non polar	33892256
L-Tryptophan,2TMS,isomer #3	C[Si](C)(C)N([C@@H](CC1=C[NH]C2=CC=CC=C12)C(=O)O)[Si](C)(C)C	2259.1	Standard non polar	33892256
L-Tryptophan,2TMS,isomer #3	C[Si](C)(C)N([C@@H](CC1=C[NH]C2=CC=CC=C12)C(=O)O)[Si](C)(C)C	2831.1	Standard polar	33892256
L-Tryptophan,2TMS,isomer #4	C[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)O	2278.7	Semi standard non polar	33892256
L-Tryptophan,2TMS,isomer #4	C[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)O	2218.2	Standard non polar	33892256
L-Tryptophan,2TMS,isomer #4	C[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)O	2736.2	Standard polar	33892256
L-Tryptophan,3TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CC1=C[NH]C2=CC=CC=C12)N([Si](C)(C)C)[Si](C)(C)C	2411.1	Semi standard non polar	33892256
L-Tryptophan,3TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CC1=C[NH]C2=CC=CC=C12)N([Si](C)(C)C)[Si](C)(C)C	2329.2	Standard non polar	33892256
L-Tryptophan,3TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CC1=C[NH]C2=CC=CC=C12)N([Si](C)(C)C)[Si](C)(C)C	2530.5	Standard polar	33892256
L-Tryptophan,3TMS,isomer #2	C[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)O[Si](C)(C)C	2249.5	Semi standard non polar	33892256
L-Tryptophan,3TMS,isomer #2	C[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)O[Si](C)(C)C	2250.8	Standard non polar	33892256
L-Tryptophan,3TMS,isomer #2	C[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)O[Si](C)(C)C	2472.1	Standard polar	33892256
L-Tryptophan,3TMS,isomer #3	C[Si](C)(C)N([C@@H](CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)O)[Si](C)(C)C	2443.5	Semi standard non polar	33892256
L-Tryptophan,3TMS,isomer #3	C[Si](C)(C)N([C@@H](CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)O)[Si](C)(C)C	2353.1	Standard non polar	33892256
L-Tryptophan,3TMS,isomer #3	C[Si](C)(C)N([C@@H](CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)O)[Si](C)(C)C	2606.2	Standard polar	33892256
L-Tryptophan,4TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CC1=CN([Si](C)(C)C)C2=CC=CC=C12)N([Si](C)(C)C)[Si](C)(C)C	2469.8	Semi standard non polar	33892256
L-Tryptophan,4TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CC1=CN([Si](C)(C)C)C2=CC=CC=C12)N([Si](C)(C)C)[Si](C)(C)C	2388.7	Standard non polar	33892256
L-Tryptophan,4TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CC1=CN([Si](C)(C)C)C2=CC=CC=C12)N([Si](C)(C)C)[Si](C)(C)C	2421.3	Standard polar	33892256
L-Tryptophan,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CC1=C[NH]C2=CC=CC=C12	2475.2	Semi standard non polar	33892256
L-Tryptophan,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@@H](CC1=C[NH]C2=CC=CC=C12)C(=O)O	2522.1	Semi standard non polar	33892256
L-Tryptophan,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C=C(C[C@H](N)C(=O)O)C2=CC=CC=C21	2534.0	Semi standard non polar	33892256
L-Tryptophan,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CC1=C[NH]C2=CC=CC=C12)C(=O)O[Si](C)(C)C(C)(C)C	2710.2	Semi standard non polar	33892256
L-Tryptophan,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CC1=C[NH]C2=CC=CC=C12)C(=O)O[Si](C)(C)C(C)(C)C	2627.5	Standard non polar	33892256
L-Tryptophan,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CC1=C[NH]C2=CC=CC=C12)C(=O)O[Si](C)(C)C(C)(C)C	2814.8	Standard polar	33892256
L-Tryptophan,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12	2688.6	Semi standard non polar	33892256
L-Tryptophan,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12	2620.7	Standard non polar	33892256
L-Tryptophan,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12	2859.2	Standard polar	33892256
L-Tryptophan,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N([C@@H](CC1=C[NH]C2=CC=CC=C12)C(=O)O)[Si](C)(C)C(C)(C)C	2907.0	Semi standard non polar	33892256
L-Tryptophan,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N([C@@H](CC1=C[NH]C2=CC=CC=C12)C(=O)O)[Si](C)(C)C(C)(C)C	2700.5	Standard non polar	33892256
L-Tryptophan,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N([C@@H](CC1=C[NH]C2=CC=CC=C12)C(=O)O)[Si](C)(C)C(C)(C)C	2902.6	Standard polar	33892256
L-Tryptophan,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)C(=O)O	2750.2	Semi standard non polar	33892256
L-Tryptophan,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)C(=O)O	2650.4	Standard non polar	33892256
L-Tryptophan,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)C(=O)O	2880.6	Standard polar	33892256
L-Tryptophan,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=C[NH]C2=CC=CC=C12)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3104.4	Semi standard non polar	33892256
L-Tryptophan,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=C[NH]C2=CC=CC=C12)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2971.5	Standard non polar	33892256
L-Tryptophan,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=C[NH]C2=CC=CC=C12)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2818.8	Standard polar	33892256
L-Tryptophan,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)C(=O)O[Si](C)(C)C(C)(C)C	2870.3	Semi standard non polar	33892256
L-Tryptophan,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)C(=O)O[Si](C)(C)C(C)(C)C	2877.8	Standard non polar	33892256
L-Tryptophan,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)C(=O)O[Si](C)(C)C(C)(C)C	2789.6	Standard polar	33892256
L-Tryptophan,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N([C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)C(=O)O)[Si](C)(C)C(C)(C)C	3094.8	Semi standard non polar	33892256
L-Tryptophan,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N([C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)C(=O)O)[Si](C)(C)C(C)(C)C	2954.5	Standard non polar	33892256
L-Tryptophan,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N([C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)C(=O)O)[Si](C)(C)C(C)(C)C	2853.8	Standard polar	33892256
L-Tryptophan,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3278.2	Semi standard non polar	33892256
L-Tryptophan,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3154.7	Standard non polar	33892256
L-Tryptophan,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2786.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - L-Tryptophan GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)	splash10-0udi-0190000000-feaec8547634dddcad8c	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - L-Tryptophan GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)	splash10-0udi-0390000000-45a6c4fd79081597d44a	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - L-Tryptophan GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0udi-0290000000-34f7274f31a4cb321a0b	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - L-Tryptophan GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)	splash10-0fk9-9270000000-9761607cbe821f87f172	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - L-Tryptophan GC-MS (1 TMS)	splash10-001i-0900000000-3faeed7ad32e1755c03c	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - L-Tryptophan GC-MS (3 TMS)	splash10-0udi-0290000000-9c57a732e337fade3cb6	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - L-Tryptophan EI-B (Non-derivatized)	splash10-001i-0900000000-d054a214c1717940989f	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - L-Tryptophan EI-B (Non-derivatized)	splash10-0udi-0290000000-9860799c854e5c9ac1c7	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - L-Tryptophan GC-EI-TOF (Non-derivatized)	splash10-0udi-0190000000-feaec8547634dddcad8c	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - L-Tryptophan GC-EI-TOF (Non-derivatized)	splash10-0udi-0390000000-45a6c4fd79081597d44a	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - L-Tryptophan GC-EI-TOF (Non-derivatized)	splash10-0udi-0290000000-34f7274f31a4cb321a0b	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - L-Tryptophan GC-EI-QQ (Non-derivatized)	splash10-0udi-3729000000-86129db57aaf1a245f93	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - L-Tryptophan GC-EI-TOF (Non-derivatized)	splash10-0fk9-9270000000-9761607cbe821f87f172	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - L-Tryptophan GC-MS (Non-derivatized)	splash10-001i-0900000000-3faeed7ad32e1755c03c	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - L-Tryptophan GC-MS (Non-derivatized)	splash10-0udi-0290000000-9c57a732e337fade3cb6	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Tryptophan GC-MS (Non-derivatized) - 70eV, Positive	splash10-0560-4900000000-fa932bc4cffed0ca66b7	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Tryptophan GC-MS (1 TMS) - 70eV, Positive	splash10-00e9-9560000000-6829a8b2a2096883999f	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Tryptophan GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Tryptophan GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Tryptophan GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Tryptophan GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Tryptophan GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Tryptophan GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Tryptophan LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOF	splash10-0udi-0290602010-c09c931538bff74ac400	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Tryptophan LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOF	splash10-0a4i-0900000000-0fed327c2a56f556e04c	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Tryptophan LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOF	splash10-0udi-0090000000-98ec1c2c012e58eab924	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Tryptophan LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOF	splash10-00di-0090000000-fc77784da5d9b288d751	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Tryptophan LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOF	splash10-0udi-0290601010-d6f94902c0cf639cb7bc	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Tryptophan LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOF	splash10-0a4i-0900000000-27633a4f7ecfac45c730	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Tryptophan LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOF	splash10-0udi-0090000000-ee6cb8392b2e8d644bc1	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Tryptophan LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOF	splash10-004i-0090000000-d81c86eceee1c9824b02	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Tryptophan LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOF	splash10-0udi-0190000000-0e8b883dc8ab06c89d77	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Tryptophan LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOF	splash10-0uxu-2940000000-cb35b9680612e19d8b3a	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Tryptophan LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOF	splash10-014i-2900000000-7cc592351cc616b1d75f	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Tryptophan LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOF	splash10-014i-1900000000-987615a0add5eb2c3169	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Tryptophan LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOF	splash10-014i-1900000000-f150d9d1e19c72d337a8	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Tryptophan LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOF	splash10-0uxr-2960000000-f4c878f3abb1609bb5c5	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Tryptophan LC-ESI-QTOF , negative-QTOF	splash10-0udi-0090000000-c73c9b49139319c80b18	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Tryptophan LC-ESI-QTOF , negative-QTOF	splash10-0gb9-0930000000-da94834297fcc5b3d3c5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Tryptophan LC-ESI-QTOF , negative-QTOF	splash10-014i-0900000000-94061fd1f6b08445cdf3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Tryptophan LC-ESI-QTOF , negative-QTOF	splash10-014i-0900000000-e78172f4f27df232466e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Tryptophan LC-ESI-QTOF , negative-QTOF	splash10-014i-0900000000-93406e2cdb79770abc7d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Tryptophan LC-ESI-QQ , negative-QTOF	splash10-0udi-0190000000-0e8b883dc8ab06c89d77	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Tryptophan LC-ESI-QQ , negative-QTOF	splash10-0uxu-2940000000-cb35b9680612e19d8b3a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Tryptophan LC-ESI-QQ , negative-QTOF	splash10-014i-2900000000-5187dac98dbd6834d6ba	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Tryptophan LC-ESI-QQ , negative-QTOF	splash10-014i-1900000000-987615a0add5eb2c3169	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Tryptophan LC-ESI-QQ , negative-QTOF	splash10-014i-1900000000-174bb4d4390c75ae9a09	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Tryptophan LC-ESI-ITFT , negative-QTOF	splash10-0a4i-0900000000-0fed327c2a56f556e04c	2017-09-14	HMDB team, MONA	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Experimental 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, experimental)	2021-10-10	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Blood
Breast Milk
Cerebrospinal Fluid (CSF)
Feces
Saliva
Sweat
Urine

Tissue Locations

Fibroblasts
Neuron
Placenta
Prostate

Pathways

Name	SMPDB/PathBank	KEGG
Tryptophan metabolism	Not Available
Transcription/Translation	SMP00019	Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	22007635	details
Blood	Detected and Quantified	54.5 +/- 9.7 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected and Quantified	78.4 +/- 15.5 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected and Quantified	18-55 uM	Newborn (0-30 days old)	Both	Normal	BC Children's Hos...	details
Blood	Detected and Quantified	25-80 uM	Infant (1 - 3 months old)	Both	Normal	BC Children's Hos...	details
Blood	Detected and Quantified	21-80 uM	Children (3 months - 6 years old)	Both	Normal	BC Children's Hos...	details
Blood	Detected and Quantified	25-70 uM	Children (6 - 18 years old)	Both	Normal	BC Children's Hos...	details
Blood	Detected and Quantified	44.0 (37.0-51.0) uM	Adult (>18 years old)	Both	Normal	12297216	details
Blood	Detected and Quantified	81.3 +/- 3.36 uM	Adult (>18 years old)	Both	Normal	25004141	details
Blood	Detected and Quantified	87.4 (75.6-98.6) uM	Newborn (0-30 days old)	Not Available	Normal	25754623	details
Blood	Detected and Quantified	48.7 +/- 11.6 uM	Adult (>18 years old)	Female	Normal	Geigy Scientific ...	details
Blood	Detected and Quantified	101.5 +/- 27.2 uM	Newborn (0-30 days old)	Both	Normal	Geigy Scientific ...	details
Blood	Detected and Quantified	45.0 +/- 9.0 uM	Adult (>18 years old)	Male	Normal	Geigy Scientific ...	details
Blood	Detected and Quantified	73.9 (63-87) uM	Infant (0-1 year old)	Not Available	Normal	25754623	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	19678709	details
Blood	Detected and Quantified	69.71 +/- 0.99 uM	Adult (>18 years old)	Both	Normal	19390223	details
Blood	Detected and Quantified	63.0 +/- 10.7 uM	Adult (>18 years old)	Both	Normal	28278231	details
Blood	Detected and Quantified	36.5(20.6-51.8) uM	Children (1-13 uears old)	Both	Normal	27294788	details
Blood	Detected and Quantified	40.0-95.0 uM	Adult (>18 years old)	Both	Normal	The Metabolo...	details
Breast Milk	Detected and Quantified	3.2 +/- 1.3 uM	Adult (>18 years old)	Female	Normal	24027187	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	5 +/- 3 uM	Adult (>18 years old)	Both	Normal	18502700	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	1.3 +/- 0.4 uM	Adult (>18 years old)	Both	Normal	Geigy Scientific ...	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.96 +/- 8.83 uM	Children (1 - 13 years old)	Female	Normal	Geigy Scientific ...	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	1.18 +/- 1.15 uM	Children (1 - 13 years old)	Male	Normal	Geigy Scientific ...	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	2.32 +/- 0.09 uM	Adult (>18 years old)	Not Specified	Normal	1422788	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	2.25 +/- 0.95 uM	Adult (>18 years old)	Not Specified	Normal	6182788	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	20.4 +/- 8.2 uM	Adult (>18 years old)	Both	Normal	15911239	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	2.0 +/- 0.53 uM	Adult (>18 years old)	Not Specified	Normal	11383938	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	2.0 (1.2-2.5) uM	Adult (>18 years old)	Not Specified	Normal	2580417	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	15.9 +/- 4.1 uM	Adult (>18 years old)	Not Specified	Normal	22546835	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	2.64 +/- 0.52 uM	Adult (>18 years old)	Both	Normal	7595563	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.5-8 uM	Children (0 - 10 years old)	Both	Normal	BC Children's Hos...	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.5-9 uM	Adolescent (>11 years old)	Both	Normal	BC Children's Hos...	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	2.3 uM	Children (1-13 years old)	Both	Normal	2472426	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified	Not Quantified	Children (1-13 years old)	Both	Normal	21970810	details
Feces	Detected but not Quantified	Not Quantified	Children (1-13 years old)	Both	Normal	24130822	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Both	Normal	27609529	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Normal	27609529	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	18052033	details
Feces	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	19573517	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	Normal	25985090	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	21761941	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Normal	26709303	details
Feces	Detected and Quantified	170 +/- 110 nmol/g wet feces	Adult (>18 years old)	Both	Normal	27624970	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified	Not Quantified	Children (1-13 years old)	Not Specified	Normal	27452636	details
Feces	Detected and Quantified	20 +/- 20 nmol/g wet feces	Adult (>18 years old)	Both	Normal	27624970	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Children (1-13 years old)	Not Specified	Normal	21970810	details
Saliva	Detected and Quantified	0.5 +/- 0.5 uM	Adult (>18 years old)	Both	Normal	15995595	details
Saliva	Detected and Quantified	0.46 +/- 0.31 uM	Adult (>18 years old)	Female	Normal	23857558	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	20300169	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected and Quantified	4.80 +/- 3.41 uM	Adult (>18 years old)	Both	Normal	Zerihun T. Dame, ...	details
Sweat	Detected and Quantified	< 10 uM	Adult (60 years old)	Male	Normal	22194922	details
Sweat	Detected and Quantified	< 10 uM	Adult (40 years old)	Male	Normal	22194922	details
Sweat	Detected but not Quantified	Not Quantified	Adult	Both	Normal	26755145	details
Urine	Detected and Quantified	2.04 - 21.03 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	BC Children's Hos...	details
Urine	Detected and Quantified	4.97 - 46.02 umol/mmol creatinine	Infant (1 - 6 months old)	Both	Normal	BC Children's Hos...	details
Urine	Detected and Quantified	4.97 - 46.02 umol/mmol creatinine	Infant (6 months - <1 year old)	Both	Normal	BC Children's Hos...	details
Urine	Detected and Quantified	4.97 - 46.02 umol/mmol creatinine	Children (1 - 2 years old)	Both	Normal	BC Children's Hos...	details
Urine	Detected and Quantified	2.04 - 27.02 umol/mmol creatinine	Children (2 - 4 years old)	Both	Normal	BC Children's Hos...	details
Urine	Detected and Quantified	2.04 - 27.02 umol/mmol creatinine	Children (4 - 13 years old)	Both	Normal	BC Children's Hos...	details
Urine	Detected and Quantified	2.04 - 27.02 umol/mmol creatinine	Adolescent (13 - 21 years old)	Both	Normal	BC Children's Hos...	details
Urine	Detected and Quantified	2.04 - 14.02 umol/mmol creatinine	Adult (>21 years old)	Both	Normal	BC Children's Hos...	details
Urine	Detected and Quantified	1.13-34.27 umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	Mayo Clinic	details
Urine	Detected and Quantified	20.35 +/- 22.61 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	19468821	details
Urine	Detected and Quantified	23.74 +/- 31.66 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	19468821	details
Urine	Detected and Quantified	26.00 +/- 32.79 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	19468821	details
Urine	Detected and Quantified	7.8 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	19309105	details
Urine	Detected and Quantified	1.70-25.90 umol/mmol creatinine	Adolescent (13-18 years old)	Not Specified	Normal	Mayo Clinic	details
Urine	Detected and Quantified	7.377 (3.917-12.274) umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	14055140	details
Urine	Detected and Quantified	2.45-29.40 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	David F. Putnam C...	details
Urine	Detected and Quantified	13.52 +/- 7.37 umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	2026685	details
Urine	Detected and Quantified	1.86-6.03 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	32340350	details
Urine	Detected and Quantified	3.22 +/- 0.97 umol/mmol creatinine	Newborn (0-30 days old)	Female	Normal	32340350	details
Urine	Detected and Quantified	3.44 +/- 0.99 umol/mmol creatinine	Newborn (0-30 days old)	Male	Normal	32340350	details
Urine	Detected and Quantified	3.6-6.2 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	27012787	details
Urine	Detected and Quantified	2.036-12.90 umol/mmol creatinine	Adult (>18 years old)	Not Specified	Normal	Mayo Clinic	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected and Quantified	4.62 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Shaykhutdinov RA,...	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	1.58-35.63 umol/mmol creatinine	Infant (0-1 year old)	Not Specified	Normal	Mayo Clinic	details
Urine	Detected and Quantified	11.931 +/- 6.642 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Analysis of 30 no...	details
Urine	Detected and Quantified	1.21-72.48 umol/mmol creatinine	Newborn (0-30 days old)	Female	Normal	25536744	details
Urine	Detected and Quantified	0.45-15.92 umol/mmol creatinine	Newborn (0-30 days old)	Male	Normal	25536744	details
Urine	Detected and Quantified	11.48 +/- 16.66 umol/mmol creatinine	Newborn (0-30 days old)	Female	Normal	25536744	details
Urine	Detected and Quantified	4.0 +/- 3.9 umol/mmol creatinine	Newborn (0-30 days old)	Male	Normal	25536744	details
Urine	Detected and Quantified	9.57 +/- 7.27 umol/mmol creatinine	Children (0-2 years old)	Male	Normal	25536744	details
Urine	Detected and Quantified	9.85 +/- 6.69 umol/mmol creatinine	Children (0-2 years old)	Female	Normal	25536744	details
Urine	Detected and Quantified	5.6 (2.1-9.3) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	1.58-35.63 umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	Mayo Clinic	details
Urine	Detected and Quantified	3.82 (2.59-6.49) umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	Analysis of 40 NI...	details
Urine	Detected and Quantified	6.3 (3.4-11.1) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	10-40 umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	30830347	details
Urine	Detected and Quantified	4.4-6.9 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	27012787	details
Urine	Detected and Quantified	3.9 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	21388201	details
Urine	Detected and Quantified	5.263 (1.316-9.211) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Not Available	details
Urine	Detected and Quantified	1.13-34.27 umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	Mayo Clinic	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Schizophrenia	22007635	details
Blood	Detected and Quantified	63.6 uM	Infant (0-1 year old)	Female	Nicotinamide Adenine Dinucleotide Deficiency	28792876	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Ovarian cancer	22309680	details
Blood	Detected and Quantified	83.3 +/- 26.0 uM	Adult (>18 years old)	Male	Schizophrenia	2480613	details
Blood	Detected and Quantified	80.2 +/- 22.0 uM	Adult (>18 years old)	Female	Schizophrenia	2480613	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Oesophageal cancer	22291914	details
Blood	Detected and Quantified	76.2 +/- 15.4 uM	Children (1-13 years old)	Both	Obesity	Metabolomics reve...	details
Blood	Detected and Quantified	84.6 +/- 16.7 uM	Children (1-13 years old)	Both	Obesity	Metabolomics reve...	details
Blood	Detected and Quantified	31.6 (29.6-33.6) uM	Adult (>18 years old)	Both	Epilepsy	14992292	details
Blood	Detected and Quantified	37.2 (34.3-40.1) uM	Adult (>18 years old)	Both	Epilepsy	14992292	details
Blood	Detected and Quantified	53.3 (50.3-56.3) uM	Adult (>18 years old)	Both	Epilepsy	14992292	details
Blood	Detected and Quantified	27.2(8.3-35) uM	Adult (>18 years old)	Both	Sepsis	26847922	details
Blood	Detected and Quantified	101 +/- 4.48 uM	Adult (>18 years old)	Both	Schizophrenia	25004141	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25105552	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	19678709	details
Blood	Detected and Quantified	63.51 +/- 2.04 uM	Adult (>18 years old)	Both	Schizophrenia	19390223	details
Blood	Detected and Quantified	33.06 +/- 8.99 uM	Adult (>18 years old)	Both	Alzheimer's disease	17031479	details
Blood	Detected and Quantified	36.7(25.2-50.8) uM	Children (1-13 uears old)	Both	Environmental enteric dysfunction	27294788	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	2.035 +/- 0.649 uM	Adult (>18 years old)	Not Specified	celiac disease	6182788	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0018 +/- 0.0003 uM	Adult (>18 years old)	Both	Hypothyroidism	9849813	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	1.6 +/- 0.3 uM	Adult (>18 years old)	Both	Hypothyroidism	9849813	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	1.0 +/- 0.2 uM	Children (1-13 years old)	Both	Hartnup Disease	2472426	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	1.7 +/- 0.27 uM	Adult (>18 years old)	Both	Epilepsy	1705463	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	1.6+/- 0.57 uM	Adult (>18 years old)	Both	Epilepsy	1705463	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	1.7 +/- 0.4 uM	Adult (>18 years old)	Not Specified	Epilepsy	1705463	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	1.68 +/- 0.52 uM	Adult (>18 years old)	Both	Epilepsy	1705463	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	14.3 +/- 12.5 uM	Adult (>18 years old)	Not Specified	Epilepsy	1705463	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	11.5 +/- 8.2 uM	Adult (>18 years old)	Not Specified	Epilepsy	1705463	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	13.0 +/- 5.2 uM	Children (1-13 years old)	Not Specified	Leukemia	15911239	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	12.8 +/- 3.5 uM	Children (1-13 years old)	Not Specified	Leukemia	15911239	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	2.42 +/- 0.14 uM	Adult (>18 years old)	Not Specified	Olivopontocerebellar atrophy (OPCA)	11383938	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	1.80 +/- 0.2 uM	Adult (>18 years old)	Not Specified	Autosomal recessive spastic ataxia of Charlevoix-Saguena	11383938	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	1.8 +/- 0.3 uM	Adult (>18 years old)	Not Specified	Hypothyroidism	9849813	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	1.3 +/- 0.32 uM	Adult (>18 years old)	Both	Alzheimer's disease	17031479	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	2.4 +/- 0.13 uM	Not Specified	Not Specified	Friedreich's ataxia	11383938	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	2.67 +/- 0.6 uM	Adult (>18 years old)	Both	Schizophrenia	7595563	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	CCD	19636438	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	27015276	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Ileal Crohn's disease	19636438	details
Feces	Detected but not Quantified	Not Quantified	Children (1-13 years old)	Both	celiac disease	21970810	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	ankylosing spondylitis	Tie-juan Sha...	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	rheumatoid arthritis	Tie-juan Sha...	details
Feces	Detected but not Quantified	Not Quantified	Children (1-13 years old)	Both	Autism	24130822	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Both	Crohns disease	27609529	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Both	Ulcerative colitis	27609529	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Crohns disease	27609529	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Ulcerative colitis	27609529	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Irritable bowel syndrome	21761941	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Ulcerative colitis	21761941	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Feces	Detected but not Quantified	Not Quantified	Children (1-13 years old)	Not Specified	celiac disease	27452636	details
Feces	Detected but not Quantified	Not Quantified	Children (1-13 years old)	Not Specified	Treated celiac disease	21970810	details
Saliva	Detected and Quantified	0.22 +/- 0.16 uM	Adult (>18 years old)	Male	Alzheimer's disease	23857558	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Oral cancer	20300169	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Breast cancer	20300169	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	Pancreatic cancer	20300169	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	Periodontal diseases	20300169	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Attachment loss	31026179	details
Saliva	Detected and Quantified	0.40 +/- 0.21 uM	Adult (>18 years old)	Male	Frontotemporal lobe dementia	23857558	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Periodontal Probing Depth	31026179	details
Saliva	Detected and Quantified	0.60 +/- 0.49 uM	Adult (>18 years old)	Both	Lewy body disease	23857558	details
Urine	Detected and Quantified	10.707-21.382 umol/mmol creatinine	Children (1-13 years old)	Female	Tryptophanuria with dwarfism	14055140	details
Urine	Detected and Quantified	7.83 +/- 7.48 umol/mmol creatinine	Adult (>18 years old)	Both	Cachexia	18953024	details
Urine	Detected and Quantified	12.011 +/- 6.328 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	details
Urine	Detected and Quantified	1.19 +/- 0.23 umol/mmol creatinine	Adult (>18 years old)	Both	Alzheimer's disease	17031479	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25105552	details

Associated Disorders and Diseases

Disease References

Epilepsy
Rainesalo S, Keranen T, Palmio J, Peltola J, Oja SS, Saransaari P: Plasma and cerebrospinal fluid amino acids in epileptic patients. Neurochem Res. 2004 Jan;29(1):319-24. [PubMed:14992292 ] Botez MI, Young SN: Effects of anticonvulsant treatment and low levels of folate and thiamine on amine metabolites in cerebrospinal fluid. Brain. 1991 Feb;114 ( Pt 1A):333-48. [PubMed:1705463 ]
Schizophrenia
Alfredsson G, Wiesel FA: Monoamine metabolites and amino acids in serum from schizophrenic patients before and during sulpiride treatment. Psychopharmacology (Berl). 1989;99(3):322-7. [PubMed:2480613 ] Do KQ, Lauer CJ, Schreiber W, Zollinger M, Gutteck-Amsler U, Cuenod M, Holsboer F: gamma-Glutamylglutamine and taurine concentrations are decreased in the cerebrospinal fluid of drug-naive patients with schizophrenic disorders. J Neurochem. 1995 Dec;65(6):2652-62. [PubMed:7595563 ] Fukushima T, Iizuka H, Yokota A, Suzuki T, Ohno C, Kono Y, Nishikiori M, Seki A, Ichiba H, Watanabe Y, Hongo S, Utsunomiya M, Nakatani M, Sadamoto K, Yoshio T: Quantitative analyses of schizophrenia-associated metabolites in serum: serum D-lactate levels are negatively correlated with gamma-glutamylcysteine in medicated schizophrenia patients. PLoS One. 2014 Jul 8;9(7):e101652. doi: 10.1371/journal.pone.0101652. eCollection 2014. [PubMed:25004141 ] Kim YK, Myint AM, Verkerk R, Scharpe S, Steinbusch H, Leonard B: Cytokine changes and tryptophan metabolites in medication-naive and medication-free schizophrenic patients. Neuropsychobiology. 2009;59(2):123-9. doi: 10.1159/000213565. Epub 2009 Apr 22. [PubMed:19390223 ] Xuan J, Pan G, Qiu Y, Yang L, Su M, Liu Y, Chen J, Feng G, Fang Y, Jia W, Xing Q, He L: Metabolomic profiling to identify potential serum biomarkers for schizophrenia and risperidone action. J Proteome Res. 2011 Dec 2;10(12):5433-43. doi: 10.1021/pr2006796. Epub 2011 Nov 8. [PubMed:22007635 ]
Alzheimer's disease
Fonteh AN, Harrington RJ, Tsai A, Liao P, Harrington MG: Free amino acid and dipeptide changes in the body fluids from Alzheimer's disease subjects. Amino Acids. 2007 Feb;32(2):213-24. Epub 2006 Oct 10. [PubMed:17031479 ] Tsuruoka M, Hara J, Hirayama A, Sugimoto M, Soga T, Shankle WR, Tomita M: Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis. 2013 Oct;34(19):2865-72. doi: 10.1002/elps.201300019. Epub 2013 Sep 6. [PubMed:23857558 ]
Colorectal cancer
Qiu Y, Cai G, Su M, Chen T, Zheng X, Xu Y, Ni Y, Zhao A, Xu LX, Cai S, Jia W: Serum metabolite profiling of human colorectal cancer using GC-TOFMS and UPLC-QTOFMS. J Proteome Res. 2009 Oct;8(10):4844-50. doi: 10.1021/pr9004162. [PubMed:19678709 ] Ni Y, Xie G, Jia W: Metabonomics of human colorectal cancer: new approaches for early diagnosis and biomarker discovery. J Proteome Res. 2014 Sep 5;13(9):3857-70. doi: 10.1021/pr500443c. Epub 2014 Aug 14. [PubMed:25105552 ] Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ] Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ] Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Ovarian cancer
Zhang T, Wu X, Yin M, Fan L, Zhang H, Zhao F, Zhang W, Ke C, Zhang G, Hou Y, Zhou X, Lou G, Li K: Discrimination between malignant and benign ovarian tumors by plasma metabolomic profiling using ultra performance liquid chromatography/mass spectrometry. Clin Chim Acta. 2012 May 18;413(9-10):861-8. doi: 10.1016/j.cca.2012.01.026. Epub 2012 Jan 30. [PubMed:22309680 ]
Obesity
Simone Wahl, Christina Holzapfel, Zhonghao Yu, Michaela Breier, Ivan Kondofersky, Christiane Fuchs, Paula Singmann, Cornelia Prehn, Jerzy Adamski, Harald Grallert, Thomas Illig, Rui Wang-Sattler, Thomas Reinehr (2013). Metabolomics reveals determinants of weight loss during lifestyle intervention in obese children. Metabolomics.
Nicotinamide Adenine Dinucleotide Deficiency
Shi H, Enriquez A, Rapadas M, Martin EMMA, Wang R, Moreau J, Lim CK, Szot JO, Ip E, Hughes JN, Sugimoto K, Humphreys DT, McInerney-Leo AM, Leo PJ, Maghzal GJ, Halliday J, Smith J, Colley A, Mark PR, Collins F, Sillence DO, Winlaw DS, Ho JWK, Guillemin GJ, Brown MA, Kikuchi K, Thomas PQ, Stocker R, Giannoulatou E, Chapman G, Duncan EL, Sparrow DB, Dunwoodie SL: NAD Deficiency, Congenital Malformations, and Niacin Supplementation. N Engl J Med. 2017 Aug 10;377(6):544-552. doi: 10.1056/NEJMoa1616361. [PubMed:28792876 ]
Sepsis
Ferrario M, Cambiaghi A, Brunelli L, Giordano S, Caironi P, Guatteri L, Raimondi F, Gattinoni L, Latini R, Masson S, Ristagno G, Pastorelli R: Mortality prediction in patients with severe septic shock: a pilot study using a target metabolomics approach. Sci Rep. 2016 Feb 5;6:20391. doi: 10.1038/srep20391. [PubMed:26847922 ]
Hartnup disease
Jonas AJ, Butler IJ: Circumvention of defective neutral amino acid transport in Hartnup disease using tryptophan ethyl ester. J Clin Invest. 1989 Jul;84(1):200-4. [PubMed:2472426 ]
Leukemia
Peng CT, Wu KH, Lan SJ, Tsai JJ, Tsai FJ, Tsai CH: Amino acid concentrations in cerebrospinal fluid in children with acute lymphoblastic leukemia undergoing chemotherapy. Eur J Cancer. 2005 May;41(8):1158-63. Epub 2005 Apr 14. [PubMed:15911239 ]
Olivopontocerebral atrophy
Botez MI, Young SN: Biogenic amine metabolites and thiamine in cerebrospinal fluid in heredo-degenerative ataxias. Can J Neurol Sci. 2001 May;28(2):134-40. [PubMed:11383938 ]
Hereditary spastic paraplegia
Botez MI, Young SN: Biogenic amine metabolites and thiamine in cerebrospinal fluid in heredo-degenerative ataxias. Can J Neurol Sci. 2001 May;28(2):134-40. [PubMed:11383938 ]
Hypothyroidism
Sjoberg S, Eriksson M, Nordin C: L-thyroxine treatment and neurotransmitter levels in the cerebrospinal fluid of hypothyroid patients: a pilot study. Eur J Endocrinol. 1998 Nov;139(5):493-7. [PubMed:9849813 ]
Friedreich's ataxia
Botez MI, Young SN: Biogenic amine metabolites and thiamine in cerebrospinal fluid in heredo-degenerative ataxias. Can J Neurol Sci. 2001 May;28(2):134-40. [PubMed:11383938 ]
Celiac disease
Hallert C, Allenmark S, Larsson-Cohn U, Sedvall G: High level of pyridoxal 5'-phosphate in the cerebrospinal fluid of adult celiac patients. Am J Clin Nutr. 1982 Nov;36(5):851-4. [PubMed:6182788 ] Di Cagno R, De Angelis M, De Pasquale I, Ndagijimana M, Vernocchi P, Ricciuti P, Gagliardi F, Laghi L, Crecchio C, Guerzoni ME, Gobbetti M, Francavilla R: Duodenal and faecal microbiota of celiac children: molecular, phenotype and metabolome characterization. BMC Microbiol. 2011 Oct 4;11:219. doi: 10.1186/1471-2180-11-219. [PubMed:21970810 ] De Angelis M, Vannini L, Di Cagno R, Cavallo N, Minervini F, Francavilla R, Ercolini D, Gobbetti M: Salivary and fecal microbiota and metabolome of celiac children under gluten-free diet. Int J Food Microbiol. 2016 Dec 19;239:125-132. doi: 10.1016/j.ijfoodmicro.2016.07.025. Epub 2016 Jul 19. [PubMed:27452636 ]
Irritable bowel syndrome
Le Gall G, Noor SO, Ridgway K, Scovell L, Jamieson C, Johnson IT, Colquhoun IJ, Kemsley EK, Narbad A: Metabolomics of fecal extracts detects altered metabolic activity of gut microbiota in ulcerative colitis and irritable bowel syndrome. J Proteome Res. 2011 Sep 2;10(9):4208-18. doi: 10.1021/pr2003598. Epub 2011 Aug 8. [PubMed:21761941 ]
Ulcerative colitis
Le Gall G, Noor SO, Ridgway K, Scovell L, Jamieson C, Johnson IT, Colquhoun IJ, Kemsley EK, Narbad A: Metabolomics of fecal extracts detects altered metabolic activity of gut microbiota in ulcerative colitis and irritable bowel syndrome. J Proteome Res. 2011 Sep 2;10(9):4208-18. doi: 10.1021/pr2003598. Epub 2011 Aug 8. [PubMed:21761941 ] Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
Autism
De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]
Crohn's disease
Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
Rheumatoid arthritis
Tie-juan ShaoZhi-xing HeZhi-jun XieHai-chang LiMei-jiao WangCheng-ping Wen. Characterization of ankylosing spondylitis and rheumatoid arthritis using 1H NMR-based metabolomics of human fecal extracts. Metabolomics. April 2016, 12:70 [Link]
Perillyl alcohol administration for cancer treatment
Sugimoto M, Wong DT, Hirayama A, Soga T, Tomita M: Capillary electrophoresis mass spectrometry-based saliva metabolomics identified oral, breast and pancreatic cancer-specific profiles. Metabolomics. 2010 Mar;6(1):78-95. Epub 2009 Sep 10. [PubMed:20300169 ]
Pancreatic cancer
Sugimoto M, Wong DT, Hirayama A, Soga T, Tomita M: Capillary electrophoresis mass spectrometry-based saliva metabolomics identified oral, breast and pancreatic cancer-specific profiles. Metabolomics. 2010 Mar;6(1):78-95. Epub 2009 Sep 10. [PubMed:20300169 ]
Periodontal disease
Sugimoto M, Wong DT, Hirayama A, Soga T, Tomita M: Capillary electrophoresis mass spectrometry-based saliva metabolomics identified oral, breast and pancreatic cancer-specific profiles. Metabolomics. 2010 Mar;6(1):78-95. Epub 2009 Sep 10. [PubMed:20300169 ]
Frontotemporal dementia
Tsuruoka M, Hara J, Hirayama A, Sugimoto M, Soga T, Shankle WR, Tomita M: Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis. 2013 Oct;34(19):2865-72. doi: 10.1002/elps.201300019. Epub 2013 Sep 6. [PubMed:23857558 ]
Lewy body disease
Tsuruoka M, Hara J, Hirayama A, Sugimoto M, Soga T, Shankle WR, Tomita M: Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis. 2013 Oct;34(19):2865-72. doi: 10.1002/elps.201300019. Epub 2013 Sep 6. [PubMed:23857558 ]
Attachment loss
Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Periodontal Probing Depth
Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Cachexia
Wishart DS, Knox C, Guo AC, Eisner R, Young N, Gautam B, Hau DD, Psychogios N, Dong E, Bouatra S, Mandal R, Sinelnikov I, Xia J, Jia L, Cruz JA, Lim E, Sobsey CA, Shrivastava S, Huang P, Liu P, Fang L, Peng J, Fradette R, Cheng D, Tzur D, Clements M, Lewis A, De Souza A, Zuniga A, Dawe M, Xiong Y, Clive D, Greiner R, Nazyrova A, Shaykhutdinov R, Li L, Vogel HJ, Forsythe I: HMDB: a knowledgebase for the human metabolome. Nucleic Acids Res. 2009 Jan;37(Database issue):D603-10. doi: 10.1093/nar/gkn810. Epub 2008 Oct 25. [PubMed:18953024 ]
Eosinophilic esophagitis
Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Tryptophanuria with dwarfism
TADA K, ITO H, WADA Y, ARAKAWA T: CONGENITAL TRYPTOPHANURIA WITH DWARFISM ("H" DISEASE-LIKE CLINICAL FEATURES WITHOUT INDICANURIA AND GENERALIZED AMINOACIDURIA):--A PROBABLY NEW INBORN ERROR OF TRYPTOPHAN METABOLISM. Tohoku J Exp Med. 1963 Jul 25;80:118-34. [PubMed:14055140 ]

Associated OMIM IDs

181500 (Schizophrenia)
104300 (Alzheimer's disease)
114500 (Colorectal cancer)
167000 (Ovarian cancer)
601665 (Obesity)
234500 (Hartnup disease)
182601 (Hereditary spastic paraplegia)
229300 (Friedreich's ataxia)
212750 (Celiac disease)
209850 (Autism)
266600 (Crohn's disease)
180300 (Rheumatoid arthritis)
260350 (Pancreatic cancer)
170650 (Periodontal disease)
600274 (Frontotemporal dementia)
610247 (Eosinophilic esophagitis)
276100 (Tryptophanuria with dwarfism)

External Links

DrugBank ID

DB00150

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

16828

Food Biomarker Ontology

Not Available

VMH ID

TRP_L

MarkerDB ID

MDB00000284

Good Scents ID

Not Available

References

Synthesis Reference

Amir-Heidari, Bagher; Thirlway, Jenny; Micklefield, Jason. Stereochemical course of tryptophan dehydrogenation during biosynthesis of the calcium-dependent lipopeptide antibiotics. Organic Letters (2007), 9(8), 1513-1516.

Material Safety Data Sheet (MSDS)

Not Available

General References

Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
Sjoberg S, Eriksson M, Nordin C: L-thyroxine treatment and neurotransmitter levels in the cerebrospinal fluid of hypothyroid patients: a pilot study. Eur J Endocrinol. 1998 Nov;139(5):493-7. [PubMed:9849813 ]
Eklundh T, Eriksson M, Sjoberg S, Nordin C: Monoamine precursors, transmitters and metabolites in cerebrospinal fluid: a prospective study in healthy male subjects. J Psychiatr Res. 1996 May-Jun;30(3):201-8. [PubMed:8884658 ]
Peng CT, Wu KH, Lan SJ, Tsai JJ, Tsai FJ, Tsai CH: Amino acid concentrations in cerebrospinal fluid in children with acute lymphoblastic leukemia undergoing chemotherapy. Eur J Cancer. 2005 May;41(8):1158-63. Epub 2005 Apr 14. [PubMed:15911239 ]
Cynober LA: Plasma amino acid levels with a note on membrane transport: characteristics, regulation, and metabolic significance. Nutrition. 2002 Sep;18(9):761-6. [PubMed:12297216 ]
Rainesalo S, Keranen T, Palmio J, Peltola J, Oja SS, Saransaari P: Plasma and cerebrospinal fluid amino acids in epileptic patients. Neurochem Res. 2004 Jan;29(1):319-24. [PubMed:14992292 ]
Buczko W, Cylwik D, Stokowska W: [Metabolism of tryptophan via the kynurenine pathway in saliva]. Postepy Hig Med Dosw (Online). 2005;59:283-9. [PubMed:15995595 ]
Heyes MP, Saito K, Crowley JS, Davis LE, Demitrack MA, Der M, Dilling LA, Elia J, Kruesi MJ, Lackner A, et al.: Quinolinic acid and kynurenine pathway metabolism in inflammatory and non-inflammatory neurological disease. Brain. 1992 Oct;115 ( Pt 5):1249-73. [PubMed:1422788 ]
Koskiniemi M, Laakso J, Kuurne T, Laipio M, Harkonen M: Indole levels in human lumbar and ventricular cerebrospinal fluid and the effect of L-tryptophan administration. Acta Neurol Scand. 1985 Feb;71(2):127-32. [PubMed:2580417 ]
Jonas AJ, Butler IJ: Circumvention of defective neutral amino acid transport in Hartnup disease using tryptophan ethyl ester. J Clin Invest. 1989 Jul;84(1):200-4. [PubMed:2472426 ]
Guchhait RB, Janson C, Price WH: Validity of plasma factor in schizophrenia as measured by tryptophan uptake. Biol Psychiatry. 1975 Jun;10(3):303-14. [PubMed:49200 ]
Kennedy JS, Gwirtsman HE, Schmidt DE, Johnson BW, Fielstein E, Salomon RM, Shiavi RG, Ebert MH, Parris WC, Loosen PT: Serial cerebrospinal fluid tryptophan and 5-hydroxy indoleacetic acid concentrations in healthy human subjects. Life Sci. 2002 Aug 23;71(14):1703-15. [PubMed:12137916 ]
Bender KI, Lutsevich NF, Lutsevich AN, Kupchikov VV: [Endogenous metabolites as modulators of the transport of drugs by serum albumin]. Farmakol Toksikol. 1990 May-Jun;53(3):72-80. [PubMed:2201566 ]
Heiman-Patterson TD, Bird SJ, Parry GJ, Varga J, Shy ME, Culligan NW, Edelsohn L, Tatarian GT, Heyes MP, Garcia CA, et al.: Peripheral neuropathy associated with eosinophilia-myalgia syndrome. Ann Neurol. 1990 Oct;28(4):522-8. [PubMed:2174666 ]
Talbert AM, Tranter GE, Holmes E, Francis PL: Determination of drug-plasma protein binding kinetics and equilibria by chromatographic profiling: exemplification of the method using L-tryptophan and albumin. Anal Chem. 2002 Jan 15;74(2):446-52. [PubMed:11811421 ]
Dunner DL, Heiber S, Perel JM: The effect of L-tryptophan administration on the concentration of probenecid in plasma and cerebrospinal fluid in patients. Psychopharmacology (Berl). 1977 Aug 16;53(3):305-8. [PubMed:408860 ]
George CF, Millar TW, Hanly PJ, Kryger MH: The effect of L-tryptophan on daytime sleep latency in normals: correlation with blood levels. Sleep. 1989 Aug;12(4):345-53. [PubMed:2669092 ]
Gutsche B, Grun C, Scheutzow D, Herderich M: Tryptophan glycoconjugates in food and human urine. Biochem J. 1999 Oct 1;343 Pt 1:11-9. [PubMed:10493906 ]
Milburn DS, Myers CW: Tryptophan toxicity: a pharmacoepidemiologic review of eosinophilia-myalgia syndrome. DICP. 1991 Nov;25(11):1259-62. [PubMed:1763543 ]
Gross B, Ronen N, Honigman S, Livne E: Tryptophan toxicity--time and dose response in rats. Adv Exp Med Biol. 1999;467:507-16. [PubMed:10721094 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
Mehraj V, Routy JP: Tryptophan Catabolism in Chronic Viral Infections: Handling Uninvited Guests. Int J Tryptophan Res. 2015 Aug 4;8:41-8. doi: 10.4137/IJTR.S26862. eCollection 2015. [PubMed:26309411 ]
Lionetto L, Ulivieri M, Capi M, De Bernardini D, Fazio F, Petrucca A, Pomes LM, De Luca O, Gentile G, Casolla B, Curto M, Salerno G, Schillizzi S, Torre MS, Santino I, Rocco M, Marchetti P, Aceti A, Ricci A, Bonfini R, Nicoletti F, Simmaco M, Borro M: Increased kynurenine-to-tryptophan ratio in the serum of patients infected with SARS-CoV2: An observational cohort study. Biochim Biophys Acta Mol Basis Dis. 2021 Mar 1;1867(3):166042. doi: 10.1016/j.bbadis.2020.166042. Epub 2020 Dec 16. [PubMed:33338598 ]
Darcy CJ, Davis JS, Woodberry T, McNeil YR, Stephens DP, Yeo TW, Anstey NM: An observational cohort study of the kynurenine to tryptophan ratio in sepsis: association with impaired immune and microvascular function. PLoS One. 2011;6(6):e21185. doi: 10.1371/journal.pone.0021185. Epub 2011 Jun 22. [PubMed:21731667 ]

Only showing the first 10 proteins. There are 11 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Aromatic-L-amino-acid decarboxylase

General function:: Involved in carboxy-lyase activity
Specific function:: Catalyzes the decarboxylation of L-3,4-dihydroxyphenylalanine (DOPA) to dopamine, L-5-hydroxytryptophan to serotonin and L-tryptophan to tryptamine.
Gene Name:: DDC
Uniprot ID:: P20711
Molecular weight:: 53893.755

Reactions

L-Tryptophan → Tryptamine + Carbon dioxide	details

References

Tyce GM: Origin and metabolism of serotonin. J Cardiovasc Pharmacol. 1990;16 Suppl 3:S1-7. [PubMed:1369709 ]

Enzyme Details

2. Indoleamine 2,3-dioxygenase 1

General function:: Involved in heme binding
Specific function:: Catalyzes the cleavage of the pyrrol ring of tryptophan and incorporates both atoms of a molecule of oxygen.
Gene Name:: IDO1
Uniprot ID:: P14902
Molecular weight:: 45325.89

Reactions

L-Tryptophan + Oxygen → L-Formylkynurenine	details

References

Agaugue S, Perrin-Cocon L, Coutant F, Andre P, Lotteau V: 1-Methyl-tryptophan can interfere with TLR signaling in dendritic cells independently of IDO activity. J Immunol. 2006 Aug 15;177(4):2061-71. [PubMed:16887964 ]
Fallarino F, Gizzi S, Mosci P, Grohmann U, Puccetti P: Tryptophan catabolism in IDO+ plasmacytoid dendritic cells. Curr Drug Metab. 2007 Apr;8(3):209-16. [PubMed:17430109 ]
Cozzi A, Zignego AL, Carpendo R, Biagiotti T, Aldinucci A, Monti M, Giannini C, Rosselli M, Laffi G, Moroni F: Low serum tryptophan levels, reduced macrophage IDO activity and high frequency of psychopathology in HCV patients. J Viral Hepat. 2006 Jun;13(6):402-8. [PubMed:16842443 ]
Grohmann U, Volpi C, Fallarino F, Bozza S, Bianchi R, Vacca C, Orabona C, Belladonna ML, Ayroldi E, Nocentini G, Boon L, Bistoni F, Fioretti MC, Romani L, Riccardi C, Puccetti P: Reverse signaling through GITR ligand enables dexamethasone to activate IDO in allergy. Nat Med. 2007 May;13(5):579-86. Epub 2007 Apr 8. [PubMed:17417651 ]
Zheng X, Koropatnick J, Li M, Zhang X, Ling F, Ren X, Hao X, Sun H, Vladau C, Franek JA, Feng B, Urquhart BL, Zhong R, Freeman DJ, Garcia B, Min WP: Reinstalling antitumor immunity by inhibiting tumor-derived immunosuppressive molecule IDO through RNA interference. J Immunol. 2006 Oct 15;177(8):5639-46. [PubMed:17015752 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Rafice SA, Chauhan N, Efimov I, Basran J, Raven EL: Oxidation of L-tryptophan in biology: a comparison between tryptophan 2,3-dioxygenase and indoleamine 2,3-dioxygenase. Biochem Soc Trans. 2009 Apr;37(Pt 2):408-12. doi: 10.1042/BST0370408. [PubMed:19290871 ]

Enzyme Details

3. Tryptophan 5-hydroxylase 1

General function:: Involved in amino acid binding
Specific function:: Not Available
Gene Name:: TPH1
Uniprot ID:: P17752
Molecular weight:: 50984.725

Reactions

L-Tryptophan + Tetrahydrobiopterin + Oxygen → 5-Hydroxy-L-tryptophan + 4a-Hydroxytetrahydrobiopterin	details
Tetrahydrobiopterin + L-Tryptophan + Oxygen → 5-Hydroxy-L-tryptophan + 4a-Carbinolamine tetrahydrobiopterin + Water	details

References

Pavon JA, Fitzpatrick PF: Insights into the catalytic mechanisms of phenylalanine and tryptophan hydroxylase from kinetic isotope effects on aromatic hydroxylation. Biochemistry. 2006 Sep 12;45(36):11030-7. [PubMed:16953590 ]
Langfort J, Baranczuk E, Pawlak D, Chalimoniuk M, Lukacova N, Marsala J, Gorski J: The effect of endurance training on regional serotonin metabolism in the brain during early stage of detraining period in the female rat. Cell Mol Neurobiol. 2006 Oct-Nov;26(7-8):1327-42. Epub 2006 Aug 1. [PubMed:16897368 ]
Nakamura K, Hasegawa H: Developmental role of tryptophan hydroxylase in the nervous system. Mol Neurobiol. 2007 Feb;35(1):45-54. [PubMed:17519505 ]
Invernizzi RW: Role of TPH-2 in brain function: news from behavioral and pharmacologic studies. J Neurosci Res. 2007 Nov 1;85(14):3030-5. [PubMed:17492791 ]
Neckameyer WS, Coleman CM, Eadie S, Goodwin SF: Compartmentalization of neuronal and peripheral serotonin synthesis in Drosophila melanogaster. Genes Brain Behav. 2007 Nov;6(8):756-69. Epub 2007 Mar 21. [PubMed:17376153 ]

Enzyme Details

4. Tryptophan 5-hydroxylase 2

General function:: Involved in amino acid binding
Specific function:: Not Available
Gene Name:: TPH2
Uniprot ID:: Q8IWU9
Molecular weight:: 56056.295

Reactions

L-Tryptophan + Tetrahydrobiopterin + Oxygen → 5-Hydroxy-L-tryptophan + 4a-Hydroxytetrahydrobiopterin	details
Tetrahydrobiopterin + L-Tryptophan + Oxygen → 5-Hydroxy-L-tryptophan + 4a-Carbinolamine tetrahydrobiopterin + Water	details

References

Lopez VA, Detera-Wadleigh S, Cardona I, Kassem L, McMahon FJ: Nested association between genetic variation in tryptophan hydroxylase II, bipolar affective disorder, and suicide attempts. Biol Psychiatry. 2007 Jan 15;61(2):181-6. Epub 2006 Jun 27. [PubMed:16806105 ]
Kraus MR, Al-Taie O, Schafer A, Pfersdorff M, Lesch KP, Scheurlen M: Serotonin-1A receptor gene HTR1A variation predicts interferon-induced depression in chronic hepatitis C. Gastroenterology. 2007 Apr;132(4):1279-86. Epub 2007 Feb 25. [PubMed:17408646 ]
Nakamura K, Hasegawa H: Developmental role of tryptophan hydroxylase in the nervous system. Mol Neurobiol. 2007 Feb;35(1):45-54. [PubMed:17519505 ]
Invernizzi RW: Role of TPH-2 in brain function: news from behavioral and pharmacologic studies. J Neurosci Res. 2007 Nov 1;85(14):3030-5. [PubMed:17492791 ]
Calcagno E, Canetta A, Guzzetti S, Cervo L, Invernizzi RW: Strain differences in basal and post-citalopram extracellular 5-HT in the mouse medial prefrontal cortex and dorsal hippocampus: relation with tryptophan hydroxylase-2 activity. J Neurochem. 2007 Nov;103(3):1111-20. Epub 2007 Jul 31. [PubMed:17666043 ]

Enzyme Details

5. Tryptophan--tRNA ligase, cytoplasmic

General function:: Involved in nucleotide binding
Specific function:: Isoform 1, isoform 2 and T1-TrpRS have aminoacylation activity while T2-TrpRS lacks it. Isoform 2, T1-TrpRS and T2-TrpRS possess angiostatic activity whereas isoform 1 lacks it. T2-TrpRS inhibits fluid shear stress-activated responses of endothelial cells. Regulates ERK, Akt, and eNOS activation pathways that are associated with angiogenesis, cytoskeletal reorganization and shear stress-responsive gene expression.
Gene Name:: WARS
Uniprot ID:: P23381
Molecular weight:: 53164.91

Reactions

Adenosine triphosphate + L-Tryptophan + tRNA(Trp) → Adenosine monophosphate + Pyrophosphate + L-tryptophyl-tRNA(Trp)	details
Adenosine triphosphate + L-Tryptophan + tRNA(Trp) → Adenosine monophosphate + Pyrophosphate + L-Tryptophanyl-tRNA(Trp)	details

References

Tsuchiya W, Umehara T, Kuno A, Hasegawa T: Determination of tryptophan tRNA recognition sites for tryptophanyl-tRNA synthetase from hyperthermophilic archaeon, Aeropyrum pernix K1. Nucleic Acids Symp Ser (Oxf). 2004;(48):185-6. [PubMed:17150540 ]
Retailleau P, Weinreb V, Hu M, Carter CW Jr: Crystal structure of tryptophanyl-tRNA synthetase complexed with adenosine-5' tetraphosphate: evidence for distributed use of catalytic binding energy in amino acid activation by class I aminoacyl-tRNA synthetases. J Mol Biol. 2007 May 25;369(1):108-28. Epub 2007 Mar 12. [PubMed:17428498 ]
Zhu L, Ji F, Wang Y, Zhang Y, Liu Q, Zhang JZ, Matsushima K, Cao Q, Zhang Y: Synovial autoreactive T cells in rheumatoid arthritis resist IDO-mediated inhibition. J Immunol. 2006 Dec 1;177(11):8226-33. [PubMed:17114500 ]
Yadav MC, Burudi EM, Alirezaei M, Flynn CC, Watry DD, Lanigan CM, Fox HS: IFN-gamma-induced IDO and WRS expression in microglia is differentially regulated by IL-4. Glia. 2007 Oct;55(13):1385-96. [PubMed:17661345 ]
Yang XL, Otero FJ, Ewalt KL, Liu J, Swairjo MA, Kohrer C, RajBhandary UL, Skene RJ, McRee DE, Schimmel P: Two conformations of a crystalline human tRNA synthetase-tRNA complex: implications for protein synthesis. EMBO J. 2006 Jun 21;25(12):2919-29. Epub 2006 May 25. [PubMed:16724112 ]

Enzyme Details

6. Tryptophan--tRNA ligase, mitochondrial

General function:: Involved in nucleotide binding
Specific function:: Not Available
Gene Name:: WARS2
Uniprot ID:: Q9UGM6
Molecular weight:: 40146.265

Reactions

Adenosine triphosphate + L-Tryptophan + tRNA(Trp) → Adenosine monophosphate + Pyrophosphate + L-tryptophyl-tRNA(Trp)	details
Adenosine triphosphate + L-Tryptophan + tRNA(Trp) → Adenosine monophosphate + Pyrophosphate + L-Tryptophanyl-tRNA(Trp)	details

References

Paley EL, Denisova G, Sokolova O, Posternak N, Wang X, Brownell AL: Tryptamine induces tryptophanyl-tRNA synthetase-mediated neurodegeneration with neurofibrillary tangles in human cell and mouse models. Neuromolecular Med. 2007;9(1):55-82. [PubMed:17114825 ]
Retailleau P, Weinreb V, Hu M, Carter CW Jr: Crystal structure of tryptophanyl-tRNA synthetase complexed with adenosine-5' tetraphosphate: evidence for distributed use of catalytic binding energy in amino acid activation by class I aminoacyl-tRNA synthetases. J Mol Biol. 2007 May 25;369(1):108-28. Epub 2007 Mar 12. [PubMed:17428498 ]
Banin E, Dorrell MI, Aguilar E, Ritter MR, Aderman CM, Smith AC, Friedlander J, Friedlander M: T2-TrpRS inhibits preretinal neovascularization and enhances physiological vascular regrowth in OIR as assessed by a new method of quantification. Invest Ophthalmol Vis Sci. 2006 May;47(5):2125-34. [PubMed:16639024 ]
Yang XL, Otero FJ, Ewalt KL, Liu J, Swairjo MA, Kohrer C, RajBhandary UL, Skene RJ, McRee DE, Schimmel P: Two conformations of a crystalline human tRNA synthetase-tRNA complex: implications for protein synthesis. EMBO J. 2006 Jun 21;25(12):2919-29. Epub 2006 May 25. [PubMed:16724112 ]
Charriere F, Helgadottir S, Horn EK, Soll D, Schneider A: Dual targeting of a single tRNA(Trp) requires two different tryptophanyl-tRNA synthetases in Trypanosoma brucei. Proc Natl Acad Sci U S A. 2006 May 2;103(18):6847-52. Epub 2006 Apr 24. [PubMed:16636268 ]

Enzyme Details

7. Tryptophan 2,3-dioxygenase

General function:: Involved in tryptophan 2,3-dioxygenase activity
Specific function:: Incorporates oxygen into the indole moiety of tryptophan. Has a broad specificity towards tryptamine and derivatives including D- and L-tryptophan, 5-hydroxytryptophan and serotonin (By similarity).
Gene Name:: TDO2
Uniprot ID:: P48775
Molecular weight:: 47871.215

Reactions

L-Tryptophan + Oxygen → L-Formylkynurenine	details

References

Rafice SA, Chauhan N, Efimov I, Basran J, Raven EL: Oxidation of L-tryptophan in biology: a comparison between tryptophan 2,3-dioxygenase and indoleamine 2,3-dioxygenase. Biochem Soc Trans. 2009 Apr;37(Pt 2):408-12. doi: 10.1042/BST0370408. [PubMed:19290871 ]

Enzyme Details

8. Indoleamine 2,3-dioxygenase 2

General function:: Involved in heme binding
Specific function:: Catalyzes the first and rate-limiting step in the kynurenine pathway of tryptophan catabolism.
Gene Name:: IDO2
Uniprot ID:: Q6ZQW0
Molecular weight:: 47074.745

Reactions

L-Tryptophan + Oxygen → L-Formylkynurenine	details

Enzyme Details

9. L-amino-acid oxidase

General function:: Involved in oxidoreductase activity
Specific function:: Lysosomal L-amino-acid oxidase with highest specific activity with phenylalanine. May play a role in lysosomal antigen processing and presentation (By similarity).
Gene Name:: IL4I1
Uniprot ID:: Q96RQ9
Molecular weight:: 65327.26

Reactions

L-Tryptophan + Water + Oxygen → Indolepyruvate + Ammonia + Hydrogen peroxide	details

Transporters

Enzyme Details

1. Monocarboxylate transporter 8

General function:: Involved in transmembrane transport
Specific function:: Very active and specific thyroid hormone transporter. Stimulates cellular uptake of thyroxine (T4), triiodothyronine (T3), reverse triiodothyronine (rT3) and diidothyronine. Does not transport Leu, Phe, Trp or Tyr
Gene Name:: SLC16A2
Uniprot ID:: P36021
Molecular weight:: 59510.9

References

Friesema EC, Ganguly S, Abdalla A, Manning Fox JE, Halestrap AP, Visser TJ: Identification of monocarboxylate transporter 8 as a specific thyroid hormone transporter. J Biol Chem. 2003 Oct 10;278(41):40128-35. Epub 2003 Jul 18. [PubMed:12871948 ]

Enzyme Details

2. Monocarboxylate transporter 10

General function:: Involved in transmembrane transport
Specific function:: Sodium-independent transporter that mediates the update of aromatic acid. Can function as a net efflux pathway for aromatic amino acids in the basosolateral epithelial cells
Gene Name:: SLC16A10
Uniprot ID:: Q8TF71
Molecular weight:: 55492.1

References

Kim DK, Kanai Y, Matsuo H, Kim JY, Chairoungdua A, Kobayashi Y, Enomoto A, Cha SH, Goya T, Endou H: The human T-type amino acid transporter-1: characterization, gene organization, and chromosomal location. Genomics. 2002 Jan;79(1):95-103. [PubMed:11827462 ]
Kim DK, Kanai Y, Chairoungdua A, Matsuo H, Cha SH, Endou H: Expression cloning of a Na+-independent aromatic amino acid transporter with structural similarity to H+/monocarboxylate transporters. J Biol Chem. 2001 May 18;276(20):17221-8. Epub 2001 Feb 20. [PubMed:11278508 ]

Only showing the first 10 proteins. There are 11 proteins in total.

Show all enzymes and transporters

Showing metabocard for L-Tryptophan (HMDB0000929)

MOL for HMDB0000929 (L-Tryptophan)

3D MOL for HMDB0000929 (L-Tryptophan)

3D SDF for HMDB0000929 (L-Tryptophan)

3D-SDF for HMDB0000929 (L-Tryptophan)

PDB for HMDB0000929 (L-Tryptophan)

3D PDB for HMDB0000929 (L-Tryptophan)

SMILES for HMDB0000929 (L-Tryptophan)

INCHI for HMDB0000929 (L-Tryptophan)

Structure for HMDB0000929 (L-Tryptophan)

3D Structure for HMDB0000929 (L-Tryptophan)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

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