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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-07-07 20:53:57 UTC
HMDB IDHMDB0000684
Secondary Accession Numbers
  • HMDB0000183
  • HMDB00183
  • HMDB00684
Metabolite Identification
Common NameKynurenine
DescriptionL-Kynurenine, which is also known as Kynurenine or 3-Anthraniloylalanine, belongs to the class of compounds known as alkyl-phenylketones. Alkyl-phenylketones are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.  Kynurenine is a metabolite of the amino acid L-tryptophan and is used in the production of niacin. Specifically, kynurenine is synthesized by the enzyme tryptophan dioxygenase, which is made primarily but not exclusively in the liver. Kynurenine is also synthesized by indoleamine 2,3-dioxygenase (IDO), which is found in many tissues and is often overexpressed in response to immune activation. Kynurenine and its other tryptophan breakdown products (Trp catabolites) carry out a wide range of biological functions, including dilating blood vessels during inflammation (PMID: 20190767 ) and regulating the immune response (PMID: 21041655 ). Kynurenine is the precursor to the neuroprotective agent known as kynurenic acid. Kynurenine is also the precursor to the neurotoxic agent quinolinic acid. Dysregulation in the balance between these two kynurenine derivatives can be observable in many disorders such as stroke, epilepsy, multiple sclerosis, and amyotrophic lateral sclerosis. Blood levels of kynurenine are reduced in people with bipolar disorder (PMID: 33077852 ) and schizophrenia (PMID: 21727251 ). On the other hand, kynurenine production is increased in Alzheimer's disease (PMID: 16008823 ). and cardiovascular disease (PMID: 12814390 ), where its metabolites are associated with cognitive deficits (PMID: 20639188 ) and depressive symptoms. Kynurenine and its precursor (tryptophan) also play important roles in regulating inflammation and the immune responses to infectious organisms. 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 to kynurenine by the enzyme known as indoleamine-2,3-dioxygenase (IDO) which is induced by interferon gamma (IFN-gamma or IFNG). Kynurenine activates the aryl hydrocarbon receptor (AhR), which plays a key role immune suppression. The role of IDO 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 by kynurenine leads to a state of immunosuppression and is intended to serve as a brake on the immune response to the infectious organisms (overexpression of IFNG and IL-1B).  Unfortunately, tryptophan starvation is often not effective against viruses or even all infectious microbes. As a result, this AhR activation by kynurenine 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 or KT 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 ). Kynurenine and its metabolites are also known as uremic toxins (PMID: 12092667 ). Chronically high levels of uremic toxins are known to cause damage to kidneys, liver, heart and the brain. Serum albumin binds to most uremic toxins quite strongly and can act as a first line of defense against transient rises in these compounds.
Structure
Data?1676999703
Synonyms
ValueSource
(2S)-2-Amino-4-(2-aminophenyl)-4-oxobutanoic acidChEBI
3-Anthraniloyl-L-alanineChEBI
KYNURENINEChEBI
(2S)-2-Amino-4-(2-aminophenyl)-4-oxobutanoateGenerator
(S)-alpha,2-Diamino-3-hydroxy-gamma-oxo-benzenebutanoateHMDB
(S)-alpha,2-Diamino-3-hydroxy-gamma-oxo-benzenebutanoic acidHMDB
3-Anthraniloyl-alanineHMDB
3-AnthraniloylalanineHMDB
alpha,2-Diamino-gamma-oxo-benzenebutanoateHMDB
alpha,2-Diamino-gamma-oxo-benzenebutanoic acidHMDB
DL-KynurenineHMDB
KynureninHMDB
QuinurenineHMDB
L-KynurenineHMDB
3-(2-aminobenzoyl)-L-alanineHMDB
KYNAHMDB
Chemical FormulaC10H12N2O3
Average Molecular Weight208.2139
Monoisotopic Molecular Weight208.08479226
IUPAC Name(2S)-2-amino-4-(2-aminophenyl)-4-oxobutanoic acid
Traditional NameL-kynurenine
CAS Registry Number2922-83-0
SMILES
N[C@@H](CC(=O)C1=CC=CC=C1N)C(O)=O
InChI Identifier
InChI=1S/C10H12N2O3/c11-7-4-2-1-3-6(7)9(13)5-8(12)10(14)15/h1-4,8H,5,11-12H2,(H,14,15)/t8-/m0/s1
InChI KeyYGPSJZOEDVAXAB-QMMMGPOBSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAlkyl-phenylketones
Alternative Parents
Substituents
  • Alkyl-phenylketone
  • Butyrophenone
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • L-alpha-amino acid
  • Benzoyl
  • Gamma-keto acid
  • Aniline or substituted anilines
  • Aryl alkyl ketone
  • Monocyclic benzene moiety
  • Beta-aminoketone
  • Keto acid
  • Benzenoid
  • Vinylogous amide
  • Amino acid
  • Amino acid or derivatives
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Primary aliphatic amine
  • Amine
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxide
  • Organic nitrogen compound
  • Organonitrogen compound
  • Primary amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect
Disposition
Biological locationRoute of exposureSource
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point191 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+MetCCS_train_pos149.05930932474
[M+H]+Not Available149.3http://allccs.zhulab.cn/database/detail?ID=AllCCS00000515
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.67 g/LALOGPS
logP-1.9ALOGPS
logP-1.9ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)1.19ChemAxon
pKa (Strongest Basic)8.96ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area106.41 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity55.05 m³·mol⁻¹ChemAxon
Polarizability20.59 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+148.69931661259
DarkChem[M-H]-146.27131661259
AllCCS[M+H]+146.93732859911
AllCCS[M-H]-144.92632859911
DeepCCS[M+H]+144.25930932474
DeepCCS[M-H]-141.86430932474
DeepCCS[M-2H]-175.56930932474
DeepCCS[M+Na]+150.26230932474
AllCCS[M+H]+146.932859911
AllCCS[M+H-H2O]+143.032859911
AllCCS[M+NH4]+150.632859911
AllCCS[M+Na]+151.732859911
AllCCS[M-H]-144.932859911
AllCCS[M+Na-2H]-145.432859911
AllCCS[M+HCOO]-146.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
L-KynurenineN[C@@H](CC(=O)C1=CC=CC=C1N)C(O)=O3267.7Standard polar33892256
L-KynurenineN[C@@H](CC(=O)C1=CC=CC=C1N)C(O)=O1988.3Standard non polar33892256
L-KynurenineN[C@@H](CC(=O)C1=CC=CC=C1N)C(O)=O2180.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
L-Kynurenine,1TMS,isomer #1C[Si](C)(C)OC(=O)[C@@H](N)CC(=O)C1=CC=CC=C1N2063.8Semi standard non polar33892256
L-Kynurenine,1TMS,isomer #2C[Si](C)(C)N[C@@H](CC(=O)C1=CC=CC=C1N)C(=O)O2111.3Semi standard non polar33892256
L-Kynurenine,1TMS,isomer #3C[Si](C)(C)NC1=CC=CC=C1C(=O)C[C@H](N)C(=O)O2162.4Semi standard non polar33892256
L-Kynurenine,2TMS,isomer #1C[Si](C)(C)N[C@@H](CC(=O)C1=CC=CC=C1N)C(=O)O[Si](C)(C)C2096.5Semi standard non polar33892256
L-Kynurenine,2TMS,isomer #1C[Si](C)(C)N[C@@H](CC(=O)C1=CC=CC=C1N)C(=O)O[Si](C)(C)C2129.6Standard non polar33892256
L-Kynurenine,2TMS,isomer #1C[Si](C)(C)N[C@@H](CC(=O)C1=CC=CC=C1N)C(=O)O[Si](C)(C)C2993.1Standard polar33892256
L-Kynurenine,2TMS,isomer #2C[Si](C)(C)NC1=CC=CC=C1C(=O)C[C@H](N)C(=O)O[Si](C)(C)C2135.3Semi standard non polar33892256
L-Kynurenine,2TMS,isomer #2C[Si](C)(C)NC1=CC=CC=C1C(=O)C[C@H](N)C(=O)O[Si](C)(C)C2180.7Standard non polar33892256
L-Kynurenine,2TMS,isomer #2C[Si](C)(C)NC1=CC=CC=C1C(=O)C[C@H](N)C(=O)O[Si](C)(C)C2878.8Standard polar33892256
L-Kynurenine,2TMS,isomer #3C[Si](C)(C)NC1=CC=CC=C1C(=O)C[C@H](N[Si](C)(C)C)C(=O)O2191.3Semi standard non polar33892256
L-Kynurenine,2TMS,isomer #3C[Si](C)(C)NC1=CC=CC=C1C(=O)C[C@H](N[Si](C)(C)C)C(=O)O2195.0Standard non polar33892256
L-Kynurenine,2TMS,isomer #3C[Si](C)(C)NC1=CC=CC=C1C(=O)C[C@H](N[Si](C)(C)C)C(=O)O2855.4Standard polar33892256
L-Kynurenine,2TMS,isomer #4C[Si](C)(C)N([C@@H](CC(=O)C1=CC=CC=C1N)C(=O)O)[Si](C)(C)C2207.2Semi standard non polar33892256
L-Kynurenine,2TMS,isomer #4C[Si](C)(C)N([C@@H](CC(=O)C1=CC=CC=C1N)C(=O)O)[Si](C)(C)C2264.8Standard non polar33892256
L-Kynurenine,2TMS,isomer #4C[Si](C)(C)N([C@@H](CC(=O)C1=CC=CC=C1N)C(=O)O)[Si](C)(C)C3148.5Standard polar33892256
L-Kynurenine,2TMS,isomer #5C[Si](C)(C)N(C1=CC=CC=C1C(=O)C[C@H](N)C(=O)O)[Si](C)(C)C2124.7Semi standard non polar33892256
L-Kynurenine,2TMS,isomer #5C[Si](C)(C)N(C1=CC=CC=C1C(=O)C[C@H](N)C(=O)O)[Si](C)(C)C2284.3Standard non polar33892256
L-Kynurenine,2TMS,isomer #5C[Si](C)(C)N(C1=CC=CC=C1C(=O)C[C@H](N)C(=O)O)[Si](C)(C)C3147.7Standard polar33892256
L-Kynurenine,3TMS,isomer #1C[Si](C)(C)NC1=CC=CC=C1C(=O)C[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C2195.7Semi standard non polar33892256
L-Kynurenine,3TMS,isomer #1C[Si](C)(C)NC1=CC=CC=C1C(=O)C[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C2192.8Standard non polar33892256
L-Kynurenine,3TMS,isomer #1C[Si](C)(C)NC1=CC=CC=C1C(=O)C[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C2572.7Standard polar33892256
L-Kynurenine,3TMS,isomer #2C[Si](C)(C)OC(=O)[C@H](CC(=O)C1=CC=CC=C1N)N([Si](C)(C)C)[Si](C)(C)C2247.5Semi standard non polar33892256
L-Kynurenine,3TMS,isomer #2C[Si](C)(C)OC(=O)[C@H](CC(=O)C1=CC=CC=C1N)N([Si](C)(C)C)[Si](C)(C)C2262.4Standard non polar33892256
L-Kynurenine,3TMS,isomer #2C[Si](C)(C)OC(=O)[C@H](CC(=O)C1=CC=CC=C1N)N([Si](C)(C)C)[Si](C)(C)C2889.3Standard polar33892256
L-Kynurenine,3TMS,isomer #3C[Si](C)(C)OC(=O)[C@@H](N)CC(=O)C1=CC=CC=C1N([Si](C)(C)C)[Si](C)(C)C2105.8Semi standard non polar33892256
L-Kynurenine,3TMS,isomer #3C[Si](C)(C)OC(=O)[C@@H](N)CC(=O)C1=CC=CC=C1N([Si](C)(C)C)[Si](C)(C)C2289.6Standard non polar33892256
L-Kynurenine,3TMS,isomer #3C[Si](C)(C)OC(=O)[C@@H](N)CC(=O)C1=CC=CC=C1N([Si](C)(C)C)[Si](C)(C)C2673.6Standard polar33892256
L-Kynurenine,3TMS,isomer #4C[Si](C)(C)N[C@@H](CC(=O)C1=CC=CC=C1N([Si](C)(C)C)[Si](C)(C)C)C(=O)O2156.4Semi standard non polar33892256
L-Kynurenine,3TMS,isomer #4C[Si](C)(C)N[C@@H](CC(=O)C1=CC=CC=C1N([Si](C)(C)C)[Si](C)(C)C)C(=O)O2300.8Standard non polar33892256
L-Kynurenine,3TMS,isomer #4C[Si](C)(C)N[C@@H](CC(=O)C1=CC=CC=C1N([Si](C)(C)C)[Si](C)(C)C)C(=O)O2646.9Standard polar33892256
L-Kynurenine,3TMS,isomer #5C[Si](C)(C)NC1=CC=CC=C1C(=O)C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C2307.0Semi standard non polar33892256
L-Kynurenine,3TMS,isomer #5C[Si](C)(C)NC1=CC=CC=C1C(=O)C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C2318.0Standard non polar33892256
L-Kynurenine,3TMS,isomer #5C[Si](C)(C)NC1=CC=CC=C1C(=O)C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C2707.2Standard polar33892256
L-Kynurenine,4TMS,isomer #1C[Si](C)(C)N[C@@H](CC(=O)C1=CC=CC=C1N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C2189.6Semi standard non polar33892256
L-Kynurenine,4TMS,isomer #1C[Si](C)(C)N[C@@H](CC(=O)C1=CC=CC=C1N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C2286.1Standard non polar33892256
L-Kynurenine,4TMS,isomer #1C[Si](C)(C)N[C@@H](CC(=O)C1=CC=CC=C1N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C2395.1Standard polar33892256
L-Kynurenine,4TMS,isomer #2C[Si](C)(C)NC1=CC=CC=C1C(=O)C[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2377.8Semi standard non polar33892256
L-Kynurenine,4TMS,isomer #2C[Si](C)(C)NC1=CC=CC=C1C(=O)C[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2312.8Standard non polar33892256
L-Kynurenine,4TMS,isomer #2C[Si](C)(C)NC1=CC=CC=C1C(=O)C[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2514.6Standard polar33892256
L-Kynurenine,4TMS,isomer #3C[Si](C)(C)N(C1=CC=CC=C1C(=O)C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2332.8Semi standard non polar33892256
L-Kynurenine,4TMS,isomer #3C[Si](C)(C)N(C1=CC=CC=C1C(=O)C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2423.3Standard non polar33892256
L-Kynurenine,4TMS,isomer #3C[Si](C)(C)N(C1=CC=CC=C1C(=O)C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2507.8Standard polar33892256
L-Kynurenine,5TMS,isomer #1C[Si](C)(C)OC(=O)[C@H](CC(=O)C1=CC=CC=C1N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2408.2Semi standard non polar33892256
L-Kynurenine,5TMS,isomer #1C[Si](C)(C)OC(=O)[C@H](CC(=O)C1=CC=CC=C1N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2406.6Standard non polar33892256
L-Kynurenine,5TMS,isomer #1C[Si](C)(C)OC(=O)[C@H](CC(=O)C1=CC=CC=C1N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2335.5Standard polar33892256
L-Kynurenine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CC(=O)C1=CC=CC=C1N2334.7Semi standard non polar33892256
L-Kynurenine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N[C@@H](CC(=O)C1=CC=CC=C1N)C(=O)O2350.9Semi standard non polar33892256
L-Kynurenine,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)NC1=CC=CC=C1C(=O)C[C@H](N)C(=O)O2406.2Semi standard non polar33892256
L-Kynurenine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N[C@@H](CC(=O)C1=CC=CC=C1N)C(=O)O[Si](C)(C)C(C)(C)C2574.2Semi standard non polar33892256
L-Kynurenine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N[C@@H](CC(=O)C1=CC=CC=C1N)C(=O)O[Si](C)(C)C(C)(C)C2586.3Standard non polar33892256
L-Kynurenine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N[C@@H](CC(=O)C1=CC=CC=C1N)C(=O)O[Si](C)(C)C(C)(C)C3063.7Standard polar33892256
L-Kynurenine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC1=CC=CC=C1C(=O)C[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C2599.4Semi standard non polar33892256
L-Kynurenine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC1=CC=CC=C1C(=O)C[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C2659.4Standard non polar33892256
L-Kynurenine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC1=CC=CC=C1C(=O)C[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C3001.3Standard polar33892256
L-Kynurenine,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)NC1=CC=CC=C1C(=O)C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O2651.6Semi standard non polar33892256
L-Kynurenine,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)NC1=CC=CC=C1C(=O)C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O2645.1Standard non polar33892256
L-Kynurenine,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)NC1=CC=CC=C1C(=O)C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O2993.1Standard polar33892256
L-Kynurenine,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)N([C@@H](CC(=O)C1=CC=CC=C1N)C(=O)O)[Si](C)(C)C(C)(C)C2703.7Semi standard non polar33892256
L-Kynurenine,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)N([C@@H](CC(=O)C1=CC=CC=C1N)C(=O)O)[Si](C)(C)C(C)(C)C2684.5Standard non polar33892256
L-Kynurenine,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)N([C@@H](CC(=O)C1=CC=CC=C1N)C(=O)O)[Si](C)(C)C(C)(C)C3130.1Standard polar33892256
L-Kynurenine,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)N(C1=CC=CC=C1C(=O)C[C@H](N)C(=O)O)[Si](C)(C)C(C)(C)C2613.2Semi standard non polar33892256
L-Kynurenine,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)N(C1=CC=CC=C1C(=O)C[C@H](N)C(=O)O)[Si](C)(C)C(C)(C)C2665.1Standard non polar33892256
L-Kynurenine,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)N(C1=CC=CC=C1C(=O)C[C@H](N)C(=O)O)[Si](C)(C)C(C)(C)C3142.6Standard polar33892256
L-Kynurenine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC=CC=C1C(=O)C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2840.4Semi standard non polar33892256
L-Kynurenine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC=CC=C1C(=O)C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2826.9Standard non polar33892256
L-Kynurenine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC=CC=C1C(=O)C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2896.3Standard polar33892256
L-Kynurenine,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC(=O)C1=CC=CC=C1N)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2913.4Semi standard non polar33892256
L-Kynurenine,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC(=O)C1=CC=CC=C1N)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2889.5Standard non polar33892256
L-Kynurenine,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC(=O)C1=CC=CC=C1N)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3042.5Standard polar33892256
L-Kynurenine,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CC(=O)C1=CC=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2774.4Semi standard non polar33892256
L-Kynurenine,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CC(=O)C1=CC=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2879.0Standard non polar33892256
L-Kynurenine,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CC(=O)C1=CC=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2919.4Standard polar33892256
L-Kynurenine,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)N[C@@H](CC(=O)C1=CC=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O2831.6Semi standard non polar33892256
L-Kynurenine,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)N[C@@H](CC(=O)C1=CC=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O2875.4Standard non polar33892256
L-Kynurenine,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)N[C@@H](CC(=O)C1=CC=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O2916.0Standard polar33892256
L-Kynurenine,3TBDMS,isomer #5CC(C)(C)[Si](C)(C)NC1=CC=CC=C1C(=O)C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3000.2Semi standard non polar33892256
L-Kynurenine,3TBDMS,isomer #5CC(C)(C)[Si](C)(C)NC1=CC=CC=C1C(=O)C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2899.7Standard non polar33892256
L-Kynurenine,3TBDMS,isomer #5CC(C)(C)[Si](C)(C)NC1=CC=CC=C1C(=O)C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2960.0Standard polar33892256
L-Kynurenine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)N[C@@H](CC(=O)C1=CC=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C3011.5Semi standard non polar33892256
L-Kynurenine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)N[C@@H](CC(=O)C1=CC=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C3022.1Standard non polar33892256
L-Kynurenine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)N[C@@H](CC(=O)C1=CC=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2816.4Standard polar33892256
L-Kynurenine,4TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC1=CC=CC=C1C(=O)C[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3208.3Semi standard non polar33892256
L-Kynurenine,4TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC1=CC=CC=C1C(=O)C[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3061.9Standard non polar33892256
L-Kynurenine,4TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC1=CC=CC=C1C(=O)C[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2902.5Standard polar33892256
L-Kynurenine,4TBDMS,isomer #3CC(C)(C)[Si](C)(C)N(C1=CC=CC=C1C(=O)C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3215.5Semi standard non polar33892256
L-Kynurenine,4TBDMS,isomer #3CC(C)(C)[Si](C)(C)N(C1=CC=CC=C1C(=O)C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3119.2Standard non polar33892256
L-Kynurenine,4TBDMS,isomer #3CC(C)(C)[Si](C)(C)N(C1=CC=CC=C1C(=O)C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2846.8Standard polar33892256
L-Kynurenine,5TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC(=O)C1=CC=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3431.7Semi standard non polar33892256
L-Kynurenine,5TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC(=O)C1=CC=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3265.5Standard non polar33892256
L-Kynurenine,5TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC(=O)C1=CC=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2816.2Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Kynurenine GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-014l-0931000000-29fa7c323b035cb399d32014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Kynurenine GC-EI-TOF (Non-derivatized)splash10-014l-0931000000-29fa7c323b035cb399d32017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Kynurenine GC-EI-TOF (Non-derivatized)splash10-014l-0931000000-a43ae0acafac266101c42017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Kynurenine GC-EI-TOF (Non-derivatized)splash10-0006-1910000000-fdc25d09b4da4b1d76572017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kynurenine GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dl-9500000000-d7bf6a26c74e0dcabf402016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kynurenine GC-MS (1 TMS) - 70eV, Positivesplash10-00di-4920000000-cb575b96b16b3ef9130f2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kynurenine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kynurenine GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kynurenine GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kynurenine GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kynurenine GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kynurenine GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Kynurenine Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-0006-2910000000-366ce08b5736d68dfad02012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Kynurenine Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-01bd-5900000000-c18e10be7e029474cf032012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Kynurenine Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-00kf-9300000000-0f8238d38819f6f30d122012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Kynurenine LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive-QTOFsplash10-0a4i-0790000000-3fa45266412288bf1c622012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Kynurenine LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive-QTOFsplash10-0007-3900000000-a66f45aff81960af75752012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Kynurenine LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive-QTOFsplash10-00xv-5900000000-15442ec5aaef005401ae2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Kynurenine LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive-QTOFsplash10-00r7-7900000000-0833fe9d2739d329f1972012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Kynurenine LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive-QTOFsplash10-0006-9400000000-d5d45364462a730de4362012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Kynurenine LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOFsplash10-0006-0900000000-13929f0bde71b6326d3f2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Kynurenine LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOFsplash10-0f6w-2900000000-b2d4f361ffee9fd93bb72012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Kynurenine LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOFsplash10-004j-0900000000-96930a886f7bbcc44df32012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Kynurenine LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOFsplash10-000i-0900000000-2441a358973abdb063da2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Kynurenine LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOFsplash10-0udi-0900000000-dc4fee4751d6295751572012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Kynurenine Linear Ion Trap , negative-QTOFsplash10-0006-0900000000-4ec06cc06a3eab2625d62017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Kynurenine Linear Ion Trap , negative-QTOFsplash10-0006-0900000000-319acefac99779fa75522017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Kynurenine Linear Ion Trap , negative-QTOFsplash10-0059-0890000000-4280b92b875a6f754a912017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Kynurenine Linear Ion Trap , negative-QTOFsplash10-0059-0890000000-664e2c8904363418682e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Kynurenine Linear Ion Trap , negative-QTOFsplash10-00dj-0139000000-aa6188977ba2f460f5bc2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Kynurenine Linear Ion Trap , negative-QTOFsplash10-00dj-0139000000-ee71a364df13bd095feb2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Kynurenine 10V, Positive-QTOFsplash10-06r7-0920000000-f2e6efdd3988d3010e332016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Kynurenine 20V, Positive-QTOFsplash10-022a-3900000000-e1c06099462847ad5b972016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Kynurenine 40V, Positive-QTOFsplash10-00di-9700000000-a9df2d5ca325f97f69f12016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Kynurenine 10V, Negative-QTOFsplash10-0a4i-2490000000-9604ae0cc9d437acd8782016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Kynurenine 20V, Negative-QTOFsplash10-00dl-9520000000-8f0ea7d174290496860d2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Kynurenine 40V, Negative-QTOFsplash10-006x-9400000000-9721076505654380d2de2016-09-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Urine
Tissue Locations
  • Brain
  • Epidermis
  • Fibroblasts
  • Intestine
  • Liver
  • Neuron
  • Placenta
  • Spleen
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified1.6 +/- 0.1 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified1.4 (0.7-3.0) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified5.89 (4.89-7.05) uMNewborn (0-30 days old)Not Available
Normal
details
BloodDetected and Quantified2.4 +/- 0.5 uMAdult (>18 years old)MaleNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified1.74 +/- 0.121 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified4.13 (3.44-4.91) uMInfant (0-1 year old)Not Available
Normal
details
BloodDetected and Quantified2.21 +/- 0.57 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified2.61(2.02-3.16) uMChildren (1-13 uears old)Both
Normal
details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected and Quantified1.1-3.2 uMAdult (>18 years old)Both
Normal
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0019 +/- 0.00021 umol/mmol creatinineAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.052 +/- 0.0031 uMAdult (>18 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.054 +/- 0.007 uMAdult (>18 years old)Not SpecifiedNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)Not SpecifiedNormal details
UrineDetected and Quantified0.7503 +/- 0.3831 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Analysis of 30 no...
details
UrineDetected and Quantified0.41 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified2.85 +/- 1.94 umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
    • West Cadwell, N.J...
    • Basel, Switzerlan...
details
UrineDetected and Quantified0.02-0.71 umol/mmol creatinineNewborn (0-30 days old)BothNormal details
UrineDetected and Quantified0.13(0.02-0.68) umol/mmol creatinineNewborn (0-30 days old)FemaleNormal details
UrineDetected and Quantified0.10(0.02-0.71) umol/mmol creatinineNewborn (0-30 days old)MaleNormal details
UrineDetected and Quantified1.345 (0.864-1.825) umol/mmol creatinineChildren (1-13 years old)Not SpecifiedNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.63-1.6 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified0.18 (0.08-0.70) umol/mmol creatinineNewborn (0-30 days old)Both
Normal
    • Analysis of 40 NI...
details
UrineDetected and Quantified1.7 (1.1-2.5) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.41 (0.08-1.31) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.71-0.95 umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified0.56 +/- 0.91 umol/mmol creatinineInfant (0-1 year old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified12.5(3.5-27) uMAdult (>18 years old)BothSepsis details
BloodDetected and Quantified2.35 +/- 0.162 uMAdult (>18 years old)Both
Schizophrenia
details
BloodDetected and Quantified2.82(2.09-3.58) uMChildren (1-13 uears old)Both
Environmental enteric dysfunction
details
BloodDetected and Quantified1.6 uMInfant (0-1 year old)FemaleNicotinamide Adenine Dinucleotide Deficiency details
Cerebrospinal Fluid (CSF)Detected and Quantified0.18 +/- 0.040 uMAdult (>18 years old)Not SpecifiedHydrocephalus details
Cerebrospinal Fluid (CSF)Detected and Quantified0.25 +/- 0.12 uMAdult (>18 years old)Not SpecifiedIntraventricular hemorrhage details
Cerebrospinal Fluid (CSF)Detected and Quantified1.6 +/- 0.58 uMAdult (>18 years old)Not SpecifiedCNS Tumors details
Cerebrospinal Fluid (CSF)Detected and Quantified2.6 +/- 1.06 uMAdult (>18 years old)Not SpecifiedCNS Infections details
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)BothCrohns disease details
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)BothUlcerative colitis details
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)Not SpecifiedCrohns disease details
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)Not SpecifiedUlcerative colitis details
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)Not SpecifiedUnclassified IBD details
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothEnthesitis-related arthritis details
UrineDetected and Quantified0.7154 +/- 0.8277 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Analysis of 30 no...
details
UrineDetected and Quantified0.6012 +/- 0.6597 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Gastroesophageal reflux disease
    • Analysis of 30 no...
details
UrineDetected and Quantified0.256-0.800 umol/mmol creatinineChildren (1-13 years old)FemaleTryptophanuria with dwarfism details
Associated Disorders and Diseases
Disease References
Schizophrenia
  1. 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 ]
Nicotinamide Adenine Dinucleotide Deficiency
  1. 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
  1. 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 ]
Hydrocephalus
  1. Heyes MP, Saito K, Milstien S, Schiff SJ: Quinolinic acid in tumors, hemorrhage and bacterial infections of the central nervous system in children. J Neurol Sci. 1995 Nov;133(1-2):112-8. [PubMed:8583213 ]
Intraventricular hemorrhage
  1. Heyes MP, Saito K, Milstien S, Schiff SJ: Quinolinic acid in tumors, hemorrhage and bacterial infections of the central nervous system in children. J Neurol Sci. 1995 Nov;133(1-2):112-8. [PubMed:8583213 ]
CNS tumors
  1. Heyes MP, Saito K, Milstien S, Schiff SJ: Quinolinic acid in tumors, hemorrhage and bacterial infections of the central nervous system in children. J Neurol Sci. 1995 Nov;133(1-2):112-8. [PubMed:8583213 ]
CNS infections
  1. Heyes MP, Saito K, Milstien S, Schiff SJ: Quinolinic acid in tumors, hemorrhage and bacterial infections of the central nervous system in children. J Neurol Sci. 1995 Nov;133(1-2):112-8. [PubMed:8583213 ]
Crohn's disease
  1. 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 ]
Ulcerative colitis
  1. 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 ]
Eosinophilic esophagitis
  1. Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Tryptophanuria with dwarfism
  1. 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
DrugBank IDDB02070
Phenol Explorer Compound IDNot Available
FooDB IDFDB022181
KNApSAcK IDC00007604
Chemspider ID141580
KEGG Compound IDC00328
BioCyc IDCPD-14736
BiGG ID1445574
Wikipedia LinkKynurenine
METLIN ID72
PubChem Compound161166
PDB IDNot Available
ChEBI ID16946
Food Biomarker OntologyNot Available
VMH IDLKYNR
MarkerDB IDMDB00029988
Good Scents IDNot Available
References
Synthesis ReferenceHayaishi, Osamu. L-Kynurenine sulfate monohydrate. Biochemical Preparations (1953), 3 108-11.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Medana IM, Day NP, Salahifar-Sabet H, Stocker R, Smythe G, Bwanaisa L, Njobvu A, Kayira K, Turner GD, Taylor TE, Hunt NH: Metabolites of the kynurenine pathway of tryptophan metabolism in the cerebrospinal fluid of Malawian children with malaria. J Infect Dis. 2003 Sep 15;188(6):844-9. Epub 2003 Sep 9. [PubMed:12964115 ]
  2. Widner B, Sepp N, Kowald E, Ortner U, Wirleitner B, Fritsch P, Baier-Bitterlich G, Fuchs D: Enhanced tryptophan degradation in systemic lupus erythematosus. Immunobiology. 2000 Apr;201(5):621-30. [PubMed:10834318 ]
  3. Widner B, Sepp N, Kowald E, Kind S, Schmuth M, Fuchs D: Degradation of tryptophan in patients with systemic lupus erythematosus. Adv Exp Med Biol. 1999;467:571-7. [PubMed:10721102 ]
  4. Joseph MH: Determination of kynurenine by a simple gas-liquid chromatographic method applicable to urine, plasma, brain and cerebrospinal fluid. J Chromatogr. 1978 Jul 1;146(1):33-41. [PubMed:670356 ]
  5. Heyes MP, Saito K, Lackner A, Wiley CA, Achim CL, Markey SP: Sources of the neurotoxin quinolinic acid in the brain of HIV-1-infected patients and retrovirus-infected macaques. FASEB J. 1998 Jul;12(10):881-96. [PubMed:9657528 ]
  6. Fujigaki S, Saito K, Takemura M, Fujii H, Wada H, Noma A, Seishima M: Species differences in L-tryptophan-kynurenine pathway metabolism: quantification of anthranilic acid and its related enzymes. Arch Biochem Biophys. 1998 Oct 15;358(2):329-35. [PubMed:9784247 ]
  7. Widner B, Werner ER, Schennach H, Fuchs D: An HPLC method to determine tryptophan and kynurenine in serum simultaneously. Adv Exp Med Biol. 1999;467:827-32. [PubMed:10721136 ]
  8. Saito K, Fujigaki S, Heyes MP, Shibata K, Takemura M, Fujii H, Wada H, Noma A, Seishima M: Mechanism of increases in L-kynurenine and quinolinic acid in renal insufficiency. Am J Physiol Renal Physiol. 2000 Sep;279(3):F565-72. [PubMed:10966936 ]
  9. Heyes MP, Saito K, Milstien S, Schiff SJ: Quinolinic acid in tumors, hemorrhage and bacterial infections of the central nervous system in children. J Neurol Sci. 1995 Nov;133(1-2):112-8. [PubMed:8583213 ]
  10. Martinsons A, Rudzite V, Groma V, Bratslavska O, Widner B, Fuchs D: Kynurenine and neopterin in chronic glomerulonephritis. Adv Exp Med Biol. 1999;467:579-86. [PubMed:10721103 ]
  11. 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 ]
  12. Moroni F, Carpenedo R, Chiarugi A: Kynurenine hydroxylase and kynureninase inhibitors as tools to study the role of kynurenine metabolites in the central nervous system. Adv Exp Med Biol. 1996;398:203-10. [PubMed:8906267 ]
  13. Calandra P: Research on tryptophan metabolites "via kynurenine" in epidermis of man and mouse. Acta Vitaminol Enzymol. 1975;29(1-6):158-60. [PubMed:1244085 ]
  14. Manuelpillai U, Nicholls T, Wallace EM, Phillips DJ, Guillemin G, Walker D: Increased mRNA expression of kynurenine pathway enzymes in human placentae exposed to bacterial endotoxin. Adv Exp Med Biol. 2003;527:85-9. [PubMed:15206719 ]
  15. Greengard O: Relationship between urinary excretion of kynurenine and liver tryptophan oxygenase activity. Am J Clin Nutr. 1971 Jun;24(6):709-11. [PubMed:5581008 ]
  16. Heinmets F: Computer simulation and analysis of tryptophan metabolism via kynurenine pathway in liver. Comput Biol Med. 1974 Sep;1(4):323-36. [PubMed:4600391 ]
  17. Okuno E, Nakamura M, Schwarcz R: Two kynurenine aminotransferases in human brain. Brain Res. 1991 Mar 1;542(2):307-12. [PubMed:2029638 ]
  18. Altman K, Greengard O: Correlation of kynurenine excretion with liver tryptophan pyrrolase levels in disease and after hydrocortisone induction. J Clin Invest. 1966 Oct;45(10):1527-34. [PubMed:5925511 ]
  19. Pearson SJ, Meldrum A, Reynolds GP: An investigation of the activities of 3-hydroxykynureninase and kynurenine aminotransferase in the brain in Huntington's disease. J Neural Transm Gen Sect. 1995;102(1):67-73. [PubMed:8785025 ]
  20. Hartai Z, Klivenyi P, Janaky T, Penke B, Dux L, Vecsei L: Kynurenine metabolism in plasma and in red blood cells in Parkinson's disease. J Neurol Sci. 2005 Dec 15;239(1):31-5. Epub 2005 Aug 15. [PubMed:16099471 ]
  21. Pawlak D, Pawlak K, Malyszko J, Mysliwiec M, Buczko W: Accumulation of toxic products degradation of kynurenine in hemodialyzed patients. Int Urol Nephrol. 2001;33(2):399-404. [PubMed:12092667 ]
  22. 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 ]
  23. 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 ]
  24. 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 ]
  25. 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 ]
  26. Wang Y, Liu H, McKenzie G, Witting PK, Stasch JP, Hahn M, Changsirivathanathamrong D, Wu BJ, Ball HJ, Thomas SR, Kapoor V, Celermajer DS, Mellor AL, Keaney JF Jr, Hunt NH, Stocker R: Kynurenine is an endothelium-derived relaxing factor produced during inflammation. Nat Med. 2010 Mar;16(3):279-85. doi: 10.1038/nm.2092. Epub 2010 Feb 28. [PubMed:20190767 ]
  27. Nguyen NT, Kimura A, Nakahama T, Chinen I, Masuda K, Nohara K, Fujii-Kuriyama Y, Kishimoto T: Aryl hydrocarbon receptor negatively regulates dendritic cell immunogenicity via a kynurenine-dependent mechanism. Proc Natl Acad Sci U S A. 2010 Nov 16;107(46):19961-6. doi: 10.1073/pnas.1014465107. Epub 2010 Nov 1. [PubMed:21041655 ]
  28. Bartoli F, Misiak B, Callovini T, Cavaleri D, Cioni RM, Crocamo C, Savitz JB, Carra G: The kynurenine pathway in bipolar disorder: a meta-analysis on the peripheral blood levels of tryptophan and related metabolites. Mol Psychiatry. 2021 Jul;26(7):3419-3429. doi: 10.1038/s41380-020-00913-1. Epub 2020 Oct 19. [PubMed:33077852 ]
  29. Wonodi I, Stine OC, Sathyasaikumar KV, Roberts RC, Mitchell BD, Hong LE, Kajii Y, Thaker GK, Schwarcz R: Downregulated kynurenine 3-monooxygenase gene expression and enzyme activity in schizophrenia and genetic association with schizophrenia endophenotypes. Arch Gen Psychiatry. 2011 Jul;68(7):665-74. doi: 10.1001/archgenpsychiatry.2011.71. [PubMed:21727251 ]
  30. Guillemin GJ, Brew BJ, Noonan CE, Takikawa O, Cullen KM: Indoleamine 2,3 dioxygenase and quinolinic acid immunoreactivity in Alzheimer's disease hippocampus. Neuropathol Appl Neurobiol. 2005 Aug;31(4):395-404. doi: 10.1111/j.1365-2990.2005.00655.x. [PubMed:16008823 ]
  31. Wirleitner B, Rudzite V, Neurauter G, Murr C, Kalnins U, Erglis A, Trusinskis K, Fuchs D: Immune activation and degradation of tryptophan in coronary heart disease. Eur J Clin Invest. 2003 Jul;33(7):550-4. doi: 10.1046/j.1365-2362.2003.01186.x. [PubMed:12814390 ]
  32. Gulaj E, Pawlak K, Bien B, Pawlak D: Kynurenine and its metabolites in Alzheimer's disease patients. Adv Med Sci. 2010;55(2):204-11. doi: 10.2478/v10039-010-0023-6. [PubMed:20639188 ]

Enzymes

General function:
Involved in transferase activity, transferring nitrogenous groups
Specific function:
Catalyzes the irreversible transamination of the L-tryptophan metabolite L-kynurenine to form kynurenic acid (KA). Plays a key role in amino acid metabolism. Important for metabolite exchange between mitochondria and cytosol. Facilitates cellular uptake of long-chain free fatty acids.
Gene Name:
GOT2
Uniprot ID:
P00505
Molecular weight:
47517.285
Reactions
Kynurenine + Oxoglutaric acid → 4-(2-Aminophenyl)-2,4-dioxobutanoic acid + Glutamic aciddetails
General function:
Involved in metabolic process
Specific function:
Catalyzes the cleavage of L-kynurenine (L-Kyn) and L-3-hydroxykynurenine (L-3OHKyn) into anthranilic acid (AA) and 3-hydroxyanthranilic acid (3-OHAA), respectively. Has a preference for the L-3-hydroxy form. Also has cysteine-conjugate-beta-lyase activity.
Gene Name:
KYNU
Uniprot ID:
Q16719
Molecular weight:
34634.47
Reactions
Kynurenine + Water → 2-Aminobenzoic acid + L-Alaninedetails
General function:
Involved in transferase activity, transferring nitrogenous groups
Specific function:
Transaminase with broad substrate specificity. Has transaminase activity towards aminoadipate, kynurenine, methionine and glutamate. Shows activity also towards tryptophan, aspartate and hydroxykynurenine. Accepts a variety of oxo-acids as amino-group acceptors, with a preference for 2-oxoglutarate, 2-oxocaproic acid, phenylpyruvate and alpha-oxo-gamma-methiol butyric acid. Can also use glyoxylate as amino-group acceptor (in vitro).
Gene Name:
AADAT
Uniprot ID:
Q8N5Z0
Molecular weight:
47351.17
Reactions
Kynurenine + Oxoglutaric acid → 4-(2-Aminophenyl)-2,4-dioxobutanoic acid + Glutamic aciddetails
General function:
Involved in 1-aminocyclopropane-1-carboxylate synthase activity
Specific function:
Catalyzes the irreversible transamination of the L-tryptophan metabolite L-kynurenine to form kynurenic acid (KA). Metabolizes the cysteine conjugates of certain halogenated alkenes and alkanes to form reactive metabolites. Catalyzes the beta-elimination of S-conjugates and Se-conjugates of L-(seleno)cysteine, resulting in the cleavage of the C-S or C-Se bond.
Gene Name:
CCBL1
Uniprot ID:
Q16773
Molecular weight:
47874.765
Reactions
Kynurenine + Oxoglutaric acid → 4-(2-Aminophenyl)-2,4-dioxobutanoic acid + Glutamic aciddetails
General function:
Involved in transcription regulator activity
Specific function:
Ligand-activated transcriptional activator. Binds to the XRE promoter region of genes it activates. Activates the expression of multiple phase I and II xenobiotic chemical metabolizing enzyme genes (such as the CYP1A1 gene). Mediates biochemical and toxic effects of halogenated aromatic hydrocarbons. Involved in cell-cycle regulation. Likely to play an important role in the development and maturation of many tissues
Gene Name:
AHR
Uniprot ID:
P35869
Molecular weight:
96146.7
General function:
Involved in monooxygenase activity
Specific function:
Catalyzes the hydroxylation of L-kynurenine (L-Kyn) to form 3-hydroxy-L-kynurenine (L-3OHKyn). Required for synthesis of quinolinic acid, a neurotoxic NMDA receptor antagonist and potential endogenous inhibitor of NMDA receptor signaling in axonal targeting, synaptogenesis and apoptosis during brain development. Quinolinic acid may also affect NMDA receptor signaling in pancreatic beta cells, osteoblasts, myocardial cells, and the gastrointestinal tract.
Gene Name:
KMO
Uniprot ID:
O15229
Molecular weight:
55809.445
Reactions
Kynurenine + NADPH + Oxygen → L-3-Hydroxykynurenine + NADP + Waterdetails
Kynurenine + Oxygen + NADPH + Hydrogen Ion → L-3-Hydroxykynurenine + NADP + Waterdetails
General function:
Transcription
Specific function:
Not Available
Gene Name:
AADAT
Uniprot ID:
Q4W5N8
Molecular weight:
47351.2
General function:
Involved in hydrolase activity
Specific function:
Catalyzes the hydrolysis of N-formyl-L-kynurenine to L-kynurenine, the second step in the kynurenine pathway of tryptophan degradation. Kynurenine may be further oxidized to nicotinic acid, NAD(H) and NADP(H). Required for elimination of toxic metabolites (By similarity).
Gene Name:
AFMID
Uniprot ID:
Q63HM1
Molecular weight:
33991.5
Reactions
L-Formylkynurenine + Water → Formic acid + Kynureninedetails
General function:
Involved in transferase activity, transferring nitrogenous groups
Specific function:
Catalyzes the irreversible transamination of the L-tryptophan metabolite L-kynurenine to form kynurenic acid (KA). May catalyze the beta-elimination of S-conjugates and Se-conjugates of L-(seleno)cysteine, resulting in the cleavage of the C-S or C-Se bond (By similarity). Has transaminase activity towards L-kynurenine, tryptophan, phenylalanine, serine, cysteine, methionine, histidine, glutamine and asparagine with glyoxylate as an amino group acceptor (in vitro). Has lower activity with 2-oxoglutarate as amino group acceptor (in vitro) (By similarity).
Gene Name:
CCBL2
Uniprot ID:
Q6YP21
Molecular weight:
51399.855
Reactions
Kynurenine + Oxoglutaric acid → 4-(2-Aminophenyl)-2,4-dioxobutanoic acid + Glutamic aciddetails
Kynurenine + Glyoxylic acid → 4-(2-Aminophenyl)-2,4-dioxobutanoic acid + Glycinedetails