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Showing metabocard for Tryptophol (HMDB0003447)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2006-08-12 21:10:36 UTC
Update Date2023-02-21 17:16:40 UTC
HMDB IDHMDB0003447
Secondary Accession Numbers
  • HMDB03447
Metabolite Identification
Common NameTryptophol
DescriptionTryptophol, also known as indole-3-ethanol, is an indolyl alcohol that is ethanol substituted by a 1H-indol-3-yl group at position 2. It has a role as a Saccharomyces cerevisiae metabolite, an auxin and a plant metabolite. Tryptophol is a catabolite of tryptophan converted by the gut microbiota. After absorption through the intestinal epithelium, tryptophan catabolites enter the bloodstream and are later excreted in the urine (PMID:30120222 ). Tryptophol production was negatively associated with interferon-gamma production (IFNγ) which suggests that tryptophol has anti-inflammatory properties (PMID:27814509 ). Tryptophol has also been identified as the hypnotic agent in trypanosomal sleeping sickness, and because it is formed in vivo after ethanol or disulfiram treatment, it is also associated with the study of alcoholism (PMID:7241135 ).
Structure
Data?1676999800
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0003447 (Tryptophol)


  Mrv1652301282018322D          

 12 13  0  0  0  0            999 V2000
 9997.0764 9999.4249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.8215 9998.6402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.3735 9998.0272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1805 9998.1986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.295810000.3109    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8834 9999.5964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.4354 9998.9833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.1891 9999.3189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.102810000.1393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.9036 9998.9064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.6180 9999.3189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.3324 9998.9064    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  5  6  1  0  0  0  0
  5  9  1  0  0  0  0
  8 10  1  0  0  0  0
  4  7  1  0  0  0  0
  6  1  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
M  END
Download

3D MOL for HMDB0003447 (Tryptophol)

HMDB0003447
     RDKit          3D
Tryptophol
 23 24  0  0  0  0  0  0  0  0999 V2000
    2.0146   -0.5409    1.7271 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6939    0.0921    0.7084 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0418   -0.0746   -0.6507 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6720    0.4631   -0.6859 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3067    1.6950   -1.1958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0201    1.8464   -1.0336 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4997    0.7401   -0.4348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7594    0.3479   -0.0355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9814   -0.8745    0.5675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9554   -1.7631    0.7995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6884   -1.3777    0.4023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4577   -0.1537   -0.2018 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6190   -0.5843    2.5119 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7641    1.1741    0.9452 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7194   -0.3382    0.6573 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6860    0.3388   -1.4526 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0474   -1.1908   -0.8383 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9389    2.4507   -1.6580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5611    2.7025   -1.3368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5778    1.0440   -0.2141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9810   -1.1821    0.8827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1380   -2.7324    1.2772 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1163   -2.0825    0.5794 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  4  1  0
 12  7  1  0
  1 13  1  0
  2 14  1  0
  2 15  1  0
  3 16  1  0
  3 17  1  0
  5 18  1  0
  6 19  1  0
  8 20  1  0
  9 21  1  0
 10 22  1  0
 11 23  1  0
M  END
Download

3D SDF for HMDB0003447 (Tryptophol)


  Mrv1652301282018322D          

 12 13  0  0  0  0            999 V2000
 9997.0764 9999.4249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.8215 9998.6402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.3735 9998.0272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1805 9998.1986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.295810000.3109    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8834 9999.5964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.4354 9998.9833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.1891 9999.3189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.102810000.1393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.9036 9998.9064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.6180 9999.3189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.3324 9998.9064    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  5  6  1  0  0  0  0
  5  9  1  0  0  0  0
  8 10  1  0  0  0  0
  4  7  1  0  0  0  0
  6  1  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0003447

> <DATABASE_NAME>
hmdb

> <SMILES>
OCCC1=CNC2=C1C=CC=C2

> <INCHI_IDENTIFIER>
InChI=1S/C10H11NO/c12-6-5-8-7-11-10-4-2-1-3-9(8)10/h1-4,7,11-12H,5-6H2

> <INCHI_KEY>
MBBOMCVGYCRMEA-UHFFFAOYSA-N

> <FORMULA>
C10H11NO

> <MOLECULAR_WEIGHT>
161.2004

> <EXACT_MASS>
161.084063979

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
17.87526502062822

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(1H-indol-3-yl)ethan-1-ol

> <ALOGPS_LOGP>
1.82

> <JCHEM_LOGP>
1.5933192466666666

> <ALOGPS_LOGS>
-2.00

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.392512752772014

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.796075232386734

> <JCHEM_PKA_STRONGEST_BASIC>
-2.4393148808629768

> <JCHEM_POLAR_SURFACE_AREA>
36.019999999999996

> <JCHEM_REFRACTIVITY>
48.71540000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.61e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tryptophol

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0003447 (Tryptophol)

HMDB0003447
     RDKit          3D
Tryptophol
 23 24  0  0  0  0  0  0  0  0999 V2000
    2.0146   -0.5409    1.7271 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6939    0.0921    0.7084 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0418   -0.0746   -0.6507 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6720    0.4631   -0.6859 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3067    1.6950   -1.1958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0201    1.8464   -1.0336 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4997    0.7401   -0.4348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7594    0.3479   -0.0355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9814   -0.8745    0.5675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9554   -1.7631    0.7995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6884   -1.3777    0.4023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4577   -0.1537   -0.2018 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6190   -0.5843    2.5119 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7641    1.1741    0.9452 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7194   -0.3382    0.6573 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6860    0.3388   -1.4526 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0474   -1.1908   -0.8383 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9389    2.4507   -1.6580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5611    2.7025   -1.3368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5778    1.0440   -0.2141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9810   -1.1821    0.8827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1380   -2.7324    1.2772 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1163   -2.0825    0.5794 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  4  1  0
 12  7  1  0
  1 13  1  0
  2 14  1  0
  2 15  1  0
  3 16  1  0
  3 17  1  0
  5 18  1  0
  6 19  1  0
  8 20  1  0
  9 21  1  0
 10 22  1  0
 11 23  1  0
M  END
Download

PDB for HMDB0003447 (Tryptophol)

HEADER    PROTEIN                                 28-JAN-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-JAN-20         0                                  
HETATM    1  C   UNK     0    8661.2098665.593   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8660.7338664.128   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8661.7648662.984   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8663.2708663.304   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0    8663.4858667.247   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0    8662.7168665.913   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8663.7468664.769   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8665.1538665.395   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8664.9928666.927   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8666.4878664.625   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8667.8208665.395   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0    8669.1548664.625   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    7                                                       
CONECT    5    6    9                                                       
CONECT    6    7    5    1                                                  
CONECT    7    6    8    4                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8    5                                                       
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END
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3D PDB for HMDB0003447 (Tryptophol)

COMPND    HMDB0003447
HETATM    1  O1  UNL     1       2.015  -0.541   1.727  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.694   0.092   0.708  1.00  0.00           C  
HETATM    3  C2  UNL     1       2.042  -0.075  -0.651  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.672   0.463  -0.686  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.307   1.695  -1.196  1.00  0.00           C  
HETATM    6  N1  UNL     1      -1.020   1.846  -1.034  1.00  0.00           N  
HETATM    7  C5  UNL     1      -1.500   0.740  -0.435  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.759   0.348  -0.035  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.981  -0.874   0.567  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.955  -1.763   0.800  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.688  -1.378   0.402  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.458  -0.154  -0.202  1.00  0.00           C  
HETATM   13  H1  UNL     1       2.619  -0.584   2.512  1.00  0.00           H  
HETATM   14  H2  UNL     1       2.764   1.174   0.945  1.00  0.00           H  
HETATM   15  H3  UNL     1       3.719  -0.338   0.657  1.00  0.00           H  
HETATM   16  H4  UNL     1       2.686   0.339  -1.453  1.00  0.00           H  
HETATM   17  H5  UNL     1       2.047  -1.191  -0.838  1.00  0.00           H  
HETATM   18  H6  UNL     1       0.939   2.451  -1.658  1.00  0.00           H  
HETATM   19  H7  UNL     1      -1.561   2.703  -1.337  1.00  0.00           H  
HETATM   20  H8  UNL     1      -3.578   1.044  -0.214  1.00  0.00           H  
HETATM   21  H9  UNL     1      -3.981  -1.182   0.883  1.00  0.00           H  
HETATM   22  H10 UNL     1      -2.138  -2.732   1.277  1.00  0.00           H  
HETATM   23  H11 UNL     1       0.116  -2.083   0.579  1.00  0.00           H  
CONECT    1    2   13
CONECT    2    3   14   15
CONECT    3    4   16   17
CONECT    4    5    5   12
CONECT    5    6   18
CONECT    6    7   19
CONECT    7    8    8   12
CONECT    8    9   20
CONECT    9   10   10   21
CONECT   10   11   22
CONECT   11   12   12   23
END
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SMILES for HMDB0003447 (Tryptophol)

OCCC1=CNC2=C1C=CC=C2
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INCHI for HMDB0003447 (Tryptophol)

InChI=1S/C10H11NO/c12-6-5-8-7-11-10-4-2-1-3-9(8)10/h1-4,7,11-12H,5-6H2
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View in JSmolView Stereo Labels
Synonyms
ValueSource
1H-Indole-3-ethanolChEBI
1H-Indolyl-3-ethanolChEBI
2-(indol-3-yl)EthanolChEBI
3-(2-Hydroxyethyl)indoleChEBI
Indole-3-ethanolChEBI
TryptophanolChEBI
2-(1H-indol-3-yl)EthanolHMDB
2-(3-Indolyl)ethanolHMDB
2-(3-IndolylethanolHMDB
3-(b-Hydroxyethyl)indoleHMDB
3-(beta-Hydroxyethyl)indoleHMDB
3-IndoleethanolHMDB
3-IndolylethanolHMDB
b-(3-Indole)ethanolHMDB
beta-(3-Indole)ethanolHMDB
beta-indol-3-YlethanolHMDB
DL-TryptophanolHMDB
IEAHMDB
Indole ethanolHMDB
IndoleethanolHMDB
TryptopholHMDB, KEGG
3-(2-Hydroxyethyl)-1H-indoleHMDB
3-(β-Hydroxyethyl)indoleHMDB
3-Indole ethanolHMDB
β-(3-Indole)ethanolHMDB
Chemical FormulaC10H11NO
Average Molecular Weight161.2004
Monoisotopic Molecular Weight161.084063979
IUPAC Name2-(1H-indol-3-yl)ethan-1-ol
Traditional Nametryptophol
CAS Registry Number526-55-6
SMILES
OCCC1=CNC2=C1C=CC=C2
InChI Identifier
InChI=1S/C10H11NO/c12-6-5-8-7-11-10-4-2-1-3-9(8)10/h1-4,7,11-12H,5-6H2
InChI KeyMBBOMCVGYCRMEA-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndoles
Direct Parent3-alkylindoles
Alternative Parents
Substituents
  • 3-alkylindole
  • Benzenoid
  • Substituted pyrrole
  • Heteroaromatic compound
  • Pyrrole
  • Azacycle
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point59 °CNot Available
Boiling Point357.80 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility2749 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.280 (est)The Good Scents Company Information System
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Not Available133.4http://allccs.zhulab.cn/database/detail?ID=AllCCS00002126
[M+H]+Not Available133.9http://allccs.zhulab.cn/database/detail?ID=AllCCS00002126
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.61 g/LALOGPS
logP1.82ALOGPS
logP1.59ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)15.8ChemAxon
pKa (Strongest Basic)-2.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area36.02 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity48.72 m³·mol⁻¹ChemAxon
Polarizability17.88 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+134.22931661259
DarkChem[M-H]-132.25531661259
DeepCCS[M+H]+134.15130932474
DeepCCS[M-H]-130.3530932474
DeepCCS[M-2H]-167.98830932474
DeepCCS[M+Na]+143.28730932474
AllCCS[M+H]+134.932859911
AllCCS[M+H-H2O]+130.332859911
AllCCS[M+NH4]+139.132859911
AllCCS[M+Na]+140.332859911
AllCCS[M-H]-136.032859911
AllCCS[M+Na-2H]-136.632859911
AllCCS[M+HCOO]-137.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
TryptopholOCCC1=CNC2=C1C=CC=C22907.9Standard polar33892256
TryptopholOCCC1=CNC2=C1C=CC=C21719.2Standard non polar33892256
TryptopholOCCC1=CNC2=C1C=CC=C21769.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Tryptophol,1TMS,isomer #1C[Si](C)(C)OCCC1=C[NH]C2=CC=CC=C121821.7Semi standard non polar33892256
Tryptophol,1TMS,isomer #2C[Si](C)(C)N1C=C(CCO)C2=CC=CC=C211813.1Semi standard non polar33892256
Tryptophol,2TMS,isomer #1C[Si](C)(C)OCCC1=CN([Si](C)(C)C)C2=CC=CC=C121871.2Semi standard non polar33892256
Tryptophol,2TMS,isomer #1C[Si](C)(C)OCCC1=CN([Si](C)(C)C)C2=CC=CC=C121883.2Standard non polar33892256
Tryptophol,2TMS,isomer #1C[Si](C)(C)OCCC1=CN([Si](C)(C)C)C2=CC=CC=C121990.9Standard polar33892256
Tryptophol,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCCC1=C[NH]C2=CC=CC=C122078.0Semi standard non polar33892256
Tryptophol,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C=C(CCO)C2=CC=CC=C212070.5Semi standard non polar33892256
Tryptophol,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C122320.4Semi standard non polar33892256
Tryptophol,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C122302.9Standard non polar33892256
Tryptophol,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C122239.4Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Tryptophol GC-MS (2 TMS)splash10-0udi-1591000000-5b173cc0ac0dc2b874a92014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Tryptophol GC-MS (Non-derivatized)splash10-0udi-1591000000-5b173cc0ac0dc2b874a92017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Tryptophol GC-EI-TOF (Non-derivatized)splash10-0udi-0490000000-15708d306e1f75b1e76f2017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tryptophol GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-0900000000-d2769447ff27a79be3672016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tryptophol GC-MS (1 TMS) - 70eV, Positivesplash10-00yi-5690000000-765b6a566d2067c199b02017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tryptophol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-001i-2900000000-20fec68981d54c2e70022015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Tryptophol LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOFsplash10-03di-0900000000-593c6fbb6f64e16e7f052012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tryptophol LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOFsplash10-03e9-0900000000-54f7b6548b8a00c91c3f2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tryptophol LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOFsplash10-003u-0900000000-fb2793cd76eefaaf45c52012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tryptophol LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOFsplash10-016r-0900000000-a97ae0f4c1633b83c4152012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tryptophol LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOFsplash10-014i-0900000000-d00c24bc728f46156c602012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tryptophol LC-ESI-QQ , negative-QTOFsplash10-03di-0900000000-593c6fbb6f64e16e7f052017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tryptophol LC-ESI-QQ , negative-QTOFsplash10-03e9-0900000000-54f7b6548b8a00c91c3f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tryptophol LC-ESI-QQ , negative-QTOFsplash10-003u-0900000000-fb2793cd76eefaaf45c52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tryptophol LC-ESI-QQ , negative-QTOFsplash10-016r-0900000000-78c3b34c10c43b6a93172017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tryptophol LC-ESI-QQ , negative-QTOFsplash10-014i-0900000000-d00c24bc728f46156c602017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tryptophol , negative-QTOFsplash10-03di-0900000000-d41cd8e81a55b3e005382017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tryptophol 35V, Negative-QTOFsplash10-03di-0900000000-aeba8d28d8681fb1473d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tryptophol 10V, Negative-QTOFsplash10-03di-0900000000-b46601ffc736985fcdf82021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tryptophol 40V, Negative-QTOFsplash10-014i-2900000000-3e7e36fd8027ab6c9e962021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tryptophol 20V, Negative-QTOFsplash10-003u-0900000000-2ba4c5a87b74cfd62e022021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tryptophol Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-01ox-0900000000-5fb5f5b5efe809cbe9ad2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tryptophol Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-00kf-0900000000-44158c348db109504af42012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tryptophol Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-014l-6900000000-48b709f034a27e74e73f2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tryptophol 20V, Positive-QTOFsplash10-0006-0900000000-5927d4ac720f209af38d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tryptophol 40V, Positive-QTOFsplash10-00kf-5900000000-4bc97e2ed06c230bbbde2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tryptophol 10V, Positive-QTOFsplash10-0006-0900000000-4807fdc919bf8c468f722021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tryptophol 20V, Positive-QTOFsplash10-0006-0900000000-63222dc5b6f22cd7cc132021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tryptophol 40V, Positive-QTOFsplash10-00kf-9800000000-314e270d78e7a9ec16a92021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tryptophol 10V, Positive-QTOFsplash10-0006-0900000000-3f8e0d1410267c0ad66e2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tryptophol 10V, Negative-QTOFsplash10-03di-0900000000-bfeeeabc14ffd14b537e2015-05-27Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)2012-12-05Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, 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 LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB010973
KNApSAcK IDC00000114
Chemspider ID10235
KEGG Compound IDC00955
BioCyc IDCPD-341
BiGG IDNot Available
Wikipedia LinkTryptophol
METLIN ID6932
PubChem Compound10685
PDB IDNot Available
ChEBI ID17890
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1295861
References
Synthesis ReferenceSnyder, H. R.; Pilgrim, Frederick J. Preparation of 3-indoleacetic acid; new synthesis of tryptophol. Journal of the American Chemical Society (1948), 70 3770-1.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Cornford EM, Crane PD, Braun LD, Bocash WD, Nyerges AM, Oldendorf WH: Reduction in brain glucose utilization rate after tryptophol (3-indole ethanol) treatment. J Neurochem. 1981 May;36(5):1758-65. [PubMed:7241135 ]
  2. Roager HM, Licht TR: Microbial tryptophan catabolites in health and disease. Nat Commun. 2018 Aug 17;9(1):3294. doi: 10.1038/s41467-018-05470-4. [PubMed:30120222 ]
  3. Schirmer M, Smeekens SP, Vlamakis H, Jaeger M, Oosting M, Franzosa EA, Ter Horst R, Jansen T, Jacobs L, Bonder MJ, Kurilshikov A, Fu J, Joosten LAB, Zhernakova A, Huttenhower C, Wijmenga C, Netea MG, Xavier RJ: Linking the Human Gut Microbiome to Inflammatory Cytokine Production Capacity. Cell. 2016 Nov 3;167(4):1125-1136.e8. doi: 10.1016/j.cell.2016.10.020. [PubMed:27814509 ]