Showing metabocard for Tryptophol (MMDBc0007020)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-05-15 00:21:44 UTC
Update Date2024-10-15 22:10:28 UTC
Metabolite IDMMDBc0007020
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
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f922c5af508>


  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 #<Metabolite:0x00007f922c5af508>

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 #<Metabolite:0x00007f922c5af508>


  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>
MMDBc0007020

> <DATABASE_NAME>
MIME

> <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 #<Metabolite:0x00007f922c5af508>

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 #<Metabolite:0x00007f922c5af508>

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
Download

3D PDB for #<Metabolite:0x00007f922c5af508>

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
Download

SMILES for #<Metabolite:0x00007f922c5af508>

OCCC1=CNC2=C1C=CC=C2
Download

INCHI for #<Metabolite:0x00007f922c5af508>

InChI=1S/C10H11NO/c12-6-5-8-7-11-10-4-2-1-3-9(8)10/h1-4,7,11-12H,5-6H2
Download
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
Molecular FormulaC10H11NO
Average Mass161.2004
Monoisotopic Mass161.084063979
IUPAC Name2-(1H-indol-3-yl)ethan-1-ol
Traditional Nametryptophol
CAS Registry NumberNot Available
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