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Showing NP-Card for 5-Hydroxytryptophol (NP0000901)

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Record Information
Version2.0
Created at2006-02-21 08:10:09 UTC
Updated at2020-11-24 22:19:14 UTC
NP-MRD IDNP0000901
Secondary Accession NumbersNone
Natural Product Identification
Common Name5-Hydroxytryptophol
Description5-Hydroxytryptophol is a relatively minor metabolite of serotonin that is excreted primarily as the glucuronide conjugate in human urine. 5-Hydroxytryptophol becomes more important quantitatively during alcohol intoxication, when a shift in the metabolism of serotonin occurs from 5-hydroxyindole acetic acid toward increased (15-fold higher) formation of 5-hydroxytryptophol due to the inhibition of aldehyde dehydrogenase by ethanol-derived acetaldehyde. Urinary excretion of 5-hydroxytryptophol has also been shown to be markedly increased for several hours following intake of foods rich in serotonin, such as bananas. Wide interspecies variation has been reported in the metabolism serotonin to 5-hydroxytryptophol; 5-Hydroxytryptophol makes up 35% of the excreted serotonin metabolites in the rat on average and 10 to 20% in several other species. Human UDP-glucuronosyltransferase 1A6 (UGT1A6) plays a predominant role in the glucuronidation of 5-hydroxytryptophol by human liver microsomes. (PMID 15258112 ).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000901 (5-Hydroxytryptophol)


  Mrv1652305271900002D          

 13 14  0  0  0  0            999 V2000
   13.3305  -10.3384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3378   -9.5110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0537   -9.1061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7653   -9.5236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7594  -10.3486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0421  -10.7560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5517   -9.2742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0318   -9.9450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5423  -10.6090    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.6233   -9.0984    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8121   -8.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2644   -7.8744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5248   -7.0917    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
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9  5  1  0  0  0  0
  2 10  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
M  END
Download

3D MOL for NP0000901 (5-Hydroxytryptophol)

HMDB0001855
     RDKit          3D
5-Hydroxytryptophol
 24 25  0  0  0  0  0  0  0  0999 V2000
    4.3117    0.0388    0.4054 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1236    0.8159    0.2739 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0280   -0.1003   -0.1663 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7264    0.5603   -0.3255 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4277    1.8480   -0.6896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9301    2.0050   -0.6756 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5021    0.8547   -0.3150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8286    0.4828   -0.1618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1702   -0.8120    0.2180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1603   -1.7169    0.4401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4503   -3.0188    0.8189 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8315   -1.3246    0.2822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4969   -0.0432   -0.0945 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1183   -0.6937    1.0783 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9481    1.4149    1.1559 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3455    1.5020   -0.6057 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9130   -0.8895    0.6388 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3120   -0.6930   -1.0625 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0795    2.6595   -0.9590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4895    2.8533   -0.8980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6388    1.1786   -0.3259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2064   -1.1242    0.3375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5921   -3.7730    0.1776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0370   -2.0246    0.4529 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
 10 12  1  0
 12 13  2  0
 13  4  1  0
 13  7  1  0
  1 14  1  0
  2 15  1  0
  2 16  1  0
  3 17  1  0
  3 18  1  0
  5 19  1  0
  6 20  1  0
  8 21  1  0
  9 22  1  0
 11 23  1  0
 12 24  1  0
M  END
Download

3D SDF for NP0000901 (5-Hydroxytryptophol)


  Mrv1652305271900002D          

 13 14  0  0  0  0            999 V2000
   13.3305  -10.3384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3378   -9.5110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0537   -9.1061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7653   -9.5236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7594  -10.3486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0421  -10.7560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5517   -9.2742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0318   -9.9450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5423  -10.6090    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.6233   -9.0984    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8121   -8.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2644   -7.8744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5248   -7.0917    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
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9  5  1  0  0  0  0
  2 10  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000901

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCCC1=CNC2=CC=C(O)C=C12

> <INCHI_IDENTIFIER>
InChI=1S/C10H11NO2/c12-4-3-7-6-11-10-2-1-8(13)5-9(7)10/h1-2,5-6,11-13H,3-4H2

> <INCHI_KEY>
KQROHCSYOGBQGJ-UHFFFAOYSA-N

> <FORMULA>
C10H11NO2

> <MOLECULAR_WEIGHT>
177.1998

> <EXACT_MASS>
177.078978601

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
18.85673974074358

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(2-hydroxyethyl)-1H-indol-5-ol

> <ALOGPS_LOGP>
0.91

> <JCHEM_LOGP>
1.2897539250000003

> <ALOGPS_LOGS>
-1.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.891538341234408

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.556124438991318

> <JCHEM_PKA_STRONGEST_BASIC>
-2.427895964995842

> <JCHEM_POLAR_SURFACE_AREA>
56.25

> <JCHEM_REFRACTIVITY>
50.6963

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.18e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
hydroxytryptophol

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000901 (5-Hydroxytryptophol)

HMDB0001855
     RDKit          3D
5-Hydroxytryptophol
 24 25  0  0  0  0  0  0  0  0999 V2000
    4.3117    0.0388    0.4054 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1236    0.8159    0.2739 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0280   -0.1003   -0.1663 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7264    0.5603   -0.3255 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4277    1.8480   -0.6896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9301    2.0050   -0.6756 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5021    0.8547   -0.3150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8286    0.4828   -0.1618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1702   -0.8120    0.2180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1603   -1.7169    0.4401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4503   -3.0188    0.8189 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8315   -1.3246    0.2822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4969   -0.0432   -0.0945 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1183   -0.6937    1.0783 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9481    1.4149    1.1559 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3455    1.5020   -0.6057 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9130   -0.8895    0.6388 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3120   -0.6930   -1.0625 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0795    2.6595   -0.9590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4895    2.8533   -0.8980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6388    1.1786   -0.3259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2064   -1.1242    0.3375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5921   -3.7730    0.1776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0370   -2.0246    0.4529 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
 10 12  1  0
 12 13  2  0
 13  4  1  0
 13  7  1  0
  1 14  1  0
  2 15  1  0
  2 16  1  0
  3 17  1  0
  3 18  1  0
  5 19  1  0
  6 20  1  0
  8 21  1  0
  9 22  1  0
 11 23  1  0
 12 24  1  0
M  END
Download

PDB for NP0000901 (5-Hydroxytryptophol)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0      24.884 -19.298   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      24.897 -17.754   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      26.234 -16.998   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      27.562 -17.777   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      27.551 -19.317   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      26.212 -20.078   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      29.030 -17.312   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      29.926 -18.564   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      29.012 -19.803   0.000  0.00  0.00           N+0
HETATM   10  O   UNK     0      23.563 -16.984   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      29.516 -15.851   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      28.494 -14.699   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      28.980 -13.238   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6    9                                                  
CONECT    6    5    1                                                       
CONECT    7    4    8   11                                                  
CONECT    8    7    9                                                       
CONECT    9    8    5                                                       
CONECT   10    2                                                            
CONECT   11    7   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END
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3D PDB for NP0000901 (5-Hydroxytryptophol)

COMPND    HMDB0001855
HETATM    1  O1  UNL     1       4.312   0.039   0.405  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.124   0.816   0.274  1.00  0.00           C  
HETATM    3  C2  UNL     1       2.028  -0.100  -0.166  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.726   0.560  -0.325  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.428   1.848  -0.690  1.00  0.00           C  
HETATM    6  N1  UNL     1      -0.930   2.005  -0.676  1.00  0.00           N  
HETATM    7  C5  UNL     1      -1.502   0.855  -0.315  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.829   0.483  -0.162  1.00  0.00           C  
HETATM    9  C7  UNL     1      -3.170  -0.812   0.218  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.160  -1.717   0.440  1.00  0.00           C  
HETATM   11  O2  UNL     1      -2.450  -3.019   0.819  1.00  0.00           O  
HETATM   12  C9  UNL     1      -0.831  -1.325   0.282  1.00  0.00           C  
HETATM   13  C10 UNL     1      -0.497  -0.043  -0.095  1.00  0.00           C  
HETATM   14  H1  UNL     1       4.118  -0.694   1.078  1.00  0.00           H  
HETATM   15  H2  UNL     1       2.948   1.415   1.156  1.00  0.00           H  
HETATM   16  H3  UNL     1       3.346   1.502  -0.606  1.00  0.00           H  
HETATM   17  H4  UNL     1       1.913  -0.890   0.639  1.00  0.00           H  
HETATM   18  H5  UNL     1       2.312  -0.693  -1.062  1.00  0.00           H  
HETATM   19  H6  UNL     1       1.079   2.659  -0.959  1.00  0.00           H  
HETATM   20  H7  UNL     1      -1.490   2.853  -0.898  1.00  0.00           H  
HETATM   21  H8  UNL     1      -3.639   1.179  -0.326  1.00  0.00           H  
HETATM   22  H9  UNL     1      -4.206  -1.124   0.338  1.00  0.00           H  
HETATM   23  H10 UNL     1      -2.592  -3.773   0.178  1.00  0.00           H  
HETATM   24  H11 UNL     1      -0.037  -2.025   0.453  1.00  0.00           H  
CONECT    1    2   14
CONECT    2    3   15   16
CONECT    3    4   17   18
CONECT    4    5    5   13
CONECT    5    6   19
CONECT    6    7   20
CONECT    7    8    8   13
CONECT    8    9   21
CONECT    9   10   10   22
CONECT   10   11   12
CONECT   11   23
CONECT   12   13   13   24
END
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SMILES for NP0000901 (5-Hydroxytryptophol)

OCCC1=CNC2=CC=C(O)C=C12
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INCHI for NP0000901 (5-Hydroxytryptophol)

InChI=1S/C10H11NO2/c12-4-3-7-6-11-10-2-1-8(13)5-9(7)10/h1-2,5-6,11-13H,3-4H2
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View in JSmol
Synonyms
ValueSource
5-HTOLHMDB
5-Hydroxy-1H-indole-3-ethanolHMDB
5-Hydroxy-1H-indole-3-ethanol(9ci)HMDB
5-Hydroxy-3-indoleHMDB
5-Hydroxy-3-indoleacetic acidHMDB
5-Hydroxy-indole-acetic acidHMDB
5-Hydroxyindoacetic acidHMDB
5-HydroxyindolHMDB
5-HydroxyindolacetateHMDB
5-Hydroxyindolacetic acidHMDB
5-Hydroxyindole-3-ethanolHMDB
5-Hydroxyindole-acetic acidHMDB
Hydroxyindoleacetic acidHMDB
HydroxytryptopholHMDB
Chemical FormulaC10H11NO2
Average Mass177.1998 Da
Monoisotopic Mass177.07898 Da
IUPAC Name3-(2-hydroxyethyl)-1H-indol-5-ol
Traditional Namehydroxytryptophol
CAS Registry Number154-02-9
SMILES
OCCC1=CNC2=CC=C(O)C=C12
InChI Identifier
InChI=1S/C10H11NO2/c12-4-3-7-6-11-10-2-1-8(13)5-9(7)10/h1-2,5-6,11-13H,3-4H2
InChI KeyKQROHCSYOGBQGJ-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
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Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroxyindoles. These are organic compounds containing an indole moiety that carries a hydroxyl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassHydroxyindoles
Direct ParentHydroxyindoles
Alternative Parents
Substituents
  • 3-alkylindole
  • Hydroxyindole
  • Indole
  • 1-hydroxy-2-unsubstituted benzenoid
  • Substituted pyrrole
  • Benzenoid
  • Heteroaromatic compound
  • Pyrrole
  • Azacycle
  • Organic oxygen compound
  • Alcohol
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.18 g/LALOGPS
logP0.91ALOGPS
logP1.29ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)9.56ChemAxon
pKa (Strongest Basic)-2.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area56.25 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity50.7 m³·mol⁻¹ChemAxon
Polarizability18.86 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0001855
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022711
KNApSAcK IDC00045185
Chemspider ID8708
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5730
PubChem Compound9061
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Curtius HC, Wolfensberger M, Redweik U, Leimbacher W, Maibach RA, Isler W: Mass fragmentography of 5-hydroxytryptophol and 5-methoxytryptophol in human cerebrospinal fluid. J Chromatogr. 1975 Oct 29;112:523-31. [PubMed:1184685 ]
  2. Krishnaswamy S, Hao Q, Von Moltke LL, Greenblatt DJ, Court MH: Evaluation of 5-hydroxytryptophol and other endogenous serotonin (5-hydroxytryptamine) analogs as substrates for UDP-glucuronosyltransferase 1A6. Drug Metab Dispos. 2004 Aug;32(8):862-9. [PubMed:15258112 ]