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Showing metabocard for 5-Hydroxyindoleacetic acid (HMDB0000763)

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enzymes (8) Show 8 proteins
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-05-30 20:56:03 UTC
HMDB IDHMDB0000763
Secondary Accession Numbers
  • HMDB00763
Metabolite Identification
Common Name5-Hydroxyindoleacetic acid
Description5-Hydroxyindoleacetic acid, also known as 5-hydroxyindole-3-acetate or 5-HIAA, belongs to the class of organic compounds known as indole-3-acetic acid derivatives. Indole-3-acetic acid derivatives are compounds containing an acetic acid (or a derivative) linked to the C3 carbon atom of an indole. 5-Hydroxyindoleacetic acid exists in all living organisms, ranging from bacteria to humans. In humans, 5-hydroxyindoleacetic acid is a breakdown product of serotonin that is excreted in the urine and it also participates in a number of enzymatic reactions. 5-hydroxyindoleacetic acid can be biosynthesized from 5-hydroxyindoleacetaldehyde; which is catalyzed by the mitochondrial enzyme aldehyde dehydrogenase. In addition, 5-hydroxyindoleacetic acid and S-adenosylmethionine can be converted into 5-methoxyindoleacetate and S-adenosylhomocysteine through its interaction with the enzyme acetylserotonin O-methyltransferase. 5-Hydroxyindoleacetic acid is also involved in the metabolism of tryptophan. 5-Hydroxyindoleacetic acid has been found to be associated with several human diseases such as brunner syndrome, friedreich's ataxia, schizophrenia, and olivopontocerebral atrophy; 5-hydroxyindoleacetic acid has also been linked to the inborn metabolic disorder sepiapterin reductase deficiency. Elevated levels of 5-hydroxyindoleacetic acid in urine (>20 uM) are indicative of appendicitis and gastroenteritis (PMID: 11462886 ). Serotonin and 5-Hydroxyindoleacetic acid are produced in excess amounts by carcinoid tumors, and levels of these substances may be measured in the urine to test for carcinoid tumors (NCI). 5-Hydroxyindoleacetic acid has also been found to be a product of human gut microbiota.
Structure
Data?1676999709
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000763 (5-Hydroxyindoleacetic acid)


  Mrv1652302032018292D          

 14 15  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
10000.618010000.1439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1185 9997.2425    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
 11 13  2  0  0  0  0
  3 14  1  0  0  0  0
M  END
Download

3D MOL for HMDB0000763 (5-Hydroxyindoleacetic acid)

HMDB0000763
     RDKit          3D
5-Hydroxyindoleacetic acid
 23 24  0  0  0  0  0  0  0  0999 V2000
   -2.0462    0.4140   -1.6745 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6793    0.7166   -0.6363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7937    1.5231   -0.7717 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1870    0.1877    0.6580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9708   -0.6456    0.4777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9490   -2.0219    0.5232 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3322   -2.4104    0.3147 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1271   -1.3402    0.1386 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4929   -1.1624   -0.1043 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0417    0.0925   -0.2441 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2304    1.2030   -0.1431 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7344    2.4929   -0.2764 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8745    1.0277    0.0982 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3169   -0.2236    0.2393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0261    2.1453   -0.0254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9685    1.0872    1.2969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0067   -0.3876    1.1453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7820   -2.6964    0.6925 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6849   -3.3949    0.2887 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1112   -2.0395   -0.1799 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1150    0.2329   -0.4349 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1103    3.2787   -0.1962 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2378    1.9210    0.1765 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14  5  1  0
 14  8  1  0
  3 15  1  0
  4 16  1  0
  4 17  1  0
  6 18  1  0
  7 19  1  0
  9 20  1  0
 10 21  1  0
 12 22  1  0
 13 23  1  0
M  END
Download

3D SDF for HMDB0000763 (5-Hydroxyindoleacetic acid)


  Mrv1652302032018292D          

 14 15  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
10000.618010000.1439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1185 9997.2425    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
 11 13  2  0  0  0  0
  3 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000763

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)CC1=CNC2=C1C=C(O)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C10H9NO3/c12-7-1-2-9-8(4-7)6(5-11-9)3-10(13)14/h1-2,4-5,11-12H,3H2,(H,13,14)

> <INCHI_KEY>
DUUGKQCEGZLZNO-UHFFFAOYSA-N

> <FORMULA>
C10H9NO3

> <MOLECULAR_WEIGHT>
191.1834

> <EXACT_MASS>
191.058243159

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
18.70645401922691

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(5-hydroxy-1H-indol-3-yl)acetic acid

> <ALOGPS_LOGP>
1.28

> <JCHEM_LOGP>
1.4061907766666666

> <ALOGPS_LOGS>
-2.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.558275552338404

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.215990424188327

> <JCHEM_PKA_STRONGEST_BASIC>
-5.50801830576937

> <JCHEM_POLAR_SURFACE_AREA>
73.32

> <JCHEM_REFRACTIVITY>
50.433

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.80e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
hydroxyindoleacetic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0000763 (5-Hydroxyindoleacetic acid)

HMDB0000763
     RDKit          3D
5-Hydroxyindoleacetic acid
 23 24  0  0  0  0  0  0  0  0999 V2000
   -2.0462    0.4140   -1.6745 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6793    0.7166   -0.6363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7937    1.5231   -0.7717 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1870    0.1877    0.6580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9708   -0.6456    0.4777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9490   -2.0219    0.5232 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3322   -2.4104    0.3147 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1271   -1.3402    0.1386 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4929   -1.1624   -0.1043 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0417    0.0925   -0.2441 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2304    1.2030   -0.1431 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7344    2.4929   -0.2764 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8745    1.0277    0.0982 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3169   -0.2236    0.2393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0261    2.1453   -0.0254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9685    1.0872    1.2969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0067   -0.3876    1.1453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7820   -2.6964    0.6925 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6849   -3.3949    0.2887 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1112   -2.0395   -0.1799 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1150    0.2329   -0.4349 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1103    3.2787   -0.1962 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2378    1.9210    0.1765 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14  5  1  0
 14  8  1  0
  3 15  1  0
  4 16  1  0
  4 17  1  0
  6 18  1  0
  7 19  1  0
  9 20  1  0
 10 21  1  0
 12 22  1  0
 13 23  1  0
M  END
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PDB for HMDB0000763 (5-Hydroxyindoleacetic acid)

HEADER    PROTEIN                                 03-FEB-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-FEB-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
HETATM   13  O   UNK     0    8667.8208666.935   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0    8661.2888661.519   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   14                                                  
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   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    3                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END
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3D PDB for HMDB0000763 (5-Hydroxyindoleacetic acid)

COMPND    HMDB0000763
HETATM    1  O1  UNL     1      -2.046   0.414  -1.675  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.679   0.717  -0.636  1.00  0.00           C  
HETATM    3  O2  UNL     1      -3.794   1.523  -0.772  1.00  0.00           O  
HETATM    4  C2  UNL     1      -2.187   0.188   0.658  1.00  0.00           C  
HETATM    5  C3  UNL     1      -0.971  -0.646   0.478  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.949  -2.022   0.523  1.00  0.00           C  
HETATM    7  N1  UNL     1       0.332  -2.410   0.315  1.00  0.00           N  
HETATM    8  C5  UNL     1       1.127  -1.340   0.139  1.00  0.00           C  
HETATM    9  C6  UNL     1       2.493  -1.162  -0.104  1.00  0.00           C  
HETATM   10  C7  UNL     1       3.042   0.092  -0.244  1.00  0.00           C  
HETATM   11  C8  UNL     1       2.230   1.203  -0.143  1.00  0.00           C  
HETATM   12  O3  UNL     1       2.734   2.493  -0.276  1.00  0.00           O  
HETATM   13  C9  UNL     1       0.874   1.028   0.098  1.00  0.00           C  
HETATM   14  C10 UNL     1       0.317  -0.224   0.239  1.00  0.00           C  
HETATM   15  H1  UNL     1      -4.026   2.145  -0.025  1.00  0.00           H  
HETATM   16  H2  UNL     1      -1.969   1.087   1.297  1.00  0.00           H  
HETATM   17  H3  UNL     1      -3.007  -0.388   1.145  1.00  0.00           H  
HETATM   18  H4  UNL     1      -1.782  -2.696   0.692  1.00  0.00           H  
HETATM   19  H5  UNL     1       0.685  -3.395   0.289  1.00  0.00           H  
HETATM   20  H6  UNL     1       3.111  -2.039  -0.180  1.00  0.00           H  
HETATM   21  H7  UNL     1       4.115   0.233  -0.435  1.00  0.00           H  
HETATM   22  H8  UNL     1       2.110   3.279  -0.196  1.00  0.00           H  
HETATM   23  H9  UNL     1       0.238   1.921   0.176  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   15
CONECT    4    5   16   17
CONECT    5    6    6   14
CONECT    6    7   18
CONECT    7    8   19
CONECT    8    9    9   14
CONECT    9   10   20
CONECT   10   11   11   21
CONECT   11   12   13
CONECT   12   22
CONECT   13   14   14   23
END
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SMILES for HMDB0000763 (5-Hydroxyindoleacetic acid)

OC(=O)CC1=CNC2=C1C=C(O)C=C2
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INCHI for HMDB0000763 (5-Hydroxyindoleacetic acid)

InChI=1S/C10H9NO3/c12-7-1-2-9-8(4-7)6(5-11-9)3-10(13)14/h1-2,4-5,11-12H,3H2,(H,13,14)
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View in JSmolView Stereo Labels
Synonyms
ValueSource
5-HIAAChEBI
5-Hydroxy-1H-indole-3-acetic acidChEBI
5-Hydroxyindol-3-ylacetic acidChEBI
5-Hydroxyindole-3-acetic acidChEBI
5-Hydroxy-1H-indole-3-acetateGenerator
5-Hydroxyindol-3-ylacetateGenerator
5-Hydroxyindole-3-acetateGenerator
5-HydroxyindoleacetateGenerator
5-Hydroxy-3-indolylacetateHMDB
5-Hydroxy-iaaHMDB
5-Hydroxy-indole-3-acetateHMDB
5-Hydroxy-indole-3-acetic acidHMDB
5-HydroxyheteroauxinHMDB
5-Hydroxyindole acetateHMDB
5-OxyindoleacetateHMDB
5-Oxyindoleacetic acidHMDB
5HIAAHMDB
HydroxyindoleacetateHMDB
5-Hydroxyindolamine acetic acidMeSH, HMDB
Hydroxyindoleacetic acidMeSH, HMDB
5 Hydroxy 3 indoleacetic acidMeSH, HMDB
5 Hydroxyindolamine acetic acidMeSH, HMDB
5-Hydroxy-3-indoleacetic acidMeSH, HMDB
Acetic acid, 5-hydroxyindolamineMeSH, HMDB
Acid, hydroxyindoleaceticMeSH, HMDB
Acid, 5-hydroxy-3-indoleaceticMeSH, HMDB
Acid, 5-hydroxyindolamine aceticMeSH, HMDB
Chemical FormulaC10H9NO3
Average Molecular Weight191.1834
Monoisotopic Molecular Weight191.058243159
IUPAC Name2-(5-hydroxy-1H-indol-3-yl)acetic acid
Traditional Namehydroxyindoleacetic acid
CAS Registry Number54-16-0
SMILES
OC(=O)CC1=CNC2=C1C=C(O)C=C2
InChI Identifier
InChI=1S/C10H9NO3/c12-7-1-2-9-8(4-7)6(5-11-9)3-10(13)14/h1-2,4-5,11-12H,3H2,(H,13,14)
InChI KeyDUUGKQCEGZLZNO-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as indole-3-acetic acid derivatives. Indole-3-acetic acid derivatives are compounds containing an acetic acid (or a derivative) linked to the C3 carbon atom of an indole.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndolyl carboxylic acids and derivatives
Direct ParentIndole-3-acetic acid derivatives
Alternative Parents
Substituents
  • Indole-3-acetic acid derivative
  • 3-alkylindole
  • Hydroxyindole
  • Indole
  • 1-hydroxy-2-unsubstituted benzenoid
  • Substituted pyrrole
  • Benzenoid
  • Pyrrole
  • Heteroaromatic compound
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxide
  • Organic nitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect
Health effect
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Biological roleIndustrial application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point161 - 163 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility24 mg/mLNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Not Available137.3http://allccs.zhulab.cn/database/detail?ID=AllCCS00000467
[M+H]+Not Available141.1http://allccs.zhulab.cn/database/detail?ID=AllCCS00000467
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.8 g/LALOGPS
logP1.28ALOGPS
logP1.41ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)4.22ChemAxon
pKa (Strongest Basic)-5.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area73.32 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity50.43 m³·mol⁻¹ChemAxon
Polarizability18.71 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+143.28131661259
DarkChem[M-H]-139.61131661259
AllCCS[M+H]+141.16232859911
AllCCS[M-H]-139.9832859911
DeepCCS[M+H]+138.89530932474
DeepCCS[M-H]-136.31530932474
DeepCCS[M-2H]-171.92430932474
DeepCCS[M+Na]+147.29530932474
AllCCS[M+H]+141.232859911
AllCCS[M+H-H2O]+136.932859911
AllCCS[M+NH4]+145.232859911
AllCCS[M+Na]+146.332859911
AllCCS[M-H]-140.032859911
AllCCS[M+Na-2H]-140.232859911
AllCCS[M+HCOO]-140.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5-Hydroxyindoleacetic acidOC(=O)CC1=CNC2=C1C=C(O)C=C23833.2Standard polar33892256
5-Hydroxyindoleacetic acidOC(=O)CC1=CNC2=C1C=C(O)C=C21931.8Standard non polar33892256
5-Hydroxyindoleacetic acidOC(=O)CC1=CNC2=C1C=C(O)C=C22260.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5-Hydroxyindoleacetic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)CC1=C[NH]C2=CC=C(O)C=C122177.5Semi standard non polar33892256
5-Hydroxyindoleacetic acid,1TMS,isomer #2C[Si](C)(C)OC1=CC=C2[NH]C=C(CC(=O)O)C2=C12215.4Semi standard non polar33892256
5-Hydroxyindoleacetic acid,1TMS,isomer #3C[Si](C)(C)N1C=C(CC(=O)O)C2=CC(O)=CC=C212247.4Semi standard non polar33892256
5-Hydroxyindoleacetic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)CC1=C[NH]C2=CC=C(O[Si](C)(C)C)C=C122171.3Semi standard non polar33892256
5-Hydroxyindoleacetic acid,2TMS,isomer #2C[Si](C)(C)OC(=O)CC1=CN([Si](C)(C)C)C2=CC=C(O)C=C122191.7Semi standard non polar33892256
5-Hydroxyindoleacetic acid,2TMS,isomer #3C[Si](C)(C)OC1=CC=C2C(=C1)C(CC(=O)O)=CN2[Si](C)(C)C2232.0Semi standard non polar33892256
5-Hydroxyindoleacetic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)CC1=CN([Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C122200.6Semi standard non polar33892256
5-Hydroxyindoleacetic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)CC1=CN([Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C122213.5Standard non polar33892256
5-Hydroxyindoleacetic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)CC1=CN([Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C122287.3Standard polar33892256
5-Hydroxyindoleacetic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CC1=C[NH]C2=CC=C(O)C=C122473.5Semi standard non polar33892256
5-Hydroxyindoleacetic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C2[NH]C=C(CC(=O)O)C2=C12499.9Semi standard non polar33892256
5-Hydroxyindoleacetic acid,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)N1C=C(CC(=O)O)C2=CC(O)=CC=C212488.5Semi standard non polar33892256
5-Hydroxyindoleacetic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CC1=C[NH]C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C122701.4Semi standard non polar33892256
5-Hydroxyindoleacetic acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O)C=C122693.6Semi standard non polar33892256
5-Hydroxyindoleacetic acid,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)C(CC(=O)O)=CN2[Si](C)(C)C(C)(C)C2749.5Semi standard non polar33892256
5-Hydroxyindoleacetic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C122886.8Semi standard non polar33892256
5-Hydroxyindoleacetic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C122841.5Standard non polar33892256
5-Hydroxyindoleacetic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C122607.8Standard polar33892256
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Urine
Tissue Locations
  • Brain
  • Liver
  • Neuron
  • Platelet
  • Prostate
  • Spleen
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0516 +/- 0.0068 uMAdult (>18 years old)BothNormal details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.080 +/- 0.023 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.307 (0.152-0.462) uMInfant (0-1 year old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.143 +/- 0.0450 uMNot SpecifiedNot SpecifiedNormal
    • Geigy Scientific ...
 details
Cerebrospinal Fluid (CSF)Detected and Quantified0.428-1.122 uMChildren (1-13 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.119-0.608 uMChildren (1-13 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.07-0.14 uMAdult (>18 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.109-0.214 uMChildren (1-13 years old)MaleNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.1-0.245 uMChildren (1-13 years old)MaleNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.61 +/- 0.06 uMChildren (1-13 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.4 +/- 0.07 uMAdult (>18 years old)MaleNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.47 (0.15-0.80) uMInfant (0-1 year old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.025 +/- 0.011 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.120-0.400 uMChildren (1-13 years old)Female
Normal		 details
Cerebrospinal Fluid (CSF)Detected and Quantified0.143 +/- 0.045 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedBoth
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)Not SpecifiedNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified0.3-5.1 umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified3.0 (0.48-4.5) umol/mmol creatinineChildren (1-13 years old)BothNormal
    • Geigy Scientific ...
    • West Cadwell, N.J...
    • Basel, Switzerlan...
 details
UrineDetected and Quantified1.57 +/- 0.38 umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
    • West Cadwell, N.J...
    • Basel, Switzerlan...
 details
UrineDetected and Quantified4.75 +/- 5.38 umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified1.5-2.0 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified1.18 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified11.0 (4.0-18.0) umol/mmol creatinineInfant (0-1 year old)Not SpecifiedNormal details
UrineDetected and Quantified54.058 +/- 23.536 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Analysis of 30 no...
 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified6.583 +/- 5.31 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Analysis of 30 no...
 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified1.5 (0-7.2) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
UrineDetected and Quantified1.1 +/- 0.5 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified1.4-1.7 umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified<21.85 umol/mmol creatinineChildren (1 - 18 years old)Both
Normal
    • BC Children's Hos...
 details
UrineDetected and Quantified2.4 +/- 0.40 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified2.9 (0.4-5.8) umol/mmol creatinineAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified3.900-17.700 umol/mmol creatinineChildren (1-13 years old)Female
Normal		 details
UrineDetected and Quantified0-0.0314 umol/mmol creatinineAdolescent (13-18 years old)Not SpecifiedNormal details
UrineDetected and Quantified8.69 +/- 0.38 umol/mmol creatinineNewborn (0-30 days old)Both
Normal
    • Analysis of 40 NI...
 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0475 +/- 0.0130 uMAdult (>18 years old)MaleSchizophrenia details
BloodDetected and Quantified0.0449 +/- 0.0140 uMAdult (>18 years old)FemaleSchizophrenia details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Female
Breast cancer		 details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0703 +/- 0.0254 uMAdult (>18 years old)Bothceliac disease details
Cerebrospinal Fluid (CSF)Detected and Quantified0.22725 (0.117-0.519) uMNewborn (0-30 days old)Not SpecifiedPNPO deficiency details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0045 (0.004-0.005) uMChildren (1-13 years old)Malesepiapterin reductase deficiency details
Cerebrospinal Fluid (CSF)Detected and Quantified0.056 +/- 0.022 uMAdult (>18 years old)BothSchizophrenia details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0025 (0.0000-0.0050) uMInfant (0-1 year old)MaleAromatic L-amino acid decarboxylase deficiency details
Cerebrospinal Fluid (CSF)Detected and Quantified0.519 uMNewborn (0-30 days old)Not SpecifiedPNPO deficiency details
Cerebrospinal Fluid (CSF)Detected and Quantified0.122 uMNewborn (0-30 days old)Not SpecifiedPNPO deficiency details
Cerebrospinal Fluid (CSF)Detected and Quantified0.117 uMNewborn (0-30 days old)Not SpecifiedPNPO deficiency details
Cerebrospinal Fluid (CSF)Detected and Quantified0.151 uMNewborn (0-30 days old)Not SpecifiedPNPO deficiency details
Cerebrospinal Fluid (CSF)Detected and Quantified0.071 +/- 0.0268 uMAdult (>18 years old)Not Specifiedceliac disease details
Cerebrospinal Fluid (CSF)Detected and Quantified0.33 +/- 0.04 uMChildren (1-13 years old)BothEpilepsy details
Cerebrospinal Fluid (CSF)Detected and Quantified0.1491 +/- 0.0591 uMAdult (>18 years old)Not SpecifiedLeuprolide acetate-induced hypogonadism details
Cerebrospinal Fluid (CSF)Detected and Quantified0.1373 +/- 0.0457 uMAdult (>18 years old)Not SpecifiedLeuprolide acetate-induced hypogonadism with testosterone replacment details
Cerebrospinal Fluid (CSF)Detected and Quantified0.08 +/- 0.08 uMAdult (>18 years old)Both
Major depression		 details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0887 +/- 0.0385 uMNot SpecifiedNot SpecifiedBipolar with childhood ADHD (attention-deficit hyperactivity disorder) details
Cerebrospinal Fluid (CSF)Detected and Quantified0.116 +/- 0.0479 uMNot SpecifiedNot SpecifiedBipolar disorder details
Cerebrospinal Fluid (CSF)Detected and Quantified0.126 +/- 0.0526 uMNot SpecifiedNot SpecifiedControl (men) details
Cerebrospinal Fluid (CSF)Detected and Quantified0.096 +/- 0.0384 uMNot SpecifiedFemaleControl (women) details
Cerebrospinal Fluid (CSF)Detected and Quantified0.112 +/- 0.0483 uMNot SpecifiedNot Specified
Bipolar disorder		 details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0983 +/- 0.0444 uMNot SpecifiedNot Specified
Bipolar disorder		 details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0912 +/- 0.0387 uMNot SpecifiedNot Specified
Bipolar disorder		 details
Cerebrospinal Fluid (CSF)Detected and Quantified0.123 +/- 0.0505 uMNot SpecifiedNot Specified
Bipolar disorder		 details
Cerebrospinal Fluid (CSF)Detected and Quantified0.116 +/- 0.053 uMNot SpecifiedNot Specified
Bipolar disorder		 details
Cerebrospinal Fluid (CSF)Detected and Quantified0.104 +/- 0.0386 uMNot SpecifiedNot Specified
Bipolar disorder		 details
Cerebrospinal Fluid (CSF)Detected and Quantified0.1 +/- 0.01 uMAdult (>18 years old)BothFriedreich's ataxia details
Cerebrospinal Fluid (CSF)Detected and Quantified0.11 +/- 0.01 uMAdult (>18 years old)BothOlivopontocerebellar atrophy (OPCA) details
Cerebrospinal Fluid (CSF)Detected and Quantified0.1 +/- 0.02 uMAdult (>18 years old)BothAutosomal recessive spastic ataxia of Charlevoix-Saguena details
Cerebrospinal Fluid (CSF)Detected and Quantified0.019 +/- 0.0094 uMAdult (>18 years old)BothSchizophrenia details
Cerebrospinal Fluid (CSF)Detected and Quantified0.027 uMInfant (0-1 year old)Female
Aromatic L-amino acid decarboxylase deficiency		 details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0120-0.0220 uMChildren (1-13 years old)Female
Aromatic L-amino acid decarboxylase deficiency		 details
Cerebrospinal Fluid (CSF)Detected but not QuantifiedNot QuantifiedAdult (>18 years old)Female
Breast cancer		 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 Quantified0.8-1.4 umol/mmol creatinineAdult (>18 years old)MaleBrunner Syndrome details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Metabolic syndrome		 details
UrineDetected and Quantified0.9 +/- 0.0 umol/mmol creatinineInfant (0-1 year old)MaleAromatic L-amino acid decarboxylase deficiency details
UrineDetected and Quantified69.452 +/- 34.984 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Analysis of 30 no...
 details
UrineDetected and Quantified87.711 +/- 36.841 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Gastroesophageal reflux disease
    • Analysis of 30 no...
 details
UrineDetected and Quantified13.570 umol/mmol creatinineAdult (>18 years old)Female
Pregnancy		 details
UrineDetected and Quantified5.004 +/- 1.463 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Analysis of 30 no...
 details
UrineDetected and Quantified5.0 umol/mmol creatinineAdult (>18 years old)MaleCarcinoid tumors details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothBladder cancer details
UrineDetected and Quantified0.0921 umol/mmol creatinineAdolescent (13-18 years old)FemaleDopamine-serotonin Vesicular Transport Defect details
UrineDetected and Quantified0.2 umol/mmol creatinineChildren (1-13 years old)Female
Aromatic L-amino acid decarboxylase deficiency		 details
UrineDetected and Quantified2.2 umol/mmol creatinineInfant (0-1 year old)Female
Aromatic L-amino acid decarboxylase deficiency		 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Female
Breast cancer		 details
Associated Disorders and Diseases
Disease References
Schizophrenia
  1. Alfredsson G, Wiesel FA: Monoamine metabolites and amino acids in serum from schizophrenic patients before and during sulpiride treatment. Psychopharmacology (Berl). 1989;99(3):322-7. [PubMed:2480613 ]
  2. Do KQ, Lauer CJ, Schreiber W, Zollinger M, Gutteck-Amsler U, Cuenod M, Holsboer F: gamma-Glutamylglutamine and taurine concentrations are decreased in the cerebrospinal fluid of drug-naive patients with schizophrenic disorders. J Neurochem. 1995 Dec;65(6):2652-62. [PubMed:7595563 ]
  3. Gattaz WF, Waldmeier P, Beckmann H: CSF monoamine metabolites in schizophrenic patients. Acta Psychiatr Scand. 1982 Nov;66(5):350-60. [PubMed:6184954 ]
Epilepsy
  1. Shaywitz BA, Cohen DJ, Bowers MB: Reduced cerebrospinal fluid 5-hydroxyindoleacetic acid and homovanillic acid in children with epilepsy. Neurology. 1975 Jan;25(1):72-9. [PubMed:803305 ]
Major depressive disorder
  1. Sheline Y, Bardgett ME, Csernansky JG: Correlated reductions in cerebrospinal fluid 5-HIAA and MHPG concentrations after treatment with selective serotonin reuptake inhibitors. J Clin Psychopharmacol. 1997 Feb;17(1):11-4. [PubMed:9004051 ]
Friedreich's ataxia
  1. Botez MI, Young SN: Biogenic amine metabolites and thiamine in cerebrospinal fluid in heredo-degenerative ataxias. Can J Neurol Sci. 2001 May;28(2):134-40. [PubMed:11383938 ]
Olivopontocerebral atrophy
  1. Botez MI, Young SN: Biogenic amine metabolites and thiamine in cerebrospinal fluid in heredo-degenerative ataxias. Can J Neurol Sci. 2001 May;28(2):134-40. [PubMed:11383938 ]
Hereditary spastic paraplegia
  1. Botez MI, Young SN: Biogenic amine metabolites and thiamine in cerebrospinal fluid in heredo-degenerative ataxias. Can J Neurol Sci. 2001 May;28(2):134-40. [PubMed:11383938 ]
Aromatic L-amino acid decarboxylase deficiency
  1. Abdenur JE, Abeling N, Specola N, Jorge L, Schenone AB, van Cruchten AC, Chamoles NA: Aromatic l-aminoacid decarboxylase deficiency: unusual neonatal presentation and additional findings in organic acid analysis. Mol Genet Metab. 2006 Jan;87(1):48-53. Epub 2005 Nov 9. [PubMed:16288991 ]
  2. Abeling NG, van Gennip AH, Barth PG, van Cruchten A, Westra M, Wijburg FA: Aromatic L-amino acid decarboxylase deficiency: a new case with a mild clinical presentation and unexpected laboratory findings. J Inherit Metab Dis. 1998 Jun;21(3):240-2. [PubMed:9686366 ]
Celiac disease
  1. Hallert C, Astrom J, Sedvall G: Psychic disturbances in adult coeliac disease. III. Reduced central monoamine metabolism and signs of depression. Scand J Gastroenterol. 1982 Jan;17(1):25-8. [PubMed:6182605 ]
  2. Hallert C, Allenmark S, Larsson-Cohn U, Sedvall G: High level of pyridoxal 5'-phosphate in the cerebrospinal fluid of adult celiac patients. Am J Clin Nutr. 1982 Nov;36(5):851-4. [PubMed:6182788 ]
Pyridoxamine 5-prime-phosphate oxidase deficiency
  1. Ormazabal A, Oppenheim M, Serrano M, Garcia-Cazorla A, Campistol J, Ribes A, Ruiz A, Moreno J, Hyland K, Clayton P, Heales S, Artuch R: Pyridoxal 5'-phosphate values in cerebrospinal fluid: reference values and diagnosis of PNPO deficiency in paediatric patients. Mol Genet Metab. 2008 Jun;94(2):173-7. doi: 10.1016/j.ymgme.2008.01.004. Epub 2008 Feb 21. [PubMed:18294893 ]
Sepiapterin reductase deficiency
  1. Verbeek MM, Willemsen MA, Wevers RA, Lagerwerf AJ, Abeling NG, Blau N, Thony B, Vargiami E, Zafeiriou DI: Two Greek siblings with sepiapterin reductase deficiency. Mol Genet Metab. 2008 Aug;94(4):403-9. doi: 10.1016/j.ymgme.2008.04.003. Epub 2008 May 27. [PubMed:18502672 ]
Bipolar disorder
  1. Ryden E, Johansson C, Blennow K, Landen M: Lower CSF HVA and 5-HIAA in bipolar disorder type 1 with a history of childhood ADHD. J Neural Transm (Vienna). 2009 Dec;116(12):1667-74. doi: 10.1007/s00702-009-0300-3. Epub 2009 Sep 12. [PubMed:19756368 ]
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 ]
Carbamoyl Phosphate Synthetase Deficiency
  1. Ishida J, Iizuka R, Yamaguchi M: High-performance liquid chromatographic determination of 5-hydroxyindoles by post-column fluorescence derivatization. Analyst. 1993 Feb;118(2):165-9. [PubMed:7680187 ]
Eosinophilic esophagitis
  1. Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Perillyl alcohol administration for cancer treatment
  1. Nam H, Chung BC, Kim Y, Lee K, Lee D: Combining tissue transcriptomics and urine metabolomics for breast cancer biomarker identification. Bioinformatics. 2009 Dec 1;25(23):3151-7. doi: 10.1093/bioinformatics/btp558. Epub 2009 Sep 25. [PubMed:19783829 ]
Metabolic syndrome
  1. Tulipani S, Llorach R, Jauregui O, Lopez-Uriarte P, Garcia-Aloy M, Bullo M, Salas-Salvado J, Andres-Lacueva C: Metabolomics unveils urinary changes in subjects with metabolic syndrome following 12-week nut consumption. J Proteome Res. 2011 Nov 4;10(11):5047-58. doi: 10.1021/pr200514h. Epub 2011 Sep 29. [PubMed:21905751 ]
Dopamine-serotonin Vesicular Transport Defect
  1. Rilstone JJ, Alkhater RA, Minassian BA: Brain dopamine-serotonin vesicular transport disease and its treatment. N Engl J Med. 2013 Feb 7;368(6):543-50. doi: 10.1056/NEJMoa1207281. Epub 2013 Jan 30. [PubMed:23363473 ]
Brunner Syndrome
  1. Brunner HG, Nelen MR, van Zandvoort P, Abeling NG, van Gennip AH, Wolters EC, Kuiper MA, Ropers HH, van Oost BA: X-linked borderline mental retardation with prominent behavioral disturbance: phenotype, genetic localization, and evidence for disturbed monoamine metabolism. Am J Hum Genet. 1993 Jun;52(6):1032-9. [PubMed:8503438 ]
Associated OMIM IDs
  • 181500 (Schizophrenia)
  • 608516 (Major depressive disorder)
  • 229300 (Friedreich's ataxia)
  • 182601 (Hereditary spastic paraplegia)
  • 608643 (Aromatic L-amino acid decarboxylase deficiency)
  • 212750 (Celiac disease)
  • 610090 (Pyridoxamine 5-prime-phosphate oxidase deficiency)
  • 182125 (Sepiapterin reductase deficiency)
  • 125480 (Bipolar disorder)
  • 266600 (Crohn's disease)
  • 237300 (Carbamoyl Phosphate Synthetase Deficiency)
  • 610247 (Eosinophilic esophagitis)
  • 605552 (Metabolic syndrome)
  • 300615 (Brunner Syndrome)
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB001403
KNApSAcK IDC00000104
Chemspider ID1760
KEGG Compound IDC05635
BioCyc ID5-HYDROXYINDOLE_ACETATE
BiGG ID46167
Wikipedia Link5-Hydroxyindoleacetic_acid
METLIN ID2975
PubChem Compound1826
PDB IDNot Available
ChEBI ID27823
Food Biomarker OntologyNot Available
VMH ID5HOXINDOA
MarkerDB IDMDB00000246
Good Scents IDrw1127791
References
Synthesis Reference Asero, B.; Colo, V. A.; Vercellone, A. Preparation of 5-hydroxy-3-indoleacetic acid. Farmaco, Edizione Scientifica (1956), 11 219-20.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
  2. Carpenter LL, Anderson GM, Siniscalchi JM, Chappell PB, Price LH: Acute changes in cerebrospinal fluid 5-HIAA following oral paroxetine challenge in healthy humans. Neuropsychopharmacology. 2003 Feb;28(2):339-47. [PubMed:12589387 ]
  3. Owens MJ, Nemeroff CB: Role of serotonin in the pathophysiology of depression: focus on the serotonin transporter. Clin Chem. 1994 Feb;40(2):288-95. [PubMed:7508830 ]
  4. Ilkhanizadeh B, Owji AA, Tavangar SM, Vasei M, Tabei SM: Spot urine 5-hydroxy indole acetic acid and acute appendicitis. Hepatogastroenterology. 2001 May-Jun;48(39):609-13. [PubMed:11462886 ]
  5. Rotondo A, Schuebel K, Bergen A, Aragon R, Virkkunen M, Linnoila M, Goldman D, Nielsen D: Identification of four variants in the tryptophan hydroxylase promoter and association to behavior. Mol Psychiatry. 1999 Jul;4(4):360-8. [PubMed:10483053 ]
  6. Walendzik H, Zimmer G, Skopp G: [Serotonin, 5-hydroxyindolylacetic acid and cholesterol content in blood, cerebrospinal fluid and brain areas for differentiation of suicidal from non-suicidal cause of death]. Arch Kriminol. 2000 May-Jun;205(5-6):131-44. [PubMed:10923167 ]
  7. Yamamoto M: Depression in Parkinson's disease: its prevalence, diagnosis, and neurochemical background. J Neurol. 2001 Sep;248 Suppl 3:III5-11. [PubMed:11697689 ]
  8. Mann JJ, McBride PA, Brown RP, Linnoila M, Leon AC, DeMeo M, Mieczkowski T, Myers JE, Stanley M: Relationship between central and peripheral serotonin indexes in depressed and suicidal psychiatric inpatients. Arch Gen Psychiatry. 1992 Jun;49(6):442-6. [PubMed:1376106 ]
  9. Christofides J, Bridel M, Egerton M, Mackay GM, Forrest CM, Stoy N, Darlington LG, Stone TW: Blood 5-hydroxytryptamine, 5-hydroxyindoleacetic acid and melatonin levels in patients with either Huntington's disease or chronic brain injury. J Neurochem. 2006 May;97(4):1078-88. Epub 2006 Mar 29. [PubMed:16573644 ]
  10. Celada P, Sarrias MJ, Artigas F: Serotonin and 5-hydroxyindoleacetic acid in plasma. Potential use as peripheral measures of MAO-A activity. J Neural Transm Suppl. 1990;32:149-54. [PubMed:1708403 ]
  11. Borg S, Kvande H, Liljeberg P, Mossberg D, Valverius P: 5-Hydroxyindoleacetic acid in cerebrospinal fluid in alcoholic patients under different clinical conditions. Alcohol. 1985 May-Jun;2(3):415-8. [PubMed:2411275 ]
  12. Feldman JM: Urinary serotonin in the diagnosis of carcinoid tumors. Clin Chem. 1986 May;32(5):840-4. [PubMed:2421946 ]
  13. Korpi ER, Kleinman JE, Goodman SI, Phillips I, DeLisi LE, Linnoila M, Wyatt RJ: Serotonin and 5-hydroxyindoleacetic acid in brains of suicide victims. Comparison in chronic schizophrenic patients with suicide as cause of death. Arch Gen Psychiatry. 1986 Jun;43(6):594-600. [PubMed:2423050 ]
  14. Fukuda H, Nakamura S, Hara K, Udaka F, Kameyama M: [Study on the concentration of 5-hydroxyindoleacetic acid (5-HIAA) in the lumbar cerebrospinal fluid (CSF) in neurological diseases]. Rinsho Shinkeigaku. 1989 Sep;29(9):1192-4. [PubMed:2480863 ]
  15. Meltzer H: Serotonergic dysfunction in depression. Br J Psychiatry Suppl. 1989 Dec;(8):25-31. [PubMed:2692637 ]
  16. Csernansky JG, Sheline YI: Abnormalities of serotonin metabolism and nonpsychotic psychiatric disorders. Ann Clin Psychiatry. 1993 Dec;5(4):275-81. [PubMed:8312985 ]
  17. Li JM, Kong LD, Wang YM, Cheng CH, Zhang WY, Tan WZ: Behavioral and biochemical studies on chronic mild stress models in rats treated with a Chinese traditional prescription Banxia-houpu decoction. Life Sci. 2003 Nov 21;74(1):55-73. [PubMed:14575813 ]
  18. Castejon AM, Paez X, Hernandez L, Cubeddu LX: Use of intravenous microdialysis to monitor changes in serotonin release and metabolism induced by cisplatin in cancer patients: comparative effects of granisetron and ondansetron. J Pharmacol Exp Ther. 1999 Dec;291(3):960-6. [PubMed:10565811 ]
  19. Lambert GW, Kaye DM, Cox HS, Vaz M, Turner AG, Jennings GL, Esler MD: Regional 5-hydroxyindoleacetic acid production in humans. Life Sci. 1995;57(3):255-67. [PubMed:7541101 ]

Enzymes

Enzyme Details
1. Acetylserotonin O-methyltransferase
General function:
Involved in O-methyltransferase activity
Specific function:
Isoform 1 catalyzes the transfer of a methyl group onto N-acetylserotonin, producing melatonin (N-acetyl-5-methoxytryptamine). Isoform 2 and isoform 3 lack enzyme activity.
Gene Name:
ASMT
Uniprot ID:
P46597
Molecular weight:
41660.34
Reactions
S-Adenosylmethionine + 5-Hydroxyindoleacetic acid → S-Adenosylhomocysteine + 5-Methoxyindoleacetatedetails
Enzyme Details
2. Aldehyde oxidase
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
AOX1
Uniprot ID:
Q06278
Molecular weight:
147916.735
Reactions
5-Hydroxyindoleacetaldehyde + Oxygen + Water → 5-Hydroxyindoleacetic acid + Hydrogen peroxidedetails
Enzyme Details
3. 4-trimethylaminobutyraldehyde dehydrogenase
General function:
Involved in oxidoreductase activity
Specific function:
Converts gamma-trimethylaminobutyraldehyde into gamma-butyrobetaine. Catalyzes the irreversible oxidation of a broad range of aldehydes to the corresponding acids in an NAD-dependent reaction.
Gene Name:
ALDH9A1
Uniprot ID:
P49189
Molecular weight:
56291.485
Reactions
5-Hydroxyindoleacetaldehyde + NAD + Water → 5-Hydroxyindoleacetic acid + Hydrogen Ion + NADHdetails
Enzyme Details
4. Alpha-aminoadipic semialdehyde dehydrogenase
General function:
Involved in oxidoreductase activity
Specific function:
Multifunctional enzyme mediating important protective effects. Metabolizes betaine aldehyde to betaine, an important cellular osmolyte and methyl donor. Protects cells from oxidative stress by metabolizing a number of lipid peroxidation-derived aldehydes. Involved in lysine catabolism.
Gene Name:
ALDH7A1
Uniprot ID:
P49419
Molecular weight:
58486.74
Reactions
5-Hydroxyindoleacetaldehyde + NAD + Water → 5-Hydroxyindoleacetic acid + Hydrogen Ion + NADHdetails
Enzyme Details
5. Aldehyde dehydrogenase family 1 member A3
General function:
Involved in oxidoreductase activity
Specific function:
Recognizes as substrates free retinal and cellular retinol-binding protein-bound retinal. Seems to be the key enzyme in the formation of an RA gradient along the dorso-ventral axis during the early eye development and also in the development of the olfactory system (By similarity).
Gene Name:
ALDH1A3
Uniprot ID:
P47895
Molecular weight:
56107.995
Enzyme Details
6. Aldehyde dehydrogenase, mitochondrial
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
ALDH2
Uniprot ID:
P05091
Molecular weight:
56380.93
Reactions
5-Hydroxyindoleacetaldehyde + NAD + Water → 5-Hydroxyindoleacetic acid + Hydrogen Ion + NADHdetails
Enzyme Details
7. Fatty aldehyde dehydrogenase
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidation of long-chain aliphatic aldehydes to fatty acids. Active on a variety of saturated and unsaturated aliphatic aldehydes between 6 and 24 carbons in length. Responsible for conversion of the sphingosine 1-phosphate (S1P) degradation product hexadecenal to hexadecenoic acid.
Gene Name:
ALDH3A2
Uniprot ID:
P51648
Molecular weight:
54847.36
Reactions
5-Hydroxyindoleacetaldehyde + NAD + Water → 5-Hydroxyindoleacetic acid + Hydrogen Ion + NADHdetails
Enzyme Details
8. Aldehyde dehydrogenase X, mitochondrial
General function:
Involved in oxidoreductase activity
Specific function:
ALDHs play a major role in the detoxification of alcohol-derived acetaldehyde. They are involved in the metabolism of corticosteroids, biogenic amines, neurotransmitters, and lipid peroxidation.
Gene Name:
ALDH1B1
Uniprot ID:
P30837
Molecular weight:
57248.96
Reactions
5-Hydroxyindoleacetaldehyde + NAD + Water → 5-Hydroxyindoleacetic acid + Hydrogen Ion + NADHdetails