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Showing NP-Card for 5-Hydroxyindoleacetic acid (NP0000098)

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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-08-16 18:04:09 UTC
NP-MRD IDNP0000098
Secondary Accession NumbersNone
Natural Product 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
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000098 (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
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3D MOL for NP0000098 (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 NP0000098 (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>
NP0000098

> <DATABASE_NAME>
NP-MRD

> <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

$$$$
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3D-SDF for NP0000098 (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

PDB for NP0000098 (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 NP0000098 (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 NP0000098 (5-Hydroxyindoleacetic acid)

OC(=O)CC1=CNC2=C1C=C(O)C=C2
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INCHI for NP0000098 (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 JSmol
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
Acid, 5-hydroxyindolamine aceticHMDB
Acid, hydroxyindoleaceticHMDB
5 Hydroxy 3 indoleacetic acidHMDB
5-Hydroxy-3-indoleacetic acidHMDB
Acetic acid, 5-hydroxyindolamineHMDB
5 Hydroxyindolamine acetic acidHMDB
5-Hydroxyindolamine acetic acidHMDB
Acid, 5-hydroxy-3-indoleaceticHMDB
Hydroxyindoleacetic acidHMDB
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
Chemical FormulaC10H9NO3
Average Mass191.1834 Da
Monoisotopic Mass191.05824 Da
IUPAC Name2-(5-hydroxy-1H-indol-3-yl)acetic acid
Traditional Namehydroxyindoleacetic acid
CAS Registry Number54-16-0
SMILES
OC(=O)CC1=CNC2=CC=C(O)C=C12
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Cryptocarya pyriformisPlant
Daphnia pulexLOTUS Database
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Griffonia simplicifoliaLOTUS Database
Homo sapiensLOTUS Database
Homo sapiens (Urine)Animalia
Hordeum vulgareFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Litoria verreauxiiLOTUS Database
Lolium perennePlant
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Mus musculusLOTUS Database
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Solanum lycopersicumPlant
Solanum lycopersicum var. lycopersicumFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Trypanosoma bruceiLOTUS Database
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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point161 - 163 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility24 mg/mLNot Available
LogPNot AvailableNot Available
Predicted 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
HMDB IDHMDB0000763
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030574
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
Good Scents IDrw1127791
References
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. Yamamoto M: Depression in Parkinson's disease: its prevalence, diagnosis, and neurochemical background. J Neurol. 2001 Sep;248 Suppl 3:III5-11. [PubMed:11697689 ]
  7. 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 ]
  8. 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 ]
  9. 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 ]
  10. 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 ]
  11. Feldman JM: Urinary serotonin in the diagnosis of carcinoid tumors. Clin Chem. 1986 May;32(5):840-4. [PubMed:2421946 ]
  12. 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 ]
  13. 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 ]
  14. Meltzer H: Serotonergic dysfunction in depression. Br J Psychiatry Suppl. 1989 Dec;(8):25-31. [PubMed:2692637 ]
  15. Csernansky JG, Sheline YI: Abnormalities of serotonin metabolism and nonpsychotic psychiatric disorders. Ann Clin Psychiatry. 1993 Dec;5(4):275-81. [PubMed:8312985 ]
  16. 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 ]
  17. 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 ]
  18. 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 ]