Hmdb loader

Showing metabocard for Indoleacetic acid (HMDB0000197)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (7) Show 7 proteinsXML
enzymes (7) Show 7 proteins
Show more...Show more...Show more...Show more...Show more...Show more...Show more...
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:14:36 UTC
HMDB IDHMDB0000197
Secondary Accession Numbers
  • HMDB00197
Metabolite Identification
Common NameIndoleacetic acid
DescriptionIndoleacetic acid (IAA) is a breakdown product of tryptophan metabolism and is often produced by the action of bacteria in the mammalian gut. Higher levels of IAA are associated with bacteria from Clostridium species including C. stricklandii, C. lituseburense, C. subterminale, and C. putrefaciens (PMID: 12173102 ). IAA can be found in Agrobacterium, Azospirillum, Bacillus, Bradyrhizobium, Clostridium, Enterobacter, Pantoea, Pseudomonas, Rhizobium (PMID: 12173102 , PMID: 17555270 , PMID: 12147474 , PMID: 19400643 , PMID: 9450337 , PMID: 21397014 ) (https://link.springer.com/chapter/10.1007/978-1-4612-3084-7_7) (https://escholarship.org/uc/item/1bf1b5m3). Some endogenous production of IAA in mammalian tissues also occurs. It may be produced by the decarboxylation of tryptamine or the oxidative deamination of tryptophan. IAA frequently occurs at low levels in urine and has been found in elevated levels in the urine of patients with phenylketonuria (PMID: 13610897 ). IAA has also been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID: 22626821 ). Using material extracted from human urine, it was discovered by Kogl in 1933 that indoleacetic acid is also an important plant hormone (PMID: 13610897 ). Specifically, IAA is a member of the group of phytohormones called auxins. IAA is generally considered to be the most important native auxin. Plant cells synthesize IAA from tryptophan (Wikipedia ). IAA and some derivatives can be oxidized by horseradish peroxidase (HRP) into cytotoxic species. IAA is only toxic after oxidative decarboxylation; the effect of IAA/HRP is thought to be due in part to the formation of methylene-oxindole, which may conjugate with DNA bases and protein thiols. IAA/HRP could be used as the basis for targeted cancer, a potential new role for plant auxins in cancer therapy (PMID: 11163327 ).
Structure
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000197 (Indoleacetic acid)

  Mrv1652309272007322D          

 13 14  0  0  1  0            999 V2000
   -3.1806    2.0643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8950    2.4767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6095    2.0642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6096    1.2393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8951    0.8267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1805    1.2393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3960    0.9843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9110    1.6517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3959    2.3191    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1411    0.1996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3342    0.0280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0793   -0.7565    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7821    0.6410    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
  7  8  2  0  0  0  0
  6  7  1  0  0  0  0
  8  9  1  0  0  0  0
  1  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 13  2  0  0  0  0
 11 12  1  0  0  0  0
M  END
Download

3D MOL for HMDB0000197 (Indoleacetic acid)

HMDB0000197
     RDKit          3D
Indoleacetic acid
 22 23  0  0  0  0  0  0  0  0999 V2000
    2.1212   -0.6625    1.4322 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7217   -0.5866    0.3219 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9297   -1.2027    0.1052 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0847    0.1974   -0.7693 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7914    0.7740   -0.3189 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4992    2.0709    0.0361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7993    2.1400    0.3777 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3841    0.9267    0.2614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6851    0.4937    0.4947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0095   -0.8250    0.2900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0215   -1.6830   -0.1448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7178   -1.2678   -0.3825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3953    0.0677   -0.1738 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9758   -2.2280    0.1310 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7636    1.0410   -1.0050 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9224   -0.4620   -1.6543 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1849    2.9071    0.0451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3421    2.9825    0.6971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4302    1.1985    0.8351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0076   -1.2245    0.4543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2597   -2.7329   -0.3129 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0574   -1.9247   -0.7202 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
 12 13  2  0
 13  5  1  0
 13  8  1  0
  3 14  1  0
  4 15  1  0
  4 16  1  0
  6 17  1  0
  7 18  1  0
  9 19  1  0
 10 20  1  0
 11 21  1  0
 12 22  1  0
M  END
Download

3D SDF for HMDB0000197 (Indoleacetic acid)

  Mrv1652309272007322D          

 13 14  0  0  1  0            999 V2000
   -3.1806    2.0643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8950    2.4767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6095    2.0642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6096    1.2393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8951    0.8267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1805    1.2393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3960    0.9843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9110    1.6517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3959    2.3191    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1411    0.1996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3342    0.0280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0793   -0.7565    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7821    0.6410    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
  7  8  2  0  0  0  0
  6  7  1  0  0  0  0
  8  9  1  0  0  0  0
  1  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 13  2  0  0  0  0
 11 12  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000197

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)CC1=CNC2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C10H9NO2/c12-10(13)5-7-6-11-9-4-2-1-3-8(7)9/h1-4,6,11H,5H2,(H,12,13)

> <INCHI_KEY>
SEOVTRFCIGRIMH-UHFFFAOYSA-N

> <FORMULA>
C10H9NO2

> <MOLECULAR_WEIGHT>
175.184

> <EXACT_MASS>
175.063328537

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
17.735695939781067

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.87

> <JCHEM_LOGP>
1.709756098333333

> <ALOGPS_LOGS>
-2.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
16.189363501426207

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.661850493370194

> <JCHEM_POLAR_SURFACE_AREA>
53.089999999999996

> <JCHEM_REFRACTIVITY>
48.4521

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.38e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
β-indole-3-acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0000197 (Indoleacetic acid)

HMDB0000197
     RDKit          3D
Indoleacetic acid
 22 23  0  0  0  0  0  0  0  0999 V2000
    2.1212   -0.6625    1.4322 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7217   -0.5866    0.3219 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9297   -1.2027    0.1052 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0847    0.1974   -0.7693 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7914    0.7740   -0.3189 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4992    2.0709    0.0361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7993    2.1400    0.3777 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3841    0.9267    0.2614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6851    0.4937    0.4947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0095   -0.8250    0.2900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0215   -1.6830   -0.1448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7178   -1.2678   -0.3825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3953    0.0677   -0.1738 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9758   -2.2280    0.1310 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7636    1.0410   -1.0050 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9224   -0.4620   -1.6543 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1849    2.9071    0.0451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3421    2.9825    0.6971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4302    1.1985    0.8351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0076   -1.2245    0.4543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2597   -2.7329   -0.3129 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0574   -1.9247   -0.7202 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
 12 13  2  0
 13  5  1  0
 13  8  1  0
  3 14  1  0
  4 15  1  0
  4 16  1  0
  6 17  1  0
  7 18  1  0
  9 19  1  0
 10 20  1  0
 11 21  1  0
 12 22  1  0
M  END
Download

PDB for HMDB0000197 (Indoleacetic acid)

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0      -5.937   3.853   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.271   4.623   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -8.604   3.853   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -8.605   2.313   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -7.271   1.543   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.937   2.313   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.473   1.837   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.567   3.083   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      -4.472   4.329   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      -3.997   0.373   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.491   0.052   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -2.015  -1.412   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -1.460   1.197   0.000  0.00  0.00           O+0
CONECT    1    2    6    9                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    8    6   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8    1                                                       
CONECT   10    7   11                                                       
CONECT   11   10   13   12                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END
Download

3D PDB for HMDB0000197 (Indoleacetic acid)

COMPND    HMDB0000197
HETATM    1  O1  UNL     1       2.121  -0.662   1.432  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.722  -0.587   0.322  1.00  0.00           C  
HETATM    3  O2  UNL     1       3.930  -1.203   0.105  1.00  0.00           O  
HETATM    4  C2  UNL     1       2.085   0.197  -0.769  1.00  0.00           C  
HETATM    5  C3  UNL     1       0.791   0.774  -0.319  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.499   2.071   0.036  1.00  0.00           C  
HETATM    7  N1  UNL     1      -0.799   2.140   0.378  1.00  0.00           N  
HETATM    8  C5  UNL     1      -1.384   0.927   0.261  1.00  0.00           C  
HETATM    9  C6  UNL     1      -2.685   0.494   0.495  1.00  0.00           C  
HETATM   10  C7  UNL     1      -3.009  -0.825   0.290  1.00  0.00           C  
HETATM   11  C8  UNL     1      -2.021  -1.683  -0.145  1.00  0.00           C  
HETATM   12  C9  UNL     1      -0.718  -1.268  -0.383  1.00  0.00           C  
HETATM   13  C10 UNL     1      -0.395   0.068  -0.174  1.00  0.00           C  
HETATM   14  H1  UNL     1       3.976  -2.228   0.131  1.00  0.00           H  
HETATM   15  H2  UNL     1       2.764   1.041  -1.005  1.00  0.00           H  
HETATM   16  H3  UNL     1       1.922  -0.462  -1.654  1.00  0.00           H  
HETATM   17  H4  UNL     1       1.185   2.907   0.045  1.00  0.00           H  
HETATM   18  H5  UNL     1      -1.342   2.983   0.697  1.00  0.00           H  
HETATM   19  H6  UNL     1      -3.430   1.199   0.835  1.00  0.00           H  
HETATM   20  H7  UNL     1      -4.008  -1.225   0.454  1.00  0.00           H  
HETATM   21  H8  UNL     1      -2.260  -2.733  -0.313  1.00  0.00           H  
HETATM   22  H9  UNL     1       0.057  -1.925  -0.720  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   14
CONECT    4    5   15   16
CONECT    5    6    6   13
CONECT    6    7   17
CONECT    7    8   18
CONECT    8    9    9   13
CONECT    9   10   19
CONECT   10   11   11   20
CONECT   11   12   21
CONECT   12   13   13   22
END
Download

SMILES for HMDB0000197 (Indoleacetic acid)

OC(=O)CC1=CNC2=CC=CC=C12
Download

INCHI for HMDB0000197 (Indoleacetic acid)

InChI=1S/C10H9NO2/c12-10(13)5-7-6-11-9-4-2-1-3-8(7)9/h1-4,6,11H,5H2,(H,12,13)
Download
View in JSmolView Stereo Labels
Synonyms
Chemical FormulaC10H9NO2
Average Molecular Weight175.184
Monoisotopic Molecular Weight175.063328537
IUPAC Name2-(1H-indol-3-yl)acetic acid
Traditional Nameβ-indole-3-acetic acid
CAS Registry Number87-51-4
SMILES
OC(=O)CC1=CNC2=CC=CC=C12
InChI Identifier
InChI=1S/C10H9NO2/c12-10(13)5-7-6-11-9-4-2-1-3-8(7)9/h1-4,6,11H,5H2,(H,12,13)
InChI KeySEOVTRFCIGRIMH-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
  • Indole
  • Substituted pyrrole
  • Benzenoid
  • Heteroaromatic compound
  • Pyrrole
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Carbonyl group
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationSource
Process
Naturally occurring process
Role
Biological roleIndustrial application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point168.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.5 mg/mLNot Available
LogP1.41HANSCH,C ET AL. (1995)
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Baker138.10530932474
[M+H]+MetCCS_train_pos136.21330932474
[M+H]+Not Available136.8http://allccs.zhulab.cn/database/detail?ID=AllCCS00000463
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • Brain
  • Fibroblasts
  • Kidney
  • Liver
  • Placenta
  • Platelet
Pathways
Normal Concentrations
Abnormal Concentrations
Associated Disorders and Diseases
Disease References
Uremia
  1. Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24. [PubMed:22626821 ]
  2. Vanholder R, De Smet R, Glorieux G, Argiles A, Baurmeister U, Brunet P, Clark W, Cohen G, De Deyn PP, Deppisch R, Descamps-Latscha B, Henle T, Jorres A, Lemke HD, Massy ZA, Passlick-Deetjen J, Rodriguez M, Stegmayr B, Stenvinkel P, Tetta C, Wanner C, Zidek W: Review on uremic toxins: classification, concentration, and interindividual variability. Kidney Int. 2003 May;63(5):1934-43. doi: 10.1046/j.1523-1755.2003.00924.x. [PubMed:12675874 ]
Anorexia nervosa
  1. Anderson GM, Gerner RH, Cohen DJ, Fairbanks L: Central tryptamine turnover in depression, schizophrenia, and anorexia: measurement of indoleacetic acid in cerebrospinal fluid. Biol Psychiatry. 1984 Oct;19(10):1427-35. [PubMed:6518200 ]
Autism
  1. Anderson GM, Ross DL, Klykylo W, Feibel FC, Cohen DJ: Cerebrospinal fluid indoleacetic acid in autistic subjects. J Autism Dev Disord. 1988 Jun;18(2):259-62. [PubMed:3410814 ]
Major depressive disorder
  1. Anderson GM, Gerner RH, Cohen DJ, Fairbanks L: Central tryptamine turnover in depression, schizophrenia, and anorexia: measurement of indoleacetic acid in cerebrospinal fluid. Biol Psychiatry. 1984 Oct;19(10):1427-35. [PubMed:6518200 ]
Colorectal cancer
  1. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  2. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  3. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Tooth Decay
  1. Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Appendicitis
  1. 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 ]
Irritable bowel syndrome
  1. Bearcroft CP, Perrett D, Farthing MJ: Postprandial plasma 5-hydroxytryptamine in diarrhoea predominant irritable bowel syndrome: a pilot study. Gut. 1998 Jan;42(1):42-6. [PubMed:9505884 ]
Eosinophilic esophagitis
  1. Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Tryptophanuria with dwarfism
  1. TADA K, ITO H, WADA Y, ARAKAWA T: CONGENITAL TRYPTOPHANURIA WITH DWARFISM ("H" DISEASE-LIKE CLINICAL FEATURES WITHOUT INDICANURIA AND GENERALIZED AMINOACIDURIA):--A PROBABLY NEW INBORN ERROR OF TRYPTOPHAN METABOLISM. Tohoku J Exp Med. 1963 Jul 25;80:118-34. [PubMed:14055140 ]
Associated OMIM IDs
DrugBank IDDB07950
Phenol Explorer Compound IDNot Available
FooDB IDFDB030920
KNApSAcK IDC00000100
Chemspider ID780
KEGG Compound IDC00954
BioCyc IDINDOLE_ACETATE_AUXIN
BiGG IDNot Available
Wikipedia LinkIndole-3-acetic_acid
METLIN IDNot Available
PubChem Compound802
PDB IDNot Available
ChEBI ID16411
Food Biomarker OntologyNot Available
VMH IDIND3AC
MarkerDB IDMDB00013422
Good Scents IDNot Available
References
Synthesis Reference Snyder, H. R.; Pilgrim, Frederick J. Preparation of 3-indoleacetic acid; new synthesis of tryptophol. Journal of the American Chemical Society (1948), 70 3770-1.
Material Safety Data Sheet (MSDS)Not Available
General References

Enzymes

Enzyme Details
1. 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
Indoleacetaldehyde + NAD + Water → Indoleacetic acid + NADH + Hydrogen Iondetails
Enzyme Details
2. 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
Indoleacetaldehyde + NAD + Water → Indoleacetic acid + NADH + Hydrogen Iondetails
Enzyme Details
3. 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
4. Aldehyde dehydrogenase, mitochondrial
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
ALDH2
Uniprot ID:
P05091
Molecular weight:
56380.93
Reactions
Indoleacetaldehyde + NAD + Water → Indoleacetic acid + NADH + Hydrogen Iondetails
Enzyme Details
5. 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
Indoleacetaldehyde + NAD + Water → Indoleacetic acid + NADH + Hydrogen Iondetails
Enzyme Details
6. 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
Indoleacetaldehyde + NAD + Water → Indoleacetic acid + NADH + Hydrogen Iondetails
Enzyme Details
7. Aryl hydrocarbon receptor
General function:
Involved in transcription regulator activity
Specific function:
Ligand-activated transcriptional activator. Binds to the XRE promoter region of genes it activates. Activates the expression of multiple phase I and II xenobiotic chemical metabolizing enzyme genes (such as the CYP1A1 gene). Mediates biochemical and toxic effects of halogenated aromatic hydrocarbons. Involved in cell-cycle regulation. Likely to play an important role in the development and maturation of many tissues
Gene Name:
AHR
Uniprot ID:
P35869
Molecular weight:
96146.7