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Record Information
Version3.6
Creation Date2006-05-22 14:17:46 UTC
Update Date2016-02-11 01:05:32 UTC
HMDB IDHMDB02285
Secondary Accession NumbersNone
Metabolite Identification
Common Name2-Indolecarboxylic acid
Description2-Indolecarboxylic acid is a strong inhibitor of lipid peroxidation, similar to melatonin and some structurally related indole compounds. Lipid peroxidation with tert-butyl hydroperoxide is a source of free radicals (PMID 12236544 ). 2-Indolecarboxylic acid is a phenolic components known to exist in Korean ginseng (Koryo Insam Hakhoechi (1996), 20(3), 284-290) and brown rice (Han'guk Nonghwa Hakhoechi (1995), 38(5), 478-83).
Structure
Thumb
Synonyms
ValueSource
indol-2-Carboxylic acidChEMBL
indol-2-CarboxylateGenerator
Indole-2-carboxylateGenerator
1H-Indole-2-carboxylateHMDB
1H-Indole-2-carboxylic acidHMDB
2-CarboxyindoleHMDB
2-IndolecarboxylateHMDB
Chemical FormulaC9H7NO2
Average Molecular Weight161.1574
Monoisotopic Molecular Weight161.047678473
IUPAC Name1H-indole-2-carboxylic acid
Traditional Nameindole-2-carboxylic acid
CAS Registry Number1477-50-5
SMILES
OC(=O)C1=CC2=C(N1)C=CC=C2
InChI Identifier
InChI=1S/C9H7NO2/c11-9(12)8-5-6-3-1-2-4-7(6)10-8/h1-5,10H,(H,11,12)
InChI KeyInChIKey=HCUARRIEZVDMPT-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as indolecarboxylic acids and derivatives. These are compounds containing a carboxylic acid group (or a derivative thereof) linked to an indole.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndolecarboxylic acids and derivatives
Direct ParentIndolecarboxylic acids and derivatives
Alternative Parents
Substituents
  • Indolecarboxylic acid derivative
  • Indole
  • Pyrrole-2-carboxylic acid or derivatives
  • Pyrrole-2-carboxylic acid
  • Benzenoid
  • Substituted pyrrole
  • Heteroaromatic compound
  • Pyrrole
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP2.31HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility1.78 mg/mLALOGPS
logP1.79ALOGPS
logP1.65ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)3.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area53.09 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity44.28 m3·mol-1ChemAxon
Polarizability16.17 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified6.228 +/- 5.119 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022948
KNApSAcK IDNot Available
Chemspider ID65731
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB02285
Metagene LinkHMDB02285
METLIN ID6593
PubChem Compound72899
PDB IDNot Available
ChEBI ID130363
References
Synthesis ReferenceFeng, Liu-xing; Ding, Shao-min; Song, Hua-fu. Synthesis process of indole-2-carboxylic acid. Huaxue Yu Nianhe (2003), (4), 196-197.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Seal AN, Pratley JE, Haig T, An M: Identification and quantitation of compounds in a series of allelopathic and non-allelopathic rice root exudates. J Chem Ecol. 2004 Aug;30(8):1647-62. [15537165 ]
  2. Eaton RW, Chapman PJ: Formation of indigo and related compounds from indolecarboxylic acids by aromatic acid-degrading bacteria: chromogenic reactions for cloning genes encoding dioxygenases that act on aromatic acids. J Bacteriol. 1995 Dec;177(23):6983-8. [7592495 ]
  3. Cross PE, Dickinson RP, Parry MJ, Randall MJ: Selective thromboxane synthetase inhibitors. 3. 1H-imidazol-1-yl-substituted benzo[b]furan-, benzo[b]thiophene-, and indole-2- and -3-carboxylic acids. J Med Chem. 1986 Sep;29(9):1637-43. [3746813 ]
  4. Kawa K: Distribution and functional properties of 5-HT3 receptors in the rat hippocampal dentate gyrus: a patch-clamp study. J Neurophysiol. 1994 May;71(5):1935-47. [7520482 ]
  5. Stetinova V, Smetanova L, Grossmann V, Anzenbacher P: In vitro and in vivo assessment of the antioxidant activity of melatonin and related indole derivatives. Gen Physiol Biophys. 2002 Jun;21(2):153-62. [12236544 ]
  6. Showalter HD, Sercel AD, Leja BM, Wolfangel CD, Ambroso LA, Elliott WL, Fry DW, Kraker AJ, Howard CT, Lu GH, Moore CW, Nelson JM, Roberts BJ, Vincent PW, Denny WA, Thompson AM: Tyrosine kinase inhibitors. 6. Structure-activity relationships among N- and 3-substituted 2,2'-diselenobis(1H-indoles) for inhibition of protein tyrosine kinases and comparative in vitro and in vivo studies against selected sulfur congeners. J Med Chem. 1997 Feb 14;40(4):413-26. [9046331 ]