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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:46 UTC
Update Date2021-10-13 04:38:38 UTC
HMDB IDHMDB0002285
Secondary Accession Numbers
  • HMDB02285
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
Data?1582752241
Synonyms
ValueSource
2-IndolecarboxylateGenerator
indol-2-Carboxylic acidChEMBL, HMDB
indol-2-CarboxylateGenerator, HMDB
1H-Indole-2-carboxylateHMDB, Generator
1H-Indole-2-carboxylic acidHMDB
2-CarboxyindoleHMDB
Indole-2-carboxylateHMDB
Indole-2-carboxylic acidHMDB, MeSH
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 KeyHCUARRIEZVDMPT-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as indolecarboxylic acids and derivatives. Indolecarboxylic acids and derivatives 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
  • Pyrrole-2-carboxylic acid or derivatives
  • Substituted pyrrole
  • Benzenoid
  • Pyrrole
  • Heteroaromatic compound
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility719.9 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP2.31HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.78 g/LALOGPS
logP1.79ALOGPS
logP1.65ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)3.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area53.09 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity44.28 m³·mol⁻¹ChemAxon
Polarizability16.17 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+136.93531661259
DarkChem[M-H]-133.00231661259
DeepCCS[M+H]+131.67630932474
DeepCCS[M-H]-128.98530932474
DeepCCS[M-2H]-165.02330932474
DeepCCS[M+Na]+140.43230932474
AllCCS[M+H]+132.932859911
AllCCS[M+H-H2O]+128.332859911
AllCCS[M+NH4]+137.332859911
AllCCS[M+Na]+138.532859911
AllCCS[M-H]-130.432859911
AllCCS[M+Na-2H]-130.932859911
AllCCS[M+HCOO]-131.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-Indolecarboxylic acidOC(=O)C1=CC2=C(N1)C=CC=C23030.4Standard polar33892256
2-Indolecarboxylic acidOC(=O)C1=CC2=C(N1)C=CC=C21637.9Standard non polar33892256
2-Indolecarboxylic acidOC(=O)C1=CC2=C(N1)C=CC=C21750.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2-Indolecarboxylic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC2=CC=CC=C2[NH]11785.2Semi standard non polar33892256
2-Indolecarboxylic acid,1TMS,isomer #2C[Si](C)(C)N1C(C(=O)O)=CC2=CC=CC=C211835.6Semi standard non polar33892256
2-Indolecarboxylic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC2=CC=CC=C2N1[Si](C)(C)C1944.8Semi standard non polar33892256
2-Indolecarboxylic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC2=CC=CC=C2N1[Si](C)(C)C1883.7Standard non polar33892256
2-Indolecarboxylic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC2=CC=CC=C2N1[Si](C)(C)C1974.6Standard polar33892256
2-Indolecarboxylic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC2=CC=CC=C2[NH]12052.0Semi standard non polar33892256
2-Indolecarboxylic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C(C(=O)O)=CC2=CC=CC=C212080.3Semi standard non polar33892256
2-Indolecarboxylic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC2=CC=CC=C2N1[Si](C)(C)C(C)(C)C2314.1Semi standard non polar33892256
2-Indolecarboxylic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC2=CC=CC=C2N1[Si](C)(C)C(C)(C)C2302.1Standard non polar33892256
2-Indolecarboxylic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC2=CC=CC=C2N1[Si](C)(C)C(C)(C)C2250.3Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2-Indolecarboxylic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-01ox-4900000000-71da0f4b4d797e27273b2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Indolecarboxylic acid GC-MS (1 TMS) - 70eV, Positivesplash10-00y0-9770000000-1d97508714d0fc3382202017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Indolecarboxylic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Indolecarboxylic acid 10V, Positive-QTOFsplash10-03di-0900000000-f4554fa32e1dc60685f12016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Indolecarboxylic acid 20V, Positive-QTOFsplash10-014i-0900000000-4e4ee101de19b55dc5ff2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Indolecarboxylic acid 40V, Positive-QTOFsplash10-014i-1900000000-1568880a7641c60671902016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Indolecarboxylic acid 10V, Negative-QTOFsplash10-03di-0900000000-06e55ebe614b04ed5f752016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Indolecarboxylic acid 20V, Negative-QTOFsplash10-03xr-0900000000-958b289f26a6c0a5c47d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Indolecarboxylic acid 40V, Negative-QTOFsplash10-014l-2900000000-6698c24dd617648873c92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Indolecarboxylic acid 10V, Positive-QTOFsplash10-03di-0900000000-70e9cda69dd6169dc2a82021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Indolecarboxylic acid 20V, Positive-QTOFsplash10-01ox-0900000000-882a9335e9dcffc135e22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Indolecarboxylic acid 40V, Positive-QTOFsplash10-014l-3900000000-975d31c56ec06b8fadb12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Indolecarboxylic acid 10V, Negative-QTOFsplash10-014i-0900000000-89c3f30c8225ba6d5d622021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Indolecarboxylic acid 20V, Negative-QTOFsplash10-014i-0900000000-89c3f30c8225ba6d5d622021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Indolecarboxylic acid 40V, Negative-QTOFsplash10-014i-0900000000-89c3f30c8225ba6d5d622021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified6.228 +/- 5.119 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Analysis of 30 no...
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022948
KNApSAcK IDNot Available
Chemspider ID65731
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6593
PubChem Compound72899
PDB IDNot Available
ChEBI ID130363
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1251471
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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:9046331 ]