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Record Information
Version1.0
Created at2006-05-22 15:12:50 UTC
Updated at2021-08-19 23:58:51 UTC
NP-MRD IDNP0001160
Secondary Accession NumbersNone
Natural Product Identification
Common NameIndole-3-carboxylic acid
DescriptionIndole-3-carboxylic acid, also known as 3-carboxyindole or 3-indolecarboxylate, 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. Naphthylmethylindoles: Any compound containing a 1H-indol-3-yl-(1-naphthyl)methane structure with substitution at the nitrogen atom of the indole ring by an alkyl, haloalkyl, alkenyl, cycloalkylmethyl, cycloalkylethyl, 1-(N-methyl-2-piperidinyl)methyl, or 2-(4-morpholinyl)ethyl group whether or not further substituted in the indole ring to any extent and whether or not substituted in the naphthyl ring to any extent. One example given is JWH-250. Outside of the human body, indole-3-carboxylic acid has been detected, but not quantified in several different foods, such as brassicas, broccoli, pulses, common beets, and barley. This could make indole-3-carboxylic acid a potential biomarker for the consumption of these foods. Notice the pentyl group substituted onto the nitrogen atom of the indole ring. Note that this definition encompasses only those compounds that have OH groups attached to both the phenyl and the cyclohexyl rings, and so does not include compounds such as O-1871 which lacks the cyclohexyl OH group, or compounds such as JWH-337 or JWH-344 which lack the phenolic OH group.
Structure
Thumb
Synonyms
ValueSource
Indole-3-carboxylateGenerator
3-CarboxyindoleHMDB
1H-Indole-3-carboxylateHMDB
1H-Indole-3-carboxylic acidHMDB
3-Indole carboxylic acidHMDB
3-IndolecarboxylateHMDB
3-Indolecarboxylic acidHMDB
3-IndoleformateHMDB
3-Indoleformic acidHMDB
3-IndolylcarboxylateHMDB
3-Indolylcarboxylic acidHMDB
Indole - 3 carboxylateHMDB
Indole - 3 carboxylic acidHMDB
Indole-3-carboxylicacidHMDB
Indole-3-carboxylic acidKEGG
Indole-b-carboxylateGenerator
Indole-b-carboxylic acidGenerator
Indole-beta-carboxylateGenerator
Indole-β-carboxylateGenerator
Indole-β-carboxylic acidGenerator
Chemical FormulaC9H7NO2
Average Mass161.1574 Da
Monoisotopic Mass161.04768 Da
IUPAC Name1H-indole-3-carboxylic acid
Traditional Nameindole - 3 carboxylic acid
CAS Registry Number771-50-6
SMILES
OC(=O)C1=CNC2=CC=CC=C12
InChI Identifier
InChI=1S/C9H7NO2/c11-9(12)7-5-10-8-4-2-1-3-6(7)8/h1-5,10H,(H,11,12)
InChI KeyKMAKOBLIOCQGJP-UHFFFAOYSA-N
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, Methanol, simulated)Varshavi.d262021-08-17View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, Methanol, experimental)Varshavi.d262021-08-17View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, Methanol, simulated)Varshavi.d262021-08-17View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, Methanol, experimental)Varshavi.d262021-08-17View Spectrum
Species
Species of Origin
Species NameSourceReference
Arabidopsis thalianaKNApSAcK Database
Begonia nantoensisKNApSAcK Database
Beta vulgarisKNApSAcK Database
Cucumis sativus L.KNApSAcK Database
Houttuynia cordataKNApSAcK Database
Nicotiana tabacumKNApSAcK Database
Pinus sylvestrisKNApSAcK Database
Pisum sativumKNApSAcK Database
Pyrus malusKNApSAcK Database
Taraxacum formosanumKNApSAcK Database
Species Where Detected
Species NameSourceReference
Haliclona oculataKNApSAcK Database
Undaria pinnatifidaKNApSAcK Database
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-3-carboxylic acid
  • Pyrrole-3-carboxylic acid or derivatives
  • Substituted pyrrole
  • Benzenoid
  • Pyrrole
  • Heteroaromatic compound
  • Vinylogous amide
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Carboxylic acid
  • Azacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point206.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1351 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.99HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility2.42 g/LALOGPS
logP1.79ALOGPS
logP1.73ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)3.52ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area53.09 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity44.4 m³·mol⁻¹ChemAxon
Polarizability15.96 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
External Links
HMDB IDHMDB0003320
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000935
KNApSAcK IDC00000113
Chemspider ID63063
KEGG Compound IDC19837
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkStructural scheduling of synthetic cannabinoids
METLIN ID3795
PubChem Compound69867
PDB IDNot Available
ChEBI ID24809
Good Scents IDrw1251531
References
General References
  1. Liebich HM, Forst C: Basic profiles of organic acids in urine. J Chromatogr. 1990 Jan 26;525(1):1-14. [PubMed:2338430 ]
  2. HARTMANN F, FREIBERG E, RUGE W: [Indolepatterns in the urine of liver patients]. Klin Wochenschr. 1962 Jul 15;40:721-9. [PubMed:13905029 ]
  3. Byrd DJ, Kochen W, Idzko D, Knorr E: The analysis of indolic tryptophan metabolites in human urine. Thin-layer chromatography and in situ quantitation. J Chromatogr. 1974 Jul 17;94(0):85-106. [PubMed:4844607 ]
  4. Davis PJ, Gustafson ME, Rosazza JP: Formation of indole-3-carboxylic acid by Chromobacterium violaceum. J Bacteriol. 1976 Apr;126(1):544-6. doi: 10.1128/jb.126.1.544-546.1976. [PubMed:1262308 ]
  5. Lacan G, Magnus V, Simaga S, Iskric S, Hall PJ: Metabolism of tryptophol in higher and lower plants. Plant Physiol. 1985 Jul;78(3):447-54. doi: 10.1104/pp.78.3.447. [PubMed:16664264 ]