Record Information |
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Version | 1.0 |
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Created at | 2006-05-22 15:12:50 UTC |
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Updated at | 2021-10-07 20:40:59 UTC |
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NP-MRD ID | NP0001160 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Indole-3-carboxylic acid |
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Description | Indole-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. |
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Structure | InChI=1S/C9H7NO2/c11-9(12)7-5-10-8-4-2-1-3-6(7)8/h1-5,10H,(H,11,12) |
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Synonyms | Value | Source |
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Indole-3-carboxylate | Generator | 3-Carboxyindole | HMDB | 1H-Indole-3-carboxylate | HMDB | 1H-Indole-3-carboxylic acid | HMDB | 3-Indole carboxylic acid | HMDB | 3-Indolecarboxylate | HMDB | 3-Indolecarboxylic acid | HMDB | 3-Indoleformate | HMDB | 3-Indoleformic acid | HMDB | 3-Indolylcarboxylate | HMDB | 3-Indolylcarboxylic acid | HMDB | Indole - 3 carboxylate | HMDB | Indole - 3 carboxylic acid | HMDB | Indole-3-carboxylicacid | HMDB | Indole-b-carboxylate | HMDB | Indole-b-carboxylic acid | HMDB | Indole-beta-carboxylate | HMDB | Indole-β-carboxylate | HMDB | Indole-β-carboxylic acid | HMDB | Indole-3-carboxylic acid | KEGG |
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Chemical Formula | C9H7NO2 |
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Average Mass | 161.1574 Da |
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Monoisotopic Mass | 161.04768 Da |
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IUPAC Name | 1H-indole-3-carboxylic acid |
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Traditional Name | indole - 3 carboxylic acid |
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CAS Registry Number | 771-50-6 |
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SMILES | OC(=O)C1=CNC2=CC=CC=C12 |
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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) |
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InChI Key | KMAKOBLIOCQGJP-UHFFFAOYSA-N |
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Experimental Spectra |
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| Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 1H NMR Spectrum (1D, 600 MHz, Methanol, simulated) | Varshavi.d26 | | | 2021-08-17 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, Methanol, experimental) | Varshavi.d26 | | | 2021-08-17 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, Methanol, simulated) | Varshavi.d26 | | | 2021-08-17 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, Methanol, experimental) | Varshavi.d26 | | | 2021-08-17 | View Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
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| Not Available | Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | |
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Species Where Detected | |
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Chemical Taxonomy |
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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. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Indoles and derivatives |
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Sub Class | Indolecarboxylic acids and derivatives |
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Direct Parent | Indolecarboxylic acids and derivatives |
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Alternative Parents | |
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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
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | 206.5 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 1351 mg/L @ 25 °C (est) | The Good Scents Company Information System | LogP | 1.99 | Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995). |
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Predicted Properties | |
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General References | - Liebich HM, Forst C: Basic profiles of organic acids in urine. J Chromatogr. 1990 Jan 26;525(1):1-14. [PubMed:2338430 ]
- HARTMANN F, FREIBERG E, RUGE W: [Indolepatterns in the urine of liver patients]. Klin Wochenschr. 1962 Jul 15;40:721-9. [PubMed:13905029 ]
- 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 ]
- 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 ]
- 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 ]
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