| Record Information |
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| Version | 1.0 |
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| Creation Date | 2016-05-25 18:50:37 UTC |
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| Update Date | 2016-11-09 01:17:34 UTC |
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| Accession Number | CHEM022745 |
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| Identification |
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| Common Name | 2-Indolecarboxylic acid |
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| Class | Small Molecule |
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| Description | 2-Indolecarboxylic acid, also known as indol-2-carboxylate or 2-carboxyindole, 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. 2-Indolecarboxylic acid is possibly soluble (in water) and a weakly acidic compound (based on its pKa). |
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| Contaminant Sources | - FooDB Chemicals
- HMDB Contaminants - Urine
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| Contaminant Type | Not Available |
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| Chemical Structure | |
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| Synonyms | | Value | Source |
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| 2-Indolecarboxylate | Generator | | indol-2-Carboxylic acid | ChEMBL, HMDB | | indol-2-Carboxylate | Generator, HMDB | | 1H-Indole-2-carboxylate | HMDB, Generator | | 1H-Indole-2-carboxylic acid | HMDB | | 2-Carboxyindole | HMDB | | Indole-2-carboxylate | HMDB | | Indole-2-carboxylic acid | HMDB, MeSH |
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| Chemical Formula | C9H7NO2 |
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| Average Molecular Mass | 161.157 g/mol |
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| Monoisotopic Mass | 161.048 g/mol |
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| CAS Registry Number | 1477-50-5 |
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| IUPAC Name | 1H-indole-2-carboxylic acid |
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| Traditional Name | indole-2-carboxylic acid |
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| SMILES | OC(=O)C1=CC2=C(N1)C=CC=C2 |
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| 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) |
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| InChI Key | HCUARRIEZVDMPT-UHFFFAOYSA-N |
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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-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
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| Molecular Framework | Aromatic heteropolycyclic compounds |
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| External Descriptors | Not Available |
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| Biological Properties |
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| Status | Detected and Not Quantified |
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| Origin | Not Available |
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| Cellular Locations | Not Available |
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| Biofluid Locations | Not Available |
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| Tissue Locations | Not Available |
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| Pathways | Not Available |
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| Applications | Not Available |
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| Biological Roles | Not Available |
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| Chemical Roles | Not Available |
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| Physical Properties |
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| State | Not Available |
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| Appearance | Not Available |
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| Experimental Properties | | Property | Value |
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| Melting Point | Not Available | | Boiling Point | Not Available | | Solubility | Not Available |
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| Predicted Properties | |
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| Spectra |
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| Spectra | | Spectrum Type | Description | Splash Key | View |
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| Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-01ox-4900000000-71da0f4b4d797e27273b | Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-00y0-9770000000-1d97508714d0fc338220 | Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-03di-0900000000-f4554fa32e1dc60685f1 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-014i-0900000000-4e4ee101de19b55dc5ff | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-014i-1900000000-1568880a7641c6067190 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03di-0900000000-06e55ebe614b04ed5f75 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-03xr-0900000000-958b289f26a6c0a5c47d | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-014l-2900000000-6698c24dd617648873c9 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-03di-0900000000-70e9cda69dd6169dc2a8 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-01ox-0900000000-882a9335e9dcffc135e2 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-014l-3900000000-975d31c56ec06b8fadb1 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-014i-0900000000-89c3f30c8225ba6d5d62 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-014i-0900000000-89c3f30c8225ba6d5d62 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-014i-0900000000-89c3f30c8225ba6d5d62 | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum |
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| Toxicity Profile |
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| Route of Exposure | Not Available |
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| Mechanism of Toxicity | Not Available |
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| Metabolism | Not Available |
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| Toxicity Values | Not Available |
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| Lethal Dose | Not Available |
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| Carcinogenicity (IARC Classification) | Not Available |
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| Uses/Sources | Not Available |
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| Minimum Risk Level | Not Available |
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| Health Effects | Not Available |
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| Symptoms | Not Available |
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| Treatment | Not Available |
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| Concentrations |
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| Not Available |
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| External Links |
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| DrugBank ID | Not Available |
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| HMDB ID | HMDB0002285 |
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| FooDB ID | FDB022948 |
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| Phenol Explorer ID | Not Available |
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| KNApSAcK ID | Not Available |
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| BiGG ID | Not Available |
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| BioCyc ID | Not Available |
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| METLIN ID | 6593 |
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| PDB ID | Not Available |
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| Wikipedia Link | Not Available |
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| Chemspider ID | 65731 |
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| ChEBI ID | 130363 |
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| PubChem Compound ID | 72899 |
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| Kegg Compound ID | Not Available |
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| YMDB ID | Not Available |
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| ECMDB ID | Not Available |
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| References |
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| Synthesis Reference | Not Available |
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| MSDS | Not Available |
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| General References | | 1. Feng, Liu-xing; Ding, Shao-min; Song, Hua-fu. Synthesis process of indole-2-carboxylic acid. Huaxue Yu Nianhe (2003), (4), 196-197. | | 2. Qian L, Zhao A, Zhang Y, Chen T, Zeisel SH, Jia W, Cai W: Metabolomic Approaches to Explore Chemical Diversity of Human Breast-Milk, Formula Milk and Bovine Milk. Int J Mol Sci. 2016 Dec 17;17(12). pii: ijms17122128. doi: 10.3390/ijms17122128. | | 3. Feng, Liu-xing; Ding, Shao-min; Song, Hua-fu. Synthesis process of indole-2-carboxylic acid. Huaxue Yu Nianhe (2003), (4), 196-197. | | 4. 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. | | 5. 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. | | 6. 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. | | 7. 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. | | 8. 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. | | 9. 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. |
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