Record Information |
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Version | 1.0 |
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Created at | 2020-11-23 18:25:27 UTC |
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Updated at | 2021-08-12 19:51:40 UTC |
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NP-MRD ID | NP0002621 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Isonicotinic acid |
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Provided By | BMRB |
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Description | Isonicotinic acid, also known as 4-carboxypyridine or gamma-picolinic acid, belongs to the class of organic compounds known as pyridinecarboxylic acids. Pyridinecarboxylic acids are compounds containing a pyridine ring bearing a carboxylic acid group. Isonicotinic acid is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Isonicotinic acid is found in Aloe africana, Arabidopsis thaliana and Chlamydomonas reinhardtii. It was first documented in 1953 (PMID: 13115353). Based on a literature review a significant number of articles have been published on Isonicotinic acid (PMID: 17984079) (PMID: 22537922) (PMID: 23832340) (PMID: 23929452). |
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Structure | InChI=1S/C6H5NO2/c8-6(9)5-1-3-7-4-2-5/h1-4H,(H,8,9) |
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Synonyms | Value | Source |
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4-Carboxypyridine | ChEBI | 4-Pyridinecarboxylic acid | ChEBI | gamma-Picolinic acid | ChEBI | gamma-Pyridinecarboxylic acid | ChEBI | p-Pyridinecarboxylic acid | ChEBI | 4-Pyridinecarboxylate | Generator | g-Picolinate | Generator | g-Picolinic acid | Generator | gamma-Picolinate | Generator | Γ-picolinate | Generator | Γ-picolinic acid | Generator | g-Pyridinecarboxylate | Generator | g-Pyridinecarboxylic acid | Generator | gamma-Pyridinecarboxylate | Generator | Γ-pyridinecarboxylate | Generator | Γ-pyridinecarboxylic acid | Generator | p-Pyridinecarboxylate | Generator | Isonicotinate | Generator | Acid, isonicotinic | HMDB | Acids, isonicotinic | HMDB | Isonicotinic acids | HMDB |
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Chemical Formula | C6H5NO2 |
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Average Mass | 123.1094 Da |
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Monoisotopic Mass | 123.03203 Da |
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IUPAC Name | pyridine-4-carboxylic acid |
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Traditional Name | isonicotinic acid |
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CAS Registry Number | Not Available |
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SMILES | OC(=O)C1=CC=NC=C1 |
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InChI Identifier | InChI=1S/C6H5NO2/c8-6(9)5-1-3-7-4-2-5/h1-4H,(H,8,9) |
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InChI Key | TWBYWOBDOCUKOW-UHFFFAOYSA-N |
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Experimental Spectra |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, 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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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as pyridinecarboxylic acids. Pyridinecarboxylic acids are compounds containing a pyridine ring bearing a carboxylic acid group. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Pyridines and derivatives |
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Sub Class | Pyridinecarboxylic acids and derivatives |
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Direct Parent | Pyridinecarboxylic acids |
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Alternative Parents | |
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Substituents | - Pyridine carboxylic acid
- Heteroaromatic compound
- Azacycle
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organic nitrogen compound
- Organic oxygen compound
- Organopnictogen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Organonitrogen compound
- Aromatic heteromonocyclic compound
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Molecular Framework | Aromatic heteromonocyclic compounds |
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External Descriptors | |
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Physical Properties |
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State | Not Available |
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Experimental Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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General References | - Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]
- CUTHBERTSON WF, IRELAND DM, WOLFF W: Detection and identification of some metabolites of isonicotinic acid hydrazide (isoniazid) in human urine. Biochem J. 1953 Nov;55(4):669-71. doi: 10.1042/bj0550669. [PubMed:13115353 ]
- Sharma NN, Sharma M, Bhalla TC: Nocardia globerula NHB-2 nitrilase catalysed biotransformation of 4-cyanopyridine to isonicotinic acid. AMB Express. 2012 Apr 26;2(1):25. doi: 10.1186/2191-0855-2-25. [PubMed:22537922 ]
- Ida C, Ogata S: Changes in NAD content induced by nicotinic acid-related compounds in K562 cells during differentiation. Biosci Biotechnol Biochem. 2013;77(7):1583-5. doi: 10.1271/bbb.130131. Epub 2013 Jul 7. [PubMed:23832340 ]
- Hong SP, Lusiak BD, Burback BL, Johnson JD: Evaluations of in vitro metabolism, drug-drug interactions mediated by reversible and time-dependent inhibition of CYPs, and plasma protein binding of MMB4 DMS. Int J Toxicol. 2013 Jul-Aug;32(4 Suppl):75S-87S. doi: 10.1177/1091581813487226. [PubMed:23929452 ]
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