Record Information |
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Version | 2.0 |
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Created at | 2020-11-23 18:25:13 UTC |
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Updated at | 2021-08-12 19:51:39 UTC |
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NP-MRD ID | NP0002611 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Chorismic acid |
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Provided By | BMRB |
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Description | Chorismate, also known as chorismic acid, belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups. Chorismate exists in all living species, ranging from bacteria to plants to humans. Chorismate is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Chorismic acid is found in Klebsiella pneumonia, Paraburkholderia phymatum, Streptomyces albidoflavus and Streptomyces griseus. Chorismic acid was first documented in 1964 (PMID: 5834235). Based on a literature review a small amount of articles have been published on Chorismate (PMID: 11745165) (PMID: 23757404) (PMID: 4897776). |
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Structure | O[C@@H]1C=CC(=C[C@H]1OC(=C)C(O)=O)C(O)=O InChI=1S/C10H10O6/c1-5(9(12)13)16-8-4-6(10(14)15)2-3-7(8)11/h2-4,7-8,11H,1H2,(H,12,13)(H,14,15)/t7-,8-/m1/s1 |
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Synonyms | Value | Source |
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(3R,4R)-3-[(1-Carboxyvinyl)oxy]-4-hydroxycyclohexa-1,5-diene-1-carboxylic acid | ChEBI | (3R-trans)-3-((1-Carboxyethenyl)oxy)-4-hydroxy-1,5-cyclohexadiene-1-carboxylic acid | ChEBI | Chorismic acid | Kegg | (3R,4R)-3-[(1-Carboxyethenyl)oxy]-4-hydroxycyclohexa-1,5-diene-1-carboxylate | Kegg | (3R,4R)-3-[(1-Carboxyvinyl)oxy]-4-hydroxycyclohexa-1,5-diene-1-carboxylate | Generator | (3R-trans)-3-((1-Carboxyethenyl)oxy)-4-hydroxy-1,5-cyclohexadiene-1-carboxylate | Generator | (3R,4R)-3-[(1-Carboxyethenyl)oxy]-4-hydroxycyclohexa-1,5-diene-1-carboxylic acid | Generator | Acid, chorismic | MeSH, HMDB | (-)-Chorismic acid | HMDB | (3R,4R)-3-[(1-Carboxyethenyl)oxy]-4-hydroxy-1,5-cyclohexadiene-1-carboxylic acid | HMDB | (3R-trans)-3-(1-Carboxyvinyloxy)-4-hydroxy-1,5-cyclohexadiene-1-carboxylic acid | HMDB |
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Chemical Formula | C10H10O6 |
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Average Mass | 226.1828 Da |
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Monoisotopic Mass | 226.04774 Da |
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IUPAC Name | (3R,4R)-3-[(1-carboxyeth-1-en-1-yl)oxy]-4-hydroxycyclohexa-1,5-diene-1-carboxylic acid |
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Traditional Name | chorismic acid |
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CAS Registry Number | Not Available |
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SMILES | O[C@@H]1C=CC(=C[C@H]1OC(=C)C(O)=O)C(O)=O |
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InChI Identifier | InChI=1S/C10H10O6/c1-5(9(12)13)16-8-4-6(10(14)15)2-3-7(8)11/h2-4,7-8,11H,1H2,(H,12,13)(H,14,15)/t7-,8-/m1/s1 |
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InChI Key | WTFXTQVDAKGDEY-HTQZYQBOSA-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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Species Where Detected | |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Carboxylic acids and derivatives |
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Sub Class | Dicarboxylic acids and derivatives |
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Direct Parent | Dicarboxylic acids and derivatives |
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Alternative Parents | |
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Substituents | - Dicarboxylic acid or derivatives
- Secondary alcohol
- Carboxylic acid
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Alcohol
- Aliphatic homomonocyclic compound
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Molecular Framework | Aliphatic homomonocyclic compounds |
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External Descriptors | - 5-[(1-carboxyethenyl)oxy]-6-hydroxycyclohexa-1,3-diene-1-carboxylic acid (CHEBI:17333 )
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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 | - Barker JL, Frost JW: Microbial synthesis of p-hydroxybenzoic acid from glucose. Biotechnol Bioeng. 2001 Dec;76(4):376-90. doi: 10.1002/bit.10160. [PubMed:11745165 ]
- Serrano M, Wang B, Aryal B, Garcion C, Abou-Mansour E, Heck S, Geisler M, Mauch F, Nawrath C, Metraux JP: Export of salicylic acid from the chloroplast requires the multidrug and toxin extrusion-like transporter EDS5. Plant Physiol. 2013 Aug;162(4):1815-21. doi: 10.1104/pp.113.218156. Epub 2013 Jun 11. [PubMed:23757404 ]
- Hill RK, Newkome GR: Stereochemistry of chorismic acid biosynthesis. J Am Chem Soc. 1969 Oct 8;91(21):5893-4. doi: 10.1021/ja01049a045. [PubMed:4897776 ]
- Gibson F: Chorismic acid: purification and some chemical and physical studies. Biochem J. 1964 Feb;90(2):256-61. doi: 10.1042/bj0900256. [PubMed:5834235 ]
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