Record Information |
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Version | 1.0 |
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Created at | 2020-11-23 19:39:26 UTC |
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Updated at | 2021-08-12 19:52:02 UTC |
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NP-MRD ID | NP0002748 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | trans-trans-Muconic acid |
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Provided By | BMRB |
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Description | Trans-trans-Muconic acid, also known as (2E,4E)-2,4-hexadienedioate or (e,e)-muconic acid, belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. Trans-trans-Muconic acid 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. It was first documented in 1999 (PMID: 10431356). Based on a literature review a significant number of articles have been published on trans-trans-Muconic acid (PMID: 17984079) (PMID: 16339183) (PMID: 14979410) (PMID: 12082012). |
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Structure | InChI=1S/C6H6O4/c7-5(8)3-1-2-4-6(9)10/h1-4H,(H,7,8)(H,9,10)/b3-1+,4-2+ |
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Synonyms | Value | Source |
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(2E,4E)-2,4-Hexadienedioic acid | ChEBI | (e,e)-2,4-Hexadienedioic acid | ChEBI | (e,e)-Muconic acid | ChEBI | trans,trans-1,3-Butadiene-1,4-dicarboxylic acid | ChEBI | trans,trans-2,4-Hexadienedioic acid | ChEBI | trans,trans-Buta-1,3-diene-1,4-dicarboxylic acid | ChEBI | (2E,4E)-2,4-Hexadienedioate | Generator | (e,e)-2,4-Hexadienedioate | Generator | (e,e)-Muconate | Generator | trans,trans-1,3-Butadiene-1,4-dicarboxylate | Generator | trans,trans-2,4-Hexadienedioate | Generator | trans,trans-Buta-1,3-diene-1,4-dicarboxylate | Generator | trans-trans-Muconate | Generator | 1,3-Butadiene-1,4-dicarboxylate | HMDB | 1,3-Butadiene-1,4-dicarboxylic acid | HMDB | Hexa-2,4-dienedioate | HMDB | Hexa-2,4-dienedioic acid | HMDB | Muconic acid | HMDB, MeSH | trans,trans-Muconic acid | HMDB | trans-beta-Hydromuconic acid | MeSH, HMDB | cis,cis-Muconate | MeSH, HMDB | Muconic acid, (e,e)-isomer | MeSH, HMDB |
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Chemical Formula | C6H6O4 |
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Average Mass | 142.1094 Da |
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Monoisotopic Mass | 142.02661 Da |
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IUPAC Name | (2E,4E)-hexa-2,4-dienedioic acid |
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Traditional Name | trans, trans-muconic acid |
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CAS Registry Number | Not Available |
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SMILES | OC(=O)\C=C\C=C\C(O)=O |
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InChI Identifier | InChI=1S/C6H6O4/c7-5(8)3-1-2-4-6(9)10/h1-4H,(H,7,8)(H,9,10)/b3-1+,4-2+ |
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InChI Key | TXXHDPDFNKHHGW-ZPUQHVIOSA-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, 500 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 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 medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Fatty Acyls |
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Sub Class | Fatty acids and conjugates |
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Direct Parent | Medium-chain fatty acids |
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Alternative Parents | |
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Substituents | - Medium-chain fatty acid
- Unsaturated fatty acid
- Dicarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic 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 ]
- Renner T, Baer-Koetzle M, Scherer G: Determination of sorbic acid in urine by gas chromatography-mass spectrometry. J Chromatogr A. 1999 Jun 25;847(1-2):127-33. doi: 10.1016/s0021-9673(98)01035-8. [PubMed:10431356 ]
- Kim S, Vermeulen R, Waidyanatha S, Johnson BA, Lan Q, Rothman N, Smith MT, Zhang L, Li G, Shen M, Yin S, Rappaport SM: Using urinary biomarkers to elucidate dose-related patterns of human benzene metabolism. Carcinogenesis. 2006 Apr;27(4):772-81. doi: 10.1093/carcin/bgi297. Epub 2005 Dec 8. [PubMed:16339183 ]
- Wiwanitkit V, Suwansaksri J, Soogarun S: The urine trans, trans muconic acid biomarker and platelet count in a sample of subjects with benzene exposure. Clin Appl Thromb Hemost. 2004 Jan;10(1):73-6. doi: 10.1177/107602960401000113. [PubMed:14979410 ]
- Hecht SS: Human urinary carcinogen metabolites: biomarkers for investigating tobacco and cancer. Carcinogenesis. 2002 Jun;23(6):907-22. doi: 10.1093/carcin/23.6.907. [PubMed:12082012 ]
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