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| Record Information |
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| Version | 1.0 |
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| Creation Date | 2016-09-30 22:20:01 UTC |
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| Update Date | 2020-06-04 20:50:59 UTC |
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| BMDB ID | BMDB0000134 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | Fumaric acid |
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| Description | Fumaric acid, also known as fumarate or E297, belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups. Fumaric acid exists as a solid, possibly soluble (in water), and a weakly acidic compound (based on its pKa) molecule. Fumaric acid exists in all living species, ranging from bacteria to humans. Fumaric acid is a potentially toxic compound. |
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| Structure | |
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| Synonyms | | Value | Source |
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| (2E)-2-Butenedioic acid | ChEBI | | (e)-2-Butenedioic acid | ChEBI | | e297 | ChEBI | | Fumarsaeure | ChEBI | | trans-1,2-Ethylenedicarboxylic acid | ChEBI | | trans-But-2-enedioic acid | ChEBI | | trans-Butenedioic acid | ChEBI | | (2E)-2-Butenedioate | Generator | | (e)-2-Butenedioate | Generator | | trans-1,2-Ethylenedicarboxylate | Generator | | trans-But-2-enedioate | Generator | | trans-Butenedioate | Generator | | Fumarate | Generator | | (2E)-But-2-enedioate | HMDB | | (2E)-But-2-enedioic acid | HMDB | | 2-(e)-Butenedioate | HMDB | | 2-(e)-Butenedioic acid | HMDB | | Allomaleate | HMDB | | Allomaleic acid | HMDB | | Boletate | HMDB | | Boletic acid | HMDB | | FC 33 | HMDB | | Lichenate | HMDB | | Lichenic acid | HMDB | | trans-2-Butenedioate | HMDB | | trans-2-Butenedioic acid | HMDB | | Furamag | HMDB | | Mafusol | HMDB | | Fumaric acid | HMDB |
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| Chemical Formula | C4H4O4 |
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| Average Molecular Weight | 116.0722 |
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| Monoisotopic Molecular Weight | 116.010958616 |
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| IUPAC Name | Not Available |
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| Traditional Name | Not Available |
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| CAS Registry Number | 110-17-8 |
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| SMILES | Not Available |
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| InChI Identifier | InChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1+ |
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| InChI Key | VZCYOOQTPOCHFL-OWOJBTEDSA-N |
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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 | - Fatty acyl
- Fatty acid
- Unsaturated fatty acid
- Dicarboxylic acid or derivatives
- Carboxylic acid
- 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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| Ontology |
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| Status | Detected and Quantified |
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| Origin | |
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| Biofunction | Not Available |
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| Application | Not Available |
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| Cellular locations | - Cell membrane
- Cytoplasm
- Membrane
- Mitochondria
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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 | 549 °C | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | 7.0 mg/mL | Not Available | | LogP | 0.46 | HANSCH,C ET AL. (1995) |
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| Predicted Properties | Not Available |
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| Spectra |
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| Spectra | |
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| Biological Properties |
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| Cellular Locations | - Cell membrane
- Cytoplasm
- Membrane
- Mitochondria
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| Biospecimen Locations | - Blood
- Colostrum
- Liver
- Longissimus Thoracis Muscle
- Mammary Gland
- Milk
- Muscle
- Placenta
- Prostate Tissue
- Ruminal Fluid
- Semen
- Semimembranosus Muscle
- Testis
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| Pathways | |
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| Normal Concentrations |
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| Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Blood | Detected and Quantified | 1.2 +/- 0.2 uM | Not Specified | Not Specified | Normal | | details | | Colostrum | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Liver | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Liver | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Liver | Detected and Quantified | 299 +/- 55 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Liver | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Longissimus Thoracis Muscle | Detected and Quantified | 141 +/- 64 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Mammary Gland | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Mammary Gland | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 11.63 +/- 3.65 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 2 - 81 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 7 - 23 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 10 - 23 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 13 +/- 1 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 13 +/- 1 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 13 +/- 1 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 14 +/- 1 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 11.20 +/- 4.36 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 12.54 +/- 2.98 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 36-208 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 107.37 +/- 14.42 uM | Not Specified | Not Specified | Normal | | details | | Muscle | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 123.02 +/- 19.31 uM | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 160.89 +/- 17.1 uM | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 73-178 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 140 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 84.76 +/- 11.89 uM | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 37-49 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Placenta | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Prostate Tissue | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 19-315 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 5.82 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 1.42 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 6.44 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 1.64 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 18 +/- 7 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 8.75 +/- 3.84 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 11.2 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 11.2 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 7.5 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 7.5 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 11.7 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 11.7 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 8.8 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 8.8 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 11 +/- 4 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 8 +/- 2 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 12 +/- 4 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 9 +/- 4 uM | Not Specified | Not Specified | Normal | | details | | Semen | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Semimembranosus Muscle | Detected and Quantified | 220 +/- 76 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Testis | Detected and Quantified | 27 +/- 8 nmol/g of tissue | Not Specified | Not Specified | Normal | | details |
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| Abnormal Concentrations |
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| Ruminal Fluid | Detected and Quantified | 11.66 +/- 3.43 uM | Not Specified | Not Specified | Rumen acidosis | | details |
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| External Links |
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| HMDB ID | HMDB0000134 |
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| DrugBank ID | DB01677 |
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| Phenol Explorer Compound ID | Not Available |
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| FooDB ID | FDB003291 |
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| KNApSAcK ID | C00001183 |
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| Chemspider ID | 10197150 |
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| KEGG Compound ID | C00122 |
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| BioCyc ID | FUM |
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| BiGG ID | 33938 |
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| Wikipedia Link | Fumaric_Acid |
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| METLIN ID | 3242 |
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| PubChem Compound | 444972 |
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| PDB ID | Not Available |
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| ChEBI ID | 18012 |
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| References |
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| Synthesis Reference | Dong, Changsheng; Ma, Xinming. Method for preparation of fumaric acid from the tail gas acid spray solution from oxidation of phthalic anhydride. Faming Zhuanli Shenqing Gongkai Shuomingshu (2007), 5pp. |
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| Material Safety Data Sheet (MSDS) | Not Available |
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| General References | - Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563. [PubMed:20338431 ]
- Klein MS, Buttchereit N, Miemczyk SP, Immervoll AK, Louis C, Wiedemann S, Junge W, Thaller G, Oefner PJ, Gronwald W: NMR metabolomic analysis of dairy cows reveals milk glycerophosphocholine to phosphocholine ratio as prognostic biomarker for risk of ketosis. J Proteome Res. 2012 Feb 3;11(2):1373-81. doi: 10.1021/pr201017n. Epub 2011 Dec 9. [PubMed:22098372 ]
- Sundekilde UK, Poulsen NA, Larsen LB, Bertram HC: Nuclear magnetic resonance metabonomics reveals strong association between milk metabolites and somatic cell count in bovine milk. J Dairy Sci. 2013 Jan;96(1):290-9. doi: 10.3168/jds.2012-5819. Epub 2012 Nov 22. [PubMed:23182357 ]
- Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30. [PubMed:25087032 ]
- Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15. [PubMed:23497994 ]
- Scano P, Murgia A, Pirisi FM, Caboni P: A gas chromatography-mass spectrometry-based metabolomic approach for the characterization of goat milk compared with cow milk. J Dairy Sci. 2014 Oct;97(10):6057-66. doi: 10.3168/jds.2014-8247. Epub 2014 Aug 6. [PubMed:25108860 ]
- Maher AD, Hayes B, Cocks B, Marett L, Wales WJ, Rochfort SJ: Latent biochemical relationships in the blood-milk metabolic axis of dairy cows revealed by statistical integration of 1H NMR spectroscopic data. J Proteome Res. 2013 Mar 1;12(3):1428-35. doi: 10.1021/pr301056q. Epub 2013 Feb 21. [PubMed:23394630 ]
- O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027. [PubMed:29642378 ]
- Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386. Metabolomics.
- A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.
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