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Bovine Rumen Metabolome Database



Showing metabocard for Fumaric acid (RMDB00134)

Legend: metabolite field enzyme field

Version 1.0
Creation Date 2005-11-16 15:48:42
Update Date 2009-07-02 15:05:42
Accession Number RMDB00134
Common Name Fumaric acid
Description A precursor to L-malate in the Krebs tricarboxylic acid cycle. It is formed by the oxidation of succinate by succinate dehydrogenase. Fumarate is converted by fumarase to malate. A fumarate is a salt or ester of the organic compound fumaric acid, a dicarboxylic acid. (wikipedia)
Synonyms
  1. (2E)-But-2-enedioate
  2. (2E)-But-2-enedioic acid
  3. (E)-2-Butenedioate
  4. (E)-2-Butenedioic acid
  5. 2-(E)-Butenedioate
  6. 2-(E)-Butenedioic acid
  7. Allomaleate
  8. Allomaleic acid
  9. Boletate
  10. Boletic acid
  11. FC 33
  12. Fumarate
  13. Fumaric acid
  14. Lichenate
  15. Lichenic acid
  16. trans-1,2-Ethylenedicarboxylate
  17. trans-1,2-Ethylenedicarboxylic acid
  18. trans-2-Butenedioate
  19. trans-2-Butenedioic acid
  20. trans-Butenedioate
  21. trans-Butenedioic acid
  22. sodium fumarate
Chemical IUPAC Name (E)-2-Butenedioic acid
Chemical Formula C4H4O4
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Organic acids
Class
  • Dicarboxylic Acids
Sub Class
  • Short chain dicarboxylic acids
Family
  • Mammalian_Metabolite
Species
  • carboxylic acid; alkene
Biofunction
Application
Source
  • Endogenous
Average Molecular Weight 116.072
Monoisotopic Molecular Weight 116.010956
Isomeric SMILES OC(=O)C=CC(O)=O
Canonical SMILES OC(=O)C=CC(O)=O
KEGG Compound ID C00122 Link Image
BioCyc ID FUM Link Image
BiGG ID 33938 Link Image
Wikipedia Link Fumaric acid Link Image
METLIN ID 3242 Link Image
PubChem Compound 723 Link Image
PubChem Substance 11452343 Link Image
ChEBI ID 29806 Link Image
CAS Registry Number 110-17-8
InChI Identifier InChI=1/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1+
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.
Melting Point (Experimental) 549 oC
Experimental Water Solubility 7.0 mg/mL [US EPA (1981)] Source: PhysProp
Predicted Water Solubility 24.1 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge -2
State Solid
Experimental LogP/Hydrophobicity 0.46 [HANSCH,C ET AL. (1995)] Source: PhysProp
Predicted LogP/Hydrophobicity 0.21 [Predicted by ALOGPS]; -0.4 [Predicted by PubChem via XLOGP] Calculated using ALOGPS
Material Safety Data Sheet (MSDS)
MOL File Show Link Image
SDF File Show Link Image
PDB File Show Link Image
2D Structure
3D Structure
Experimental PDB ID 1D4E Link Image
Experimental PDB File Show
Experimental PDB Structure
Experimental 1H NMR Spectrum Not Available
Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Not Available
Predicted 1H NMR Spectrum Show Image
Show Peaklist
Predicted 13C NMR Spectrum Show Image
Show Peaklist
Mass Spectrum
Low Energy
Download File
Show Experimental Conditions Link Image
Medium Energy
Download File
Show Experimental Conditions Link Image
High Energy
Download File
Show Experimental Conditions Link Image
Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Cytoplasm (Predicted from LogP)
  • mitochondria
Biofluid Location
  • Cow_Milk
  • Rumen
Tissue Location Not Available
Concentrations (Normal)
Biofluid Rumen
Value 8.75 +/- 3.84 uM
Age N/A
Sex N/A
Condition Normal
Breed Not Available
Experimental Condition Not Available
Comments Not Available
References
  • The rumen metabolome (in preparation)
Biofluid Rumen
Value 3.7 +/- 3.0 uM
Age N/A
Sex Female
Condition Normal
Breed Not Available
Experimental Condition Not Available
Comments Not Available
References
  • Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Burim N. Ametaj, Qendrim Zebeli, Fozia Saleem, Nikolaos Psychogios, Michael J. Lewis, Suzanna M. Dunn, Jianguo Xia and David S. Wishart Metabolomics 2010;6(4):583-594
Concentrations (Abnormal)
Biofluid Rumen
Value 11 +/- 4 uM
Age 4-5 years old
Sex Female (lactating)
Condition 15% barley grain in dry matter (DM) basis
Breed Holstein-Friesian
Experimental Condition Rumen fluid for the analysis was collected 15-20 minutes before the morning feeding on days 12 and 21 of each experimental period. Cows were fed once daily at 0800.
Comments Not Available
References
  • The rumen metabolome (in preparation)
Biofluid Rumen
Value 8 +/- 2 uM
Age 4-5 years old
Sex Female (lactating)
Condition 30% barley grain in dry matter (DM) basis
Breed Holstein-Friesian
Experimental Condition Rumen fluid for the analysis was collected 15-20 minutes before the morning feeding on days 12 and 21 of each experimental period. Cows were fed once daily at 0800.
Comments Not Available
References
  • The rumen metabolome (in preparation)
Biofluid Rumen
Value 12 +/- 4 uM
Age 4-5 years old
Sex Female (lactating)
Condition 45% barley grain in dry matter (DM) basis
Breed Holstein-Friesian
Experimental Condition Rumen fluid for the analysis was collected 15-20 minutes before the morning feeding on days 12 and 21 of each experimental period. Cows were fed once daily at 0800.
Comments Not Available
References
  • The rumen metabolome (in preparation)
Pathway Names Not Available
HMDB Pathways Not Available
KEGG Pathways Not Available
SimCell Pathways Not Available
General References
  1. Wikipedia Link Image