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Bovine Metabolome Database



Showing metabocard for Fumaric acid (BMDB00134)

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 BMDB00134
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
SDF File Show
PDB File Show
2D Structure
3D Structure
Experimental PDB ID 1D4E Link Image
Experimental PDB File Show
Experimental PDB Structure
Experimental 1H NMR Spectrum Download Spectrum
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Experimental 13C NMR Spectrum Download Spectrum
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Experimental 13C HSQC Spectrum Download Spectrum
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Predicted 1H NMR Spectrum Show Image
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Predicted 13C NMR Spectrum Show Image
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Mass Spectrum
Low Energy
Download File
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Medium Energy
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High Energy
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Simplified TOCSY Spectrum Not Available
BMRB Spectrum Show Image
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Cellular Location
  • Cytoplasm (Predicted from LogP)
  • mitochondria
Biofluid Location
  • Breast_Milk
  • Rumen
Tissue Location Not Available
Concentrations (Normal)
Biofluid Breast_Milk
Value 2 - 81 uM
Age N/A
Sex N/A
Condition Normal
Comments Raw. skim.
References
Biofluid Breast_Milk
Value 23 +/- 6 uM
Age N/A
Sex N/A
Condition Normal
Comments Quantified by NMR in 2% milk
References
Biofluid Breast_Milk
Value 20 +/- 3 uM
Age N/A
Sex N/A
Condition Normal
Comments Quantified by NMR in skim milk
References
Biofluid Breast_Milk
Value 18 +/- 4 uM
Age N/A
Sex N/A
Condition Normal
Comments Quantified by NMR in 1% milk
References
Biofluid Breast_Milk
Value 16 +/- 4 uM
Age N/A
Sex N/A
Condition Normal
Comments Quantified by NMR in 3.25% milk
References
Biofluid Breast_Milk
Value NA NA
Age NA
Sex NA
Condition Normal
Comments Detected but not quantified in conventional whole milk
References
Biofluid Rumen
Value 8.75 +/- 3.84 uM
Age N/A
Sex N/A
Condition Normal
Comments Not Available
References
  • The rumen metabolome (in preparation)
Concentrations (Abnormal)
Biofluid Rumen
Value 11.66 +/- 3.43 uM
Age N/A
Sex N/A
Condition Rumen acidosis
Comments Not Available
References
  • The rumen metabolome (in preparation)
Pathway Names
  • Alanine and aspartate metabolism
  • Arginine and Proline Metabolism
  • Citrate Cycle
  • Nicotinate and Nicotinamide Metabolism
  • Tyrosine Metabolism
  • Urea Cycle and Metabolism of Amino Groups
HMDB Pathways
Name Alanine and aspartate metabolism
Image Show Link Image
Name Arginine and Proline Metabolism
Image Show Link Image
Name Citrate Cycle
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Name Nicotinate and Nicotinamide Metabolism
Image Show Link Image
Name Tyrosine Metabolism
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Name Urea Cycle and Metabolism of Amino Groups
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KEGG Pathways
Name Alanine and aspartate metabolism
Image Show Link Image
Name Arginine and Proline Metabolism
Image Show Link Image
Name Citrate Cycle
Image Show Link Image
Name Nicotinate and Nicotinamide Metabolism
Image Show Link Image
Name Tyrosine Metabolism
Image Show Link Image
Name Urea Cycle and Metabolism of Amino Groups
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SimCell Pathways
Name Alanine and aspartate metabolism
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Graph Show Link Image
SBML Download (XML) Link Image
Name Arginine and Proline Metabolism
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Graph
SBML
Name Citrate Cycle
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Graph Show Link Image
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Name Nicotinate and Nicotinamide Metabolism
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Graph Show Link Image
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Name Tyrosine Metabolism
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Graph
SBML
Name Urea Cycle and Metabolism of Amino Groups
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SBML Download (XML) Link Image
General References
  1. Wikipedia Link Image