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Bovine Metabolome Database



Showing metabocard for cis-Aconitic acid (BMDB00072)

Legend: metabolite field enzyme field

Version 1.0
Creation Date 2005-11-16 15:48:42
Update Date 2009-05-28 13:51:25
Accession Number BMDB00072
Common Name cis-Aconitic acid
Description An intermediate in the tricarboxylic acid cycle produced by the dehydration of citric acid. The enzyme aconitase (aconitate hydratase; EC 4.2.1.3) catalyses the stereo-specific isomerization of citrate to isocitrate via cis-aconitate in the tricarboxylic acid cycle
Synonyms
  1. (1Z)-1-Propene-1,2,3-tricarboxylate
  2. (1Z)-1-Propene-1,2,3-tricarboxylic acid
  3. (Z)-1-Propene-1,2,3-tricarboxylate
  4. (Z)-1-Propene-1,2,3-tricarboxylic acid
  5. (Z)-Aconitate
  6. (Z)-Aconitic acid
  7. 1-cis-2,3-Propenetricarboxylate
  8. 1-cis-2,3-Propenetricarboxylic acid
  9. 1-propene-1,2,3-tricarboxylate
  10. 1-propene-1,2,3-tricarboxylic acid
  11. cis-1-Propene-1,2,3-tricarboxylate
  12. cis-1-Propene-1,2,3-tricarboxylic acid
  13. cis-Aconate
  14. cis-Aconic acid
  15. cis-Aconitate
  16. cis-Aconitic acid
  17. cis-Oxaloacetate
  18. cis-Oxaloacetic acid
Chemical IUPAC Name (1Z)-1-Propene-1,2,3-tricarboxylic acid
Chemical Formula C6H6O6
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Organic acids
Class
  • Tricarboxylic Acids
Sub Class
  • Short chain tricarboxylic acids
Family
  • Mammalian_Metabolite
Species
  • carboxylic acid; alkene
Biofunction
  • Component of Glyoxylate and dicarboxylate metabolism
Application
Source
  • Endogenous
Average Molecular Weight 174.108
Monoisotopic Molecular Weight 174.016434
Isomeric SMILES OC(=O)CC(=CC(O)=O)C(O)=O
Canonical SMILES OC(=O)CC(=CC(O)=O)C(O)=O
KEGG Compound ID C00417 Link Image
BioCyc ID CIS-ACONITATE Link Image
BiGG ID Not Available
Wikipedia Link Not Available
METLIN ID 5130 Link Image
PubChem Compound 309 Link Image
PubChem Substance 3707 Link Image
ChEBI ID 32805 Link Image
CAS Registry Number 585-84-2
InChI Identifier InChI=1/C6H6O6/c7-4(8)1-3(6(11)12)2-5(9)10/h1H,2H2,(H,7,8)(H,9,10)(H,11,12)/b3-1-
Synthesis Reference Gutierrez, Eddie N.; Lamberti, Vincent. cis and trans Aconitic acids and their salts. U.S. (1978), 16 pp.
Melting Point (Experimental) 125 oC
Experimental Water Solubility 400.0 mg/mL [BEILSTEIN] Source: PhysProp
Predicted Water Solubility 6.72 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge -3
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity -0.41 [Predicted by ALOGPS]; -1.1 [Predicted by PubChem via XLOGP]; -0.14 [MEYLAN,WM & HOWARD,PH (1995)] Calculated using ALOGPS
Material Safety Data Sheet (MSDS)
MOL File Show
SDF File Show
PDB File Show
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Download Spectrum
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Experimental 13C NMR Spectrum Not Available
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
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Medium Energy
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High Energy
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Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Cytoplasm
Biofluid Location Not Available
Tissue Location Not Available
Concentrations (Normal)
Biofluid Breast_Milk
Value NA NA
Age NA
Sex NA
Condition Normal
Comments Detected but not quantified in conventional whole milk
References
Concentrations (Abnormal) Not Available
Pathway Names
  • Citrate Cycle
  • Glyoxylate and Dicarboxylate Metabolism
HMDB Pathways
Name Citrate Cycle
Image Show Link Image
Name Glyoxylate and Dicarboxylate Metabolism
Image Show Link Image
KEGG Pathways
Name Citrate Cycle
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Name Glyoxylate and Dicarboxylate Metabolism
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SimCell Pathways
Name Citrate Cycle
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Graph Show Link Image
SBML Download (XML) Link Image
Name Glyoxylate and Dicarboxylate Metabolism
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Graph
SBML
General References Not Available