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Record Information
Version3.6
Creation Date2007-05-23 01:47:26 UTC
Update Date2017-03-02 21:28:09 UTC
HMDB IDHMDB06357
Secondary Accession NumbersNone
Metabolite Identification
Common Namecis-2-Methylaconitate
Descriptioncis-2-Methylaconitate is produced due to the dehydration of 2-methylcitrate in 2-methylcitric acid cycle. The cycle is catalyzed by a cofactor-less (PrpD) enzyme or by an aconitase-like (AcnD) enzyme. (PMID: 17567742 ).
Structure
Thumb
Synonyms
ValueSource
(Z)-But-2-ene-1,2,3-tricarboxylateChEBI
alpha-Methyl-cis-aconitateChEBI
alpha-MethylaconitateChEBI
cis-2-Butene-1,2,3-tricarboxylic acidChEBI
(Z)-But-2-ene-1,2,3-tricarboxylic acidGenerator
cis-2-Methylaconitic acidGenerator
a-Methyl-cis-aconitateGenerator
a-Methyl-cis-aconitic acidGenerator
alpha-Methyl-cis-aconitic acidGenerator
α-methyl-cis-aconitateGenerator
α-methyl-cis-aconitic acidGenerator
a-MethylaconitateGenerator
a-Methylaconitic acidGenerator
alpha-Methylaconitic acidGenerator
α-methylaconitateGenerator
α-methylaconitic acidGenerator
cis-2-Butene-1,2,3-tricarboxylateGenerator
(2Z)-But-2-ene-1,2,3-tricarboxylic acidHMDB
(Z)-2-Butene-1,2,3-tricarboxylic acidHMDB
Chemical FormulaC7H8O6
Average Molecular Weight188.1348
Monoisotopic Molecular Weight188.032087988
IUPAC Name(1Z)-1-methylprop-1-ene-1,2,3-tricarboxylic acid
Traditional Nameα-methylaconitate
CAS Registry Number6061-93-4
SMILES
C\C(C(O)=O)=C(/CC(O)=O)C(O)=O
InChI Identifier
InChI=1S/C7H8O6/c1-3(6(10)11)4(7(12)13)2-5(8)9/h2H2,1H3,(H,8,9)(H,10,11)(H,12,13)/b4-3-
InChI KeyNUZLRKBHOBPTQV-ARJAWSKDSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic acids and derivatives
Direct ParentTricarboxylic acids and derivatives
Alternative Parents
Substituents
  • Tricarboxylic acid or derivatives
  • Carboxylic acid
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Microbial
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility3.16 mg/mLALOGPS
logP-0.33ALOGPS
logP-0.13ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)2.25ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area111.9 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity39.59 m3·mol-1ChemAxon
Polarizability15.55 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-1900000000-202d4666a34f5b4f09f9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00fs-5900000000-9c256387d352a7a6ebb2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002b-9500000000-027a2750edf1831b7088View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000f-1900000000-e925a682247370a2fa7fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00mn-4900000000-ec6a931ab7e2e1653ea8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dj-9200000000-07d3197108036a4cb0ffView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023904
KNApSAcK IDNot Available
Chemspider ID2338376
KEGG Compound IDC04225
BioCyc IDCPD-1136
BiGG ID43396
Wikipedia LinkNot Available
NuGOwiki LinkHMDB06357
Metagene LinkHMDB06357
METLIN IDNot Available
PubChem Compound3080625
PDB IDNot Available
ChEBI ID16717
References
Synthesis ReferenceTabuchi, Takeshi; Uchiyama, Hiroo. Methylcitrate condensing and methylisocitrate cleaving enzymes. Evidence for the pathway of oxidation of propionyl-CoA to pyruvate via C7-tricarboxylic acids. Agricultural and Biological Chemistry (1975), 39(10), 2035-42.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Garvey GS, Rocco CJ, Escalante-Semerena JC, Rayment I: The three-dimensional crystal structure of the PrpF protein of Shewanella oneidensis complexed with trans-aconitate: insights into its biological function. Protein Sci. 2007 Jul;16(7):1274-84. Epub 2007 Jun 13. [PubMed:17567742 ]