cis-2-methylaconitate (PAMDB120023)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB120023
Identification
Name: cis-2-methylaconitate
Description:Tricarboxylate anion of (2Z)-but-2-ene-1,2,3-tricarboxylic acid; major species at pH 7.3.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • (1Z)-1-methylprop-1-ene-1,2,3-tricarboxylate
  • 2-methyl-cis-aconitate
Chemical Formula: C7H5O6
Average Molecular Weight: 185.113
Monoisotopic Molecular Weight: 188.03209
InChI Key: NUZLRKBHOBPTQV-ARJAWSKDSA-K
InChI: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)/p-3/b4-3-
CAS number: 6061-93-4
IUPAC Name:(2Z)-but-2-ene-1,2,3-tricarboxylate
Traditional IUPAC Name: ?-methylaconitate
SMILES:CC(=C(CC([O-])=O)C([O-])=O)C([O-])=O
Chemical Taxonomy
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.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Organic acids and derivatives
Sub ClassCarboxylic acids and derivatives
Direct Parent Tricarboxylic 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 Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-3
Melting point: Not Available
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
Biological Properties
Cellular Locations: Not Available
Reactions:
(2S,3S)-2-methylcitrate → cis-2-methylaconitate + Water
(2R,3S)-2-methylisocitrate → cis-2-methylaconitate + Water
Pathways:
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
References
References:
  • 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. [17567742 ]
Synthesis Reference: Tabuchi, 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
External Links:
ResourceLink
METABOLIGHTSMTBLC57872
HMDBHMDB06357
BIGG43396
CHEMSPIDER19951219
CHEBI57872
PUBCHEM23615274
CAS99-98-9
LIGAND-CPDC04225