Cis-2-Methylaconitate (PAMDB000668)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB000668
Identification
Name: Cis-2-Methylaconitate
Description:cis-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.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • (2Z)-but-2-ene-1,2,3-tricarboxylate
  • (2Z)-but-2-ene-1,2,3-tricarboxylic acid
  • (Z)-2-Butene-1,2,3-tricarboxylate
  • (Z)-2-Butene-1,2,3-tricarboxylic acid
  • (Z)-But-2-ene-1,2,3-tricarboxylate
  • (Z)-But-2-ene-1,2,3-tricarboxylic acid
  • 2-methyl-cis-aconitate
  • 2-Methyl-cis-aconitate
  • 2-Methyl-cis-aconitic acid
  • 2-methylaconitate
  • 2-Methylaconitic acid
  • a-Methyl-cis-aconitate
  • a-Methyl-cis-aconitic acid
  • a-Methylaconitate
  • a-Methylaconitic acid
  • Alpha-Methyl-cis-aconitate
  • Alpha-Methyl-cis-aconitic acid
  • Alpha-Methylaconitate
  • Alpha-Methylaconitic acid
  • Cis-2-Butene-1,2,3-tricarboxylate
  • Cis-2-Butene-1,2,3-tricarboxylic acid
  • Cis-2-Methylaconitic acid
  • α-Methyl-cis-aconitate
  • α-Methyl-cis-aconitic acid
  • α-Methylaconitate
  • α-Methylaconitic acid
Chemical Formula: C7H8O6
Average Molecular Weight: 188.1348
Monoisotopic Molecular Weight: 188.032087988
InChI Key: NUZLRKBHOBPTQV-ARJAWSKDSA-N
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)/b4-3-
CAS number: 6061-93-4
IUPAC Name:(1Z)-1-methylprop-1-ene-1,2,3-tricarboxylic acid
Traditional IUPAC Name: α-methylaconitate
SMILES:C\C(C(O)=O)=C(/CC(O)=O)C(O)=O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.
Kingdom Organic compounds
Super ClassOrganic acids and derivatives
Class Carboxylic acids and derivatives
Sub ClassTricarboxylic acids and derivatives
Direct Parent Tricarboxylic acids and derivatives
Alternative Parents
Substituents
  • Tricarboxylic acid or derivatives
  • Carboxylic acid
  • 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:
PropertyValueSource
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: Cytoplasm
Reactions:
Cis-2-Methylaconitate + Water <> Methylisocitric acid
Methylcitric acid + (2S,3S)-2-hydroxybutane-1,2,3-tricarboxylate <> Cis-2-Methylaconitate + Water
Methylcitric acid <> Cis-2-Methylaconitate + Water
(2S,3S)-2-hydroxybutane-1,2,3-tricarboxylate > Cis-2-Methylaconitate + Water
2-Methylcitric acid + Methylcitric acid > Water + Cis-2-Methylaconitate
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-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, G. S., Rocco, C. J., Escalante-Semerena, J. C., Rayment, I. (2007). "The three-dimensional crystal structure of the PrpF protein of Shewanella oneidensis complexed with trans-aconitate: insights into its biological function." Protein Sci 16:1274-1284. Pubmed: 17567742
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
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),
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI ID16717
HMDB IDHMDB06357
Pubchem Compound ID3080625
Kegg IDC04225
ChemSpider ID2338376
Wikipedia IDNot Available
BioCyc IDCPD-1136
EcoCyc IDCPD-1136