Record Information
Version2.0
Creation Date2012-05-31 14:08:14 -0600
Update Date2015-06-03 15:54:51 -0600
Secondary Accession Numbers
  • ECMDB06357
Identification
Name:Cis-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:
  • (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
Weight:Average: 188.1348
Monoisotopic: 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
Description belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassTricarboxylic 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
Physical Properties
State:Solid
Charge:-3
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility3.16 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity39.59 m³·mol⁻¹ChemAxon
Polarizability15.55 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Propanoate metabolismPW000940 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-002g-6900000000-ffb445dd87ee618648ffView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0079-9388000000-0ff4121be9b872f0c1abView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002e-4900000000-fe6584e3d383728ee001View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9200000000-80caf61386c108fcd0b4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-9100000000-327d1a78edc99f8fe760View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fi0-0900000000-734e75ff99c6e837cdcbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002b-9600000000-065cce37ffa797ab854cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006t-9000000000-925f178b16f34b5de908View in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
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

Enzymes

General function:
Involved in metabolic process
Specific function:
Citrate = isocitrate
Gene Name:
acnB
Uniprot ID:
P36683
Molecular weight:
93497
Reactions
Citrate = isocitrate.
(2S,3R)-3-hydroxybutane-1,2,3-tricarboxylate = (Z)-but-2-ene-1,2,3-tricarboxylate + H(2)O.
General function:
Involved in 2-methylcitrate dehydratase activity
Specific function:
Catalyzes the dehydration of 2-methylcitrate to 2- methyl-cis-aconitate. Also seems to be responsible for the residual aconitase activity of the acnAB-null strain
Gene Name:
prpD
Uniprot ID:
P77243
Molecular weight:
53951
Reactions
(2S,3S)-2-hydroxybutane-1,2,3-tricarboxylate = (Z)-but-2-ene-1,2,3-tricarboxylate + H(2)O.