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cis-2-Methylaconitate (YMDB00380)

Identification
YMDB IDYMDB00380
Namecis-2-Methylaconitate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Descriptioncis-2-Methylaconitate, also known as alpha-methylaconitate or a-methylaconitic acid, belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. cis-2-Methylaconitate exists in all living species, ranging from bacteria to plants to humans. Based on a literature review very few articles have been published on cis-2-Methylaconitate.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • (2Z)-but-2-ene-1,2,3-tricarboxylic acid
  • (Z)-2-Butene-1,2,3-tricarboxylic acid
  • (Z)-But-2-ene-1,2,3-tricarboxylate
  • Alpha-methyl-cis-aconitate
  • Alpha-methylaconitate
  • cis-2-Butene-1,2,3-tricarboxylic acid
  • (Z)-But-2-ene-1,2,3-tricarboxylic acid
  • a-Methyl-cis-aconitate
  • a-Methyl-cis-aconitic acid
  • alpha-Methyl-cis-aconitic acid
  • Α-methyl-cis-aconitate
  • Α-methyl-cis-aconitic acid
  • a-Methylaconitate
  • a-Methylaconitic acid
  • alpha-Methylaconitic acid
  • Α-methylaconitate
  • Α-methylaconitic acid
  • cis-2-Butene-1,2,3-tricarboxylate
  • cis-2-Methylaconitic acid
CAS number6061-93-4
WeightAverage: 188.1348
Monoisotopic: 188.032087988
InChI KeyNUZLRKBHOBPTQV-ARJAWSKDSA-N
InChIInChI=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-
IUPAC Name(1Z)-1-methylprop-1-ene-1,2,3-tricarboxylic acid
Traditional IUPAC Nameα-methylaconitate
Chemical FormulaC7H8O6
SMILES[H]OC(=O)C(=C(C(=O)O[H])C([H])([H])C(=O)O[H])C([H])([H])[H]
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
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
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 LocationsNot Available
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG Pathways
Propanoate metabolismec00640 Map00640
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-002g-6900000000-ffb445dd87ee618648ffJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0079-9388000000-0ff4121be9b872f0c1abJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-1900000000-202d4666a34f5b4f09f9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00fs-5900000000-9c256387d352a7a6ebb2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002b-9500000000-027a2750edf1831b7088JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000f-1900000000-e925a682247370a2fa7fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00mn-4900000000-ec6a931ab7e2e1653ea8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dj-9200000000-07d3197108036a4cb0ffJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002e-4900000000-fe6584e3d383728ee001JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9200000000-80caf61386c108fcd0b4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-9100000000-327d1a78edc99f8fe760JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fi0-0900000000-734e75ff99c6e837cdcbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002b-9600000000-065cce37ffa797ab854cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006t-9000000000-925f178b16f34b5de908JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
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),
External Links:
ResourceLink
CHEBI ID16717
HMDB IDHMDB06357
Pubchem Compound ID3080625
Kegg IDC04225
ChemSpider ID2338376
FOODB IDFDB023904
Wikipedia IDNot Available
BioCyc IDCPD-1136

Enzymes

Protein Details
1. Probable 2-methylcitrate dehydratase
General function:
Involved in 2-methylcitrate dehydratase activity
Specific function:
Catalyzes the dehydration of 2-methylcitrate to 2- methyl-cis-aconitate
Gene Name:
PDH1
Uniprot ID:
Q12428
Molecular weight:
57683.10156
Reactions
(2S,3S)-2-hydroxybutane-1,2,3-tricarboxylate → (Z)-but-2-ene-1,2,3-tricarboxylate + H(2)O.