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Methylisocitric acid (YMDB00094)

Identification
YMDB IDYMDB00094
NameMethylisocitric acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionMethylisocitric acid, also known as alpha-methylisocitrate, belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. Methylisocitric acid exists in all living species, ranging from bacteria to plants to humans. Based on a literature review very few articles have been published on Methylisocitric acid.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
  • (2R,3S)2-methylisocitrate
  • (2S,3R)-3-Hydroxybutane-1,2,3-tricarboxylate
  • 3-Carboxy-2,3-dideoxy-4-C-methylpentaric acid
  • 3-Hydroxy-1,2,3-butanetricarboxylate
  • 3-hydroxy-1,2,3-Butanetricarboxylic acid
  • 3-hydroxybutane-1,2,3-tricarboxylic acid
  • Alpha-methylisocitrate
  • D.L-methylisocitrate
  • DL-Methylisocitric acid
  • DL-threo-alpha-methylisocitrate
  • Methylisocitric acid
  • Threo-alpha-methylisocitrate
  • alpha-Methylisocitric acid
  • 3-Carboxy-2,3-dideoxy-4-C-methylpentarate
  • a-Methylisocitrate
  • a-Methylisocitric acid
  • Α-methylisocitrate
  • Α-methylisocitric acid
  • Methylisocitrate
  • Threo-alpha-methylisocitrate, (3)H-labeled
CAS number20298-95-7
WeightAverage: 206.1501
Monoisotopic: 206.042652674
InChI KeyHHKPKXCSHMJWCF-UHFFFAOYSA-N
InChIInChI=1S/C7H10O7/c1-7(14,6(12)13)3(5(10)11)2-4(8)9/h3,14H,2H2,1H3,(H,8,9)(H,10,11)(H,12,13)
IUPAC Name1-hydroxy-1-methylpropane-1,2,3-tricarboxylic acid
Traditional IUPAC Nameα-methylisocitric acid
Chemical FormulaC7H10O7
SMILES[H]OC(=O)C([H])([H])C([H])(C(=O)O[H])C(O[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
  • Hydroxy acid
  • Alpha-hydroxy acid
  • Tertiary alcohol
  • Carboxylic acid
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility149 g/LALOGPS
logP-0.87ALOGPS
logP-1ChemAxon
logS-0.14ALOGPS
pKa (Strongest Acidic)3.17ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area132.13 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity40.43 m³·mol⁻¹ChemAxon
Polarizability17.37 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • mitochondrion
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG Pathways
Propanoate metabolismec00640 Map00640
SMPDB ReactionsNot Available
KEGG Reactions
(2S,3S)-2-Methylcitric acid ↔ Methylisocitric acid
Methylisocitric acid → Pyruvic acid + Succinic acid
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-9700000000-5e955ef633a08113ea4bJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-004i-6237900000-699512d84d6d00556b85JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000l-0900000000-f2ba7990914621684f43JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00xs-6900000000-56bcf049292c1d2aec9fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01bc-5900000000-5450b7d1dc2e0d752d8fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0909-2910000000-76e456521d06eb2df306JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-2900000000-9ff275785270b3b9744aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9300000000-08a246451feb097e60eeJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-1f979af8cdefad8b7fc2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0900000000-72ddc9d43332ef4d4c1eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014l-7900000000-b552ff6cfa53a6d1478cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000j-0910000000-69d3ffec30c69b150998JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fxy-2900000000-cfe61511f4feda222931JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9100000000-7f3760d40cf2db6bf9ebJSpectraViewer
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
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Luttik, M. A., Kotter, P., Salomons, F. A., van der Klei, I. J., van Dijken, J. P., Pronk, J. T. (2000). "The Saccharomyces cerevisiae ICL2 gene encodes a mitochondrial 2-methylisocitrate lyase involved in propionyl-coenzyme A metabolism." J Bacteriol 182:7007-7013.11092862
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID15607
HMDB IDHMDB06471
Pubchem Compound ID513
Kegg IDC04593
ChemSpider ID498
FOODB IDFDB023929
Wikipedia IDNot Available
BioCyc IDCPD-618

Enzymes

Protein Details
1. Mitochondrial 2-methylisocitrate lyase
General function:
Involved in isocitrate lyase activity
Specific function:
Catalyzes the formation of pyruvate and succinate from 2-methylisocitrate during the metabolism of endogenous propionyl- CoA. Does not act on isocitrate
Gene Name:
ICL2
Uniprot ID:
Q12031
Molecular weight:
64975.39844
Reactions
(2S,3R)-3-hydroxybutane-1,2,3-tricarboxylate → pyruvate + succinate.