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Identification
YMDB IDYMDB00978
Name(2S,3S)-2-Methylcitric acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description(2S,3S)-2-hydroxybutane-1,2,3-tricarboxylate belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups (2S,3S)-2-hydroxybutane-1,2,3-tricarboxylate is an extremely weak basic (essentially neutral) compound (based on its pKa) (2S,3S)-2-hydroxybutane-1,2,3-tricarboxylate exists in both E. coli (prokaryote) and yeast (eukaryote).
Structure
Thumb
Synonyms
  • (2S,3S)-2-methylcitrate
  • 2-hydroxy-1,2,3-butanetricarboxylic acid
  • 2-hydroxybutane-1,2,3-tricarboxylate
  • 2-hydroxybutane-1,2,3-tricarboxylic acid
  • 2-methylcitrate
  • 2-methylcitric acid
  • (2S,3S)-2-Hydroxybutane-1,2,3-tricarboxylic acid
  • Methylcitric acid
  • 3-Carboxy-3-hydroxy-2-methylpentanedioic acid
  • 2-Methylcitric acid, 3H-labeled
CAS number6061-96-7
WeightAverage: 206.1501
Monoisotopic: 206.042652674
InChI KeyYNOXCRMFGMSKIJ-NFNCENRGSA-N
InChIInChI=1S/C7H10O7/c1-3(5(10)11)7(14,6(12)13)2-4(8)9/h3,14H,2H2,1H3,(H,8,9)(H,10,11)(H,12,13)/t3-,7+/m1/s1
IUPAC Name(1S,2S)-2-hydroxy-1-methylpropane-1,2,3-tricarboxylic acid
Traditional IUPAC Name(2S,3S)-2-methylcitric acid
Chemical FormulaC7H10O7
SMILESC[C@H](C(O)=O)[C@@](O)(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
  • 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 Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility175 g/LALOGPS
logP-0.89ALOGPS
logP-0.78ChemAxon
logS-0.07ALOGPS
pKa (Strongest Acidic)3.18ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area132.13 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity40.2 m³·mol⁻¹ChemAxon
Polarizability17.33 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 PathwaysNot Available
SMPDB ReactionsNot Available
KEGG Reactions
propionyl-CoA + water + Oxalacetic acid(2S,3S)-2-Methylcitric acid + hydron + Coenzyme A
(2S,3S)-2-Methylcitric acidMethylisocitric acid
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fer-4900000000-66b99961c9a1426fcc9eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-be0da5c29220e9e50325JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05i0-9600000000-2bead66ba2514df6497fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-1093-7900000000-e7a5530b8562d859e032JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0900-1910000000-0a84eb8e0df2e6eb450dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-07vi-4900000000-e89ea7de4d7e433cae1eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9300000000-c68ffdf8bf6f5380005eJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Pronk, J. T., van der Linden-Beuman, A., Verduyn, C., Scheffers, W. A., van Dijken, J. P. (1994). "Propionate metabolism in Saccharomyces cerevisiae: implications for the metabolon hypothesis." Microbiology 140 ( Pt 4):717-722.7912143
  • Gerike, U., Hough, D. W., Russell, N. J., Dyall-Smith, M. L., Danson, M. J. (1998). "Citrate synthase and 2-methylcitrate synthase: structural, functional and evolutionary relationships." Microbiology 144 ( Pt 4):929-935.9579066
  • Singh, J., Kumar, D., Ramakrishnan, N., Singhal, V., Jervis, J., Garst, J. F., Slaughter, S. M., DeSantis, A. M., Potts, M., Helm, R. F. (2005). "Transcriptional response of Saccharomyces cerevisiae to desiccation and rehydration." Appl Environ Microbiol 71:8752-8763.16332871
Synthesis Reference:Ewering, Christian; Braemer, Christian Oliver; Steinbuechel, Alexander. Production of 2-methylcitric acid by a recombinant Ralstonia eutropha strain. PCT Int. Appl. (2007), 30pp. CODEN: PIXXD2 WO 2007101866 A2 20070913 CAN 147:363646 AN 20
External Links:
ResourceLink
CHEBI ID50948
HMDB IDHMDB00379
Pubchem Compound ID515
Kegg IDNot Available
ChemSpider ID24534242
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

General function:
Involved in transferase activity, transferring acyl groups, acyl groups converted into alkyl on transfer
Specific function:
Acetyl-CoA + H(2)O + oxaloacetate = citrate + CoA
Gene Name:
CIT3
Uniprot ID:
P43635
Molecular weight:
53810.69922
Reactions
Acetyl-CoA + H(2)O + oxaloacetate → citrate + CoA.
propanoyl-CoA + H2O + oxaloacetate → (2R,3S)-2-hydroxybutane-1,2,3-tricarboxylate + CoA
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.