Record Information
Version2.0
Creation Date2012-05-31 14:08:34 -0600
Update Date2015-06-03 15:54:52 -0600
Secondary Accession Numbers
  • ECMDB06471
Identification
Name:Methylisocitric acid
DescriptionMethylisocitric acid is a product of bacterial metabolism in the gut. It can be produced by 2-methylisocitrate lyase and by 2-methylisocitrate dehydratase.
Structure
Thumb
Synonyms:
  • (2R,3S)2-methylisocitrate
  • (2R,3S)2-methylisocitric acid
  • (2S,3R)-3-Hydroxybutane-1,2,3-tricarboxylate
  • (2S,3R)-3-Hydroxybutane-1,2,3-tricarboxylic acid
  • 3-Carboxy-2,3-dideoxy-4-C-methylpentarate
  • 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-tricarboxylate
  • 3-Hydroxybutane-1,2,3-tricarboxylic acid
  • threo-Ds-2-methylisocitrate
  • a-Methylisocitrate
  • a-Methylisocitric acid
  • Alpha-Methylisocitrate
  • Alpha-Methylisocitric acid
  • D.L-Methylisocitrate
  • D.L-Methylisocitric acid
  • DL-Methylisocitrate
  • DL-Methylisocitric acid
  • DL-threo-a-Methylisocitrate
  • DL-threo-a-Methylisocitric acid
  • DL-threo-alpha-methylisocitrate
  • DL-threo-alpha-methylisocitric acid
  • DL-threo-α-Methylisocitrate
  • DL-threo-α-Methylisocitric acid
  • Methylisocitrate
  • Methylisocitric acid
  • threo-a-Methylisocitrate
  • threo-a-Methylisocitric acid
  • Threo-alpha-methylisocitrate
  • Threo-alpha-methylisocitric acid
  • Threo-Ds-2-methylisocitrate
  • Threo-Ds-2-methylisocitric acid
  • threo-α-Methylisocitrate
  • threo-α-Methylisocitric acid
  • α-Methylisocitrate
  • α-Methylisocitric acid
Chemical Formula:C7H10O7
Weight:Average: 206.1501
Monoisotopic: 206.042652674
InChI Key:HHKPKXCSHMJWCF-UHFFFAOYSA-N
InChI:InChI=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)
CAS number:Not Available
IUPAC Name:1-hydroxy-1-methylpropane-1,2,3-tricarboxylic acid
Traditional IUPAC Name:α-methylisocitric acid
SMILES:CC(O)(C(CC(O)=O)C(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 DescriptorsNot Available
Physical Properties
State:Solid
Charge:-3
Melting point:Not Available
Experimental Properties:
PropertyValueSource
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: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, Positivesplash10-000i-9700000000-5e955ef633a08113ea4bView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-004i-6237900000-699512d84d6d00556b85View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000l-0900000000-f2ba7990914621684f43View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00xs-6900000000-56bcf049292c1d2aec9fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01bc-5900000000-5450b7d1dc2e0d752d8fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0909-2910000000-76e456521d06eb2df306View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-2900000000-9ff275785270b3b9744aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9300000000-08a246451feb097e60eeView in MoNA
References
References:
  • 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
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID15607
HMDB IDHMDB06471
Pubchem Compound ID513
Kegg IDC04593
ChemSpider ID498
Wikipedia IDNot Available
BioCyc IDCPD-618
EcoCyc IDCPD-618

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 catalytic activity
Specific function:
Catalyzes the formation of pyruvate and succinate from 2-methylisocitrate
Gene Name:
prpB
Uniprot ID:
P77541
Molecular weight:
32134
Reactions
(2S,3R)-3-hydroxybutane-1,2,3-tricarboxylate = pyruvate + succinate.