Methylisocitric acid (PAMDB000674)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB000674
Identification
Name: Methylisocitric acid
Description:Methylisocitric 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
🔍MOLSDFPDBSMILESInChIView Structure
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
Average Molecular Weight: 206.1501
Monoisotopic Molecular Weight: 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
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.
Kingdom Organic compounds
Super ClassOrganic acids and derivatives
Class Carboxylic acids and derivatives
Sub ClassTricarboxylic acids and derivatives
Direct Parent Tricarboxylic acids and derivatives
Alternative Parents
Substituents
  • Tricarboxylic acid or derivatives
  • Beta-hydroxy acid
  • Hydroxy acid
  • Alpha-hydroxy acid
  • Tertiary alcohol
  • Carboxylic acid
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors Not Available
Physical Properties
State: Solid
Charge:-3
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility149.0 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity40.43 m3·mol-1ChemAxon
Polarizability17.37 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Cis-2-Methylaconitate + Water <> Methylisocitric acid
Methylisocitric acid <> Pyruvic acid + Succinic acid
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSNot Available
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