(2R,3S)-2-Hydroxybutane-1,2,3-tricarboxylate (PAMDB003442)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB003442
Identification
Name: (2R,3S)-2-Hydroxybutane-1,2,3-tricarboxylate
Description:(2R,3S)-2-Hydroxybutane-1,2,3-tricarboxylate is an intermediate in methylcitrate metabolism. It is involved in the reaction propinoyl-CoA + H2O + oxaloacetate = (2R,3S)-2-hydroxybutane-1,2,3-tricarboxylate + CoA which is mediated by the enzyme: 2-methylcitrate synthase.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • (2R,3S)-2-hydroxybutane-1,2,3-tricarboxylic acid
  • 2-Hydroxybutane-1,2,3-tricarboxylate
  • 2-Hydroxybutane-1,2,3-tricarboxylic acid
  • 2-Methylcitrate
  • 2-Methylcitric acid
  • 3-C-Carboxy-2,4-dideoxy-2-methyl-D-threo-pentarate
  • 3-C-Carboxy-2,4-dideoxy-2-methyl-D-threo-pentaric acid
Chemical Formula: C7H10O7
Average Molecular Weight: 206.1501
Monoisotopic Molecular Weight: 206.042652674
InChI Key: YNOXCRMFGMSKIJ-WVBDSBKLSA-N
InChI:InChI=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
CAS number: Not Available
IUPAC Name:(1S,2R)-2-hydroxy-1-methylpropane-1,2,3-tricarboxylic acid
Traditional IUPAC Name: (2R,3S)-2-methylcitric acid
SMILES:[H][C@@](C)(C(O)=O)[C@](O)(CC(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
Physical Properties
State: Not Available
Charge:-3
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility175.0 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity40.2 m3·mol-1ChemAxon
Polarizability17.3 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Pathways: Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-be0da5c29220e9e50325View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05i0-9600000000-2bead66ba2514df6497fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-1093-7900000000-e7a5530b8562d859e032View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0900-1910000000-0a84eb8e0df2e6eb450dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-07vi-4900000000-e89ea7de4d7e433cae1eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9300000000-c68ffdf8bf6f5380005eView in MoNA
References
References: Not Available
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI ID30836
HMDB IDNot Available
Pubchem Compound ID439681
Kegg IDC02225
ChemSpider ID388748
Wikipedia IDNot Available
BioCyc IDNot Available