You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2007-05-23 10:47:16 UTC
Update Date2019-07-23 05:47:22 UTC
HMDB IDHMDB0006471
Secondary Accession Numbers
  • HMDB06471
Metabolite Identification
Common NameMethylisocitric 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. Methylisocitric acid has also been found to be a metabolite of Candida (https://www.tandfonline.com/doi/pdf/10.1080/00021369.1974.10861293).
Structure
Data?1563860842
Synonyms
ValueSource
(2R,3S)2-MethylisocitrateHMDB
(2S,3R)-3-Hydroxybutane-1,2,3-tricarboxylateHMDB
3-Carboxy-2,3-dideoxy-4-C-methylpentaric acidHMDB
3-Hydroxy-1,2,3-butanetricarboxylateHMDB
3-Hydroxy-1,2,3-butanetricarboxylic acidHMDB
3-Hydroxybutane-1,2,3-tricarboxylic acidHMDB
alpha-MethylisocitrateHMDB
D.L-methylisocitrateHMDB
DL-Methylisocitric acidHMDB
DL-threo-alpha-MethylisocitrateHMDB
threo-alpha-MethylisocitrateHMDB
threo-alpha-Methylisocitrate, (3)H-labeledMeSH
Chemical FormulaC7H10O7
Average Molecular Weight206.1501
Monoisotopic Molecular Weight206.042652674
IUPAC Name1-hydroxy-1-methylpropane-1,2,3-tricarboxylic acid
Traditional Nameα-methylisocitric acid
CAS Registry NumberNot Available
SMILES
CC(O)(C(CC(O)=O)C(O)=O)C(O)=O
InChI Identifier
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)
InChI KeyHHKPKXCSHMJWCF-UHFFFAOYSA-N
Chemical 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.
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
Ontology
Disposition

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-9700000000-5e955ef633a08113ea4bJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-004i-6237900000-699512d84d6d00556b85JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000l-0900000000-f2ba7990914621684f43JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00xs-6900000000-56bcf049292c1d2aec9fJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01bc-5900000000-5450b7d1dc2e0d752d8fJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0909-2910000000-76e456521d06eb2df306JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-2900000000-9ff275785270b3b9744aJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9300000000-08a246451feb097e60eeJSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023929
KNApSAcK IDNot Available
Chemspider ID498
KEGG Compound IDC04593
BioCyc IDCPD-618
BiGG ID44122
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound513
PDB IDNot Available
ChEBI ID15607
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available