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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2009-04-06 16:19:53 UTC
Update Date2017-10-23 19:06:00 UTC
HMDB IDHMDB0012140
Secondary Accession Numbers
  • HMDB12140
Metabolite Identification
Common Name(R) 2,3-Dihydroxy-3-methylvalerate
Description(R) 2,3-Dihydroxy-methylvalerate is an intermediate in valine, leucine and isoleucine biosynthesis. The pathway of valine biosynthesis is a four-step pathway that shares all of its steps with the parallel pathway of isoleucine biosynthesis. These entwined pathways are part of the superpathway of leucine, valine, and isoleucine biosynthesis, that generates not only isoleucine and valine, but also leucine. (R) 2,3-Dihydroxy-methylvalerate is generated from 3-Hydroxy-3-methyl-2-oxopentanoic acid via the enzyme ketol-acid reductoisomerase (EC 1.1.1.86) then it is converted to (S)-3-methyl-2-oxopentanoic via the dihydroxy-acid dehydratase (EC:4.2.1.9).
Structure
Thumb
Synonyms
ValueSource
(2R,3R)-2,3-Dihydroxy-3-methylvaleric acidChEBI
(2R,3R)-2,3-Dihydroxy-3-methylvalerateGenerator
(R) 2,3-Dihydroxy-3-methylvaleric acidGenerator
(2R,3R)-2,3-Dihydroxy-3-methylpentanoateHMDB
(2R,3R)-2,3-Dihydroxy-3-methylpentanoic acidHMDB
(R)-2,3-Dihydroxy-3-methylpentanoateHMDB
(R)-2,3-Dihydroxy-3-methylpentanoic acidHMDB
(R)-2,3-Dihydroxy-3-methylvalerateHMDB
1-keto-2-MethylvalerateHMDB
2,3-Dihydroxy-3-methyl-valeric acidHMDB
2,3-Dihydroxy-3-methylpentanoateHMDB
2,3-Dihydroxy-3-methylpentanoic acidHMDB
2,3-Dihydroxy-valerianic acidHMDB
4,5-Dideoxy-3-C-methyl-pentonic acidHMDB
alpha,beta-Dihydroxy-beta-methylvaleric acidHMDB
CID8HMDB
DMVHMDB
Chemical FormulaC6H12O4
Average Molecular Weight148.1571
Monoisotopic Molecular Weight148.073558872
IUPAC Name(2R,3R)-2,3-dihydroxy-3-methylpentanoic acid
Traditional Name(2R,3R)-2,3-dihydroxy-3-methylpentanoic acid
CAS Registry Number562-43-6
SMILES
CC[C@@](C)(O)[C@@H](O)C(O)=O
InChI Identifier
InChI=1S/C6H12O4/c1-3-6(2,10)4(7)5(8)9/h4,7,10H,3H2,1-2H3,(H,8,9)/t4-,6+/m0/s1
InChI KeyPDGXJDXVGMHUIR-UJURSFKZSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassFatty Acyls
Direct ParentHydroxy fatty acids
Alternative Parents
Substituents
  • Branched fatty acid
  • Methyl-branched fatty acid
  • Short-chain hydroxy acid
  • Hydroxy fatty acid
  • Alpha-hydroxy acid
  • Hydroxy acid
  • Monosaccharide
  • Tertiary alcohol
  • 1,2-diol
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Source:

Route of exposure:

  Enteral:

Biological Location:

  Subcellular:

  Biofluid and excreta:

Role

Industrial application:

  Pharmaceutical industry:

Biological role:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

    Chemical reaction:

    Biochemical process:

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 Solubility486 g/LALOGPS
logP-0.44ALOGPS
logP-0.3ChemAxon
logS0.52ALOGPS
pKa (Strongest Acidic)3.93ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity33.96 m³·mol⁻¹ChemAxon
Polarizability14.43 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-9000000000-d382043e81321879e92eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00tb-9464000000-0280de9eaa4c12333997View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05aj-7900000000-ed4255c918254a1dc462View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0kar-9600000000-420faa83ea76001db2e9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pb9-9000000000-393b15b5811231e32693View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udj-2900000000-d582074beb8b89338fa5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9400000000-5ee3e425ebda8358d337View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05g0-9000000000-db72ead6bd87a129b325View in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB028798
KNApSAcK IDNot Available
Chemspider ID395044
KEGG Compound IDC06007
BioCyc ID1-KETO-2-METHYLVALERATE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound448154
PDB IDDMV
ChEBI ID27512
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.