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Identification
YMDB IDYMDB00068
Name(R)-2,3-Dihydroxy-3-methylvalerate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description(R) 2,3-Dihydroxy-3-methylvalerate, also known as (2R,3R)-(r) 2,3-dihydroxy-3-methylvalerate or (r) 2,3-dihydroxy-3-methylvalerate, belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group (R) 2,3-Dihydroxy-3-methylvalerate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
Synonyms
  • (2R,3R)-2,3-dihydroxy-3-methylpentanoate
  • (2R,3R)-2,3-dihydroxy-3-methylpentanoic acid
  • (2R,3R)-2,3-dihydroxy-3-methylvalerate
  • (R)-2,3-Dihydroxy-3-methylpentanoate
  • (R)-2,3-Dihydroxy-3-methylpentanoic acid
  • (R)-2,3-Dihydroxy-3-methylvalerate
  • 1-keto-2-methylvalerate
  • 2,3-Dihydroxy-3-Methyl-Valeric acid
  • 2,3-Dihydroxy-3-methylpentanoate
  • 2,3-Dihydroxy-3-methylpentanoic acid
  • 2,3-Dihydroxy-Valerianic acid
  • 4,5-dideoxy-3-C-methyl-pentonic acid
  • Alpha,beta-dihydroxy-beta-methylvaleric acid
  • CID8
  • DMV
  • (2R,3R)-2,3-Dihydroxy-3-methylvaleric acid
  • (R)-2,3-Dihydroxy-3-methylvaleric acid
  • (R) 2,3-Dihydroxy-3-methylvaleric acid
CAS number562-43-6
WeightAverage: 148.1571
Monoisotopic: 148.073558872
InChI KeyPDGXJDXVGMHUIR-UJURSFKZSA-N
InChIInChI=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
IUPAC Name(2R,3R)-2,3-dihydroxy-3-methylpentanoic acid
Traditional IUPAC Name(2R,3R)-2,3-dihydroxy-3-methylpentanoic acid
Chemical FormulaC6H12O4
SMILES[H]OC(=O)[C@]([H])(O[H])[C@@](O[H])(C([H])([H])[H])C([H])([H])C([H])([H])[H]
Chemical Taxonomy
Description belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
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
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
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
Biological Properties
Cellular Locations
  • Mitochondrion
Organoleptic PropertiesNot Available
SMPDB Pathways
isoleucine biosynthesisPW002476 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Valine, leucine and isoleucine biosynthesisec00290 Map00290
SMPDB Reactions
(S)-2-Aceto-2-hydroxybutanoic acid + NADPH + hydronNADP + (R)-2,3-Dihydroxy-3-methylvalerate
(R)-2,3-Dihydroxy-3-methylvaleratewater + (S)-3-methyl-2-oxovaleric acid
KEGG Reactions
(R)-2,3-Dihydroxy-3-methylvaleratewater + (S)-3-methyl-2-oxovaleric acid
NADPH + hydron + (S)-2-acetyl-2-hydroxybutanoateNADP + (R)-2,3-Dihydroxy-3-methylvalerate
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Ryan, E. D., Kohlhaw, G. B. (1974). "Subcellular localization of isoleucine-valine biosynthetic enzymes in yeast." J Bacteriol 120:631-637.4616942
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID27512
HMDB IDHMDB12140
Pubchem Compound ID448154
Kegg IDC06007
ChemSpider ID395044
FOODB IDFDB028798
Wikipedia IDNot Available
BioCyc ID1-KETO-2-METHYLVALERATE

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
(R)-2,3-dihydroxy-3-methylbutanoate + NADP(+) = (S)-2-hydroxy-2-methyl-3-oxobutanoate + NADPH
Gene Name:
ILV5
Uniprot ID:
P06168
Molecular weight:
44368.10156
Reactions
(R)-2,3-dihydroxy-3-methylbutanoate + NADP(+) → (S)-2-hydroxy-2-methyl-3-oxobutanoate + NADPH.
(2R,3R)-2,3-dihydroxy-3-methylpentanoate + NADP(+) → (S)-2-hydroxy-2-ethyl-3-oxobutanoate + NADPH.
General function:
Involved in metabolic process
Specific function:
2,3-dihydroxy-3-methylbutanoate = 3-methyl-2- oxobutanoate + H(2)O
Gene Name:
ILV3
Uniprot ID:
P39522
Molecular weight:
62860.60156
Reactions
2,3-dihydroxy-3-methylbutanoate → 3-methyl-2-oxobutanoate + H(2)O.
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the NADPH-dependent reduction of ketopantoate into pantoic acid
Gene Name:
PAN5
Uniprot ID:
P38787
Molecular weight:
42820.89844
Reactions
(R)-pantoate + NADP(+) → 2-dehydropantoate + NADPH.