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(R)-2,3-Dihydroxy-3-methylvalerate (YMDB00068)

Identification
YMDB IDYMDB00068
Name(R)-2,3-Dihydroxy-3-methylvalerate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description(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. Based on a literature review a small amount of articles have been published on (R)-2,3-Dihydroxy-3-methylvalerate.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
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 + hydron → NADP + (R)-2,3-Dihydroxy-3-methylvalerate
(R)-2,3-Dihydroxy-3-methylvalerate → water + (S)-3-methyl-2-oxovaleric acid
KEGG Reactions
(R)-2,3-Dihydroxy-3-methylvalerate → water + (S)-3-methyl-2-oxovaleric acid
NADPH + hydron + (S)-2-acetyl-2-hydroxybutanoate → NADP + (R)-2,3-Dihydroxy-3-methylvalerate
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-9000000000-d382043e81321879e92eJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00tb-9464000000-0280de9eaa4c12333997JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05aj-7900000000-ed4255c918254a1dc462JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0kar-9600000000-420faa83ea76001db2e9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pb9-9000000000-393b15b5811231e32693JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udj-2900000000-d582074beb8b89338fa5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9400000000-5ee3e425ebda8358d337JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05g0-9000000000-db72ead6bd87a129b325JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0h32-2900000000-0dc4c2a3c02313bed77cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9000000000-431db2e8dea59bdd5c38JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-349f8877717c1418480eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-81689c0553421abfcd88JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9100000000-d9815468ea9acf930e9eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9100000000-f894bf4ab44aaac79501JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
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

Protein Details
1. Ketol-acid reductoisomerase, mitochondrial
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.
Protein Details
2. Dihydroxy-acid dehydratase, mitochondrial
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.
Protein Details
3. 2-dehydropantoate 2-reductase
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.