(R)-2,3-Dihydroxy-isovalerate (YMDB00063)

Identification
YMDB IDYMDB00063
Name(R)-2,3-Dihydroxy-isovalerate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description(R)-2,3-Dihydroxy-isovalerate 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-isovalerate.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
  • (2R)-2,3-dihydroxy-3-methylbutanoate
  • (2R)-2,3-dihydroxy-3-methylbutanoic acid
  • (R)-2,3-dihydroxy-3-methylbutanoate
  • (R)-2,3-dihydroxy-3-methylbutanoic acid
  • (R)-2,3-Dihydroxy-isovalerate
  • (R)-2,3-Dihydroxy-isovaleric acid
  • (R)-(-)-alpha,beta-Dihydroxyisovaleric acid
  • (R)-(-)-α,β-Dihydroxyisovaleric acid
CAS numberNot Available
WeightAverage: 134.1305
Monoisotopic: 134.057908808
InChI KeyJTEYKUFKXGDTEU-VKHMYHEASA-N
InChIInChI=1S/C5H10O4/c1-5(2,9)3(6)4(7)8/h3,6,9H,1-2H3,(H,7,8)/t3-/m0/s1
IUPAC Name(2R)-2,3-dihydroxy-3-methylbutanoic acid
Traditional IUPAC Name(R)-2,3-dihydroxy-isovalerate
Chemical FormulaC5H10O4
SMILESCC(C)(O)[C@@H](O)C(O)=O
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 Solubility529 g/LALOGPS
logP-0.83ALOGPS
logP-0.82ChemAxon
logS0.6ALOGPS
pKa (Strongest Acidic)3.8ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity29.44 m³·mol⁻¹ChemAxon
Polarizability12.48 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
Valine BiosynthesisPW002474 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Valine, leucine and isoleucine biosynthesisec00290 Map00290
SMPDB Reactions
(S)-2-Acetolactate + hydron + NADPH → NADP + (R)-2,3-Dihydroxy-isovalerate
(R)-2,3-Dihydroxy-isovalerate → water + 3-Methylbutanoic acid
KEGG Reactions
NADPH + hydron + 2-Acetolactate → NADP + (R)-2,3-Dihydroxy-isovalerate
(R)-2,3-Dihydroxy-isovalerate → Alpha-Ketoisovaleric acid + water
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9000000000-59e6990530d950227520JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00s9-9473000000-9708bfc20ee5ae043678JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-4900000000-196ffbbf313a33f24f27JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00ri-9300000000-aebebbbe2c7c11465a67JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-92af6a04d8cb7601ab35JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0019-9500000000-2837622949a6bd688094JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00s9-9400000000-0fc7aa81197fc5feb444JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dr-9000000000-45f3b95b2f30ea8445c1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-2900000000-fab4ee9aeca7067a9207JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-9100000000-b3da44872fd12f996ec6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05fr-9000000000-571b504e001a1456ab10JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-9600000000-e4a123bb359dea0126e3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05g0-9000000000-30fdda4eee690af3ee50JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-285f7931bf8163b701daJSpectraViewer
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
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • 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
  • Cullin, C., Baudin-Baillieu, A., Guillemet, E., Ozier-Kalogeropoulos, O. (1996). "Functional analysis of YCL09C: evidence for a role as the regulatory subunit of acetolactate synthase." Yeast 12:1511-1518.8972574
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID15684
HMDB IDHMDB12141
Pubchem Compound ID440279
Kegg IDC04272
ChemSpider ID389255
FOODB IDFDB028799
Wikipedia IDNot Available
BioCyc IDDIOH-ISOVALERATE

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.