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(R)-2,3-Dihydroxy-isovalerate (M2MDB000589)

Record Information
Version2.0
Creation Date2012-05-31 14:03:51 -0600
Update Date2015-06-03 15:54:41 -0600
Secondary Accession Numbers
  • ECMDB04059
Identification
Name:(R)-2,3-Dihydroxy-isovalerate
Description(r)-2,3-dihydroxy-isovalerate belongs to the class of Branched Fatty Acids. These are fatty acids containing a branched chain. (inferred from compound structure)
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms:
  • α,β-dihydroxy-isovalerate
  • α,β-dihydroxy-isovaleric acid
  • (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-isovaleric acid
  • 2,3-dihydroxy-isovalerate
  • 2,3-Dihydroxy-isovaleric acid
Chemical Formula:C5H10O4
Weight:Average: 134.1305
Monoisotopic: 134.057908808
InChI Key:JTEYKUFKXGDTEU-VKHMYHEASA-N
InChI:InChI=1S/C5H10O4/c1-5(2,9)3(6)4(7)8/h3,6,9H,1-2H3,(H,7,8)/t3-/m0/s1
CAS number:Not Available
IUPAC Name:(2R)-2,3-dihydroxy-3-methylbutanoic acid
Traditional IUPAC Name:(R)-2,3-dihydroxy-isovalerate
SMILES:CC(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
State:Solid
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
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:Cytoplasm
Reactions:
(R)-2,3-Dihydroxy-isovalerate > alpha-Ketoisovaleric acid + Water
(R)-2,3-Dihydroxy-isovalerate + NADP <> (S)-2-Acetolactate + Hydrogen ion + NADPH
(R)-2,3-Dihydroxy-isovalerate + NADP <> 3-Hydroxy-3-methyl-2-oxobutanoic acid + NADPH + Hydrogen ion
(R)-2,3-Dihydroxy-isovalerate <> alpha-Ketoisovaleric acid + Water
(R)-2,3-Dihydroxy-isovalerate + NADP <> (<i>S</i>)-2-acetolactate + NADPH + Hydrogen ion
(R)-2,3-Dihydroxy-isovalerate + NADP > (S)-2-Acetolactate + NADPH
(R)-2,3-Dihydroxy-isovalerate + Hydrogen ion + NADPH + NADPH > NADP + (R) 2,3-Dihydroxy-3-methylvalerate
(S)-2-Acetolactate + Hydrogen ion + NADPH + NADPH > NADP + (R)-2,3-Dihydroxy-isovalerate
(R)-2,3-Dihydroxy-isovalerate > Water + Isovaleric acid
(R)-2,3-Dihydroxy-isovalerate > alpha-Ketoisovaleric acid + Water
SMPDB Pathways:
Pantothenate and CoA biosynthesisPW000828 ThumbThumb?image type=greyscaleThumb?image type=simple
Valine BiosynthesisPW000812 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9000000000-59e6990530d950227520View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00s9-9473000000-9708bfc20ee5ae043678View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-4900000000-196ffbbf313a33f24f27View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00ri-9300000000-aebebbbe2c7c11465a67View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-92af6a04d8cb7601ab35View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0019-9500000000-2837622949a6bd688094View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00s9-9400000000-0fc7aa81197fc5feb444View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dr-9000000000-45f3b95b2f30ea8445c1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-2900000000-fab4ee9aeca7067a9207View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-9100000000-b3da44872fd12f996ec6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05fr-9000000000-571b504e001a1456ab10View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-9600000000-e4a123bb359dea0126e3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05g0-9000000000-30fdda4eee690af3ee50View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-285f7931bf8163b701daView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID15684
HMDB IDHMDB12141
Pubchem Compound ID440279
Kegg IDC04272
ChemSpider ID389255
Wikipedia IDNot Available
BioCyc IDDIOH-ISOVALERATE
EcoCyc IDDIOH-ISOVALERATE

Enzymes

Protein Details
1. Dihydroxy-acid dehydratase
General function:
Involved in metabolic process
Specific function:
2,3-dihydroxy-3-methylbutanoate = 3-methyl-2- oxobutanoate + H(2)O
Gene Name:
ilvD
Uniprot ID:
P05791
Molecular weight:
65531
Reactions
2,3-dihydroxy-3-methylbutanoate = 3-methyl-2-oxobutanoate + H(2)O.
Protein Details
2. Ketol-acid reductoisomerase
General function:
Involved in oxidation-reduction process
Specific function:
(R)-2,3-dihydroxy-3-methylbutanoate + NADP(+) = (S)-2-hydroxy-2-methyl-3-oxobutanoate + NADPH
Gene Name:
ilvC
Uniprot ID:
P05793
Molecular weight:
54069
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.