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(R)-3-Hydroxy-3-methyl-2-oxopentanoate (M2MDB000863)

Record Information
Version2.0
Creation Date2012-05-31 14:22:54 -0600
Update Date2015-06-03 17:19:07 -0600
Secondary Accession Numbers
  • ECMDB20014
Identification
Name:(R)-3-Hydroxy-3-methyl-2-oxopentanoate
Description(r)-3-hydroxy-3-methyl-2-oxopentanoate belongs to the class of Branched Fatty Acids. These are fatty acids containing a branched chain. (inferred from compound structure)
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • (3R)-3-hydroxy-3-methyl-2-oxopentanoate
  • (3R)-3-hydroxy-3-methyl-2-oxopentanoic acid
  • (R)-3-hydroxy-3-methyl-2-oxopentanoate
  • (R)-3-hydroxy-3-methyl-2-oxopentanoic acid
  • (R)-3-hydroxy-3-methyl-2-oxovalerate
  • (R)-3-hydroxy-3-methyl-2-oxovaleric acid
Chemical Formula:C6H10O4
Weight:Average: 146.1412
Monoisotopic: 146.057908808
InChI Key:YJVOWRAWFXRESP-ZCFIWIBFSA-N
InChI:InChI=1S/C6H10O4/c1-3-6(2,10)4(7)5(8)9/h10H,3H2,1-2H3,(H,8,9)/t6-/m1/s1
CAS number:Not Available
IUPAC Name:(3R)-3-hydroxy-3-methyl-2-oxopentanoic acid
Traditional IUPAC Name:(3R)-3-hydroxy-3-methyl-2-oxopentanoic acid
SMILES:CC[C@@](C)(O)C(=O)C(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassKeto acids and derivatives
Sub ClassShort-chain keto acids and derivatives
Direct ParentShort-chain keto acids and derivatives
Alternative Parents
Substituents
  • Branched fatty acid
  • Hydroxy fatty acid
  • Short-chain keto acid
  • Methyl-branched fatty acid
  • Alpha-keto acid
  • Acyloin
  • Fatty acyl
  • Tertiary alcohol
  • Alpha-hydroxy ketone
  • Ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organooxygen compound
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility99.8 g/LALOGPS
logP-0.03ALOGPS
logP0.77ChemAxon
logS-0.17ALOGPS
pKa (Strongest Acidic)3.16ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity33.42 m³·mol⁻¹ChemAxon
Polarizability13.7 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-3-methylvalerate + NADP <> (R)-3-Hydroxy-3-methyl-2-oxopentanoate + NADPH + Hydrogen ion
2-Aceto-2-hydroxy-butyrate <> (R)-3-Hydroxy-3-methyl-2-oxopentanoate
SMPDB Pathways:Not Available
KEGG Pathways:
  • Valine, leucine and isoleucine biosynthesis ec00290
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004j-3900000000-1c39941c4e6b3b9884dfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fmi-9600000000-94709bf8ae49b74e261aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zmi-9000000000-41b0b2ff7f0b177e07aaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f6t-3900000000-f53e055eb50930dbb30dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9400000000-690b9b7ffe779189afe6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9000000000-44075cd0923ea006902eView in MoNA
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
1D NMR1H 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
  • 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 ID49257
HMDB IDNot Available
Pubchem Compound ID11954026
Kegg IDC14463
ChemSpider ID10128321
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. 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.