(R) 2,3-Dihydroxy-3-methylvalerate (ECMDB12140) (M2MDB000822)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (2)XML
Proteins (1010)
Record Information
Version2.0
Creation Date2012-05-31 14:20:42 -0600
Update Date2015-06-03 17:19:02 -0600
Secondary Accession Numbers
  • ECMDB12140
Identification
Name:(R) 2,3-Dihydroxy-3-methylvalerate
Description(R) 2,3-Dihydroxy-methylvalerate is an intermediate in valine, leucine and isoleucine biosynthesis. The pathway of valine biosynthesis is a four-step pathway that shares all of its steps with the parallel pathway of isoleucine biosynthesis. These entwined pathways are part of the superpathway of leucine, valine, and isoleucine biosynthesis, that generates not only isoleucine and valine, but also leucine. (R) 2,3-Dihydroxy-methylvalerate is generated from 3-Hydroxy-3-methyl-2-oxopentanoic acid via the enzyme ketol-acid reductoisomerase (EC 1.1.1.86) then it is converted to (S)-3-methyl-2-oxopentanoic via the dihydroxy-acid dehydratase (EC:4.2.1.9).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms:
  • (2R,3R)-2,3-dihydroxy-3-methylpentanoate
  • (2R,3R)-2,3-dihydroxy-3-methylpentanoic acid
  • (R) 2,3-Dihydroxy-3-methylvaleric acid
  • (R)-2,3-Dihydroxy-3-methylpentanoate
  • (R)-2,3-Dihydroxy-3-methylpentanoic acid
  • (R)-2,3-Dihydroxy-3-methylvalerate
  • (R)-2,3-Dihydroxy-3-methylvaleric acid
  • 1-Keto-2-methylvalerate
  • 1-Keto-2-methylvaleric acid
  • 2,3-Dihydroxy-3-Methyl-Valerate
  • 2,3-Dihydroxy-3-Methyl-Valeric acid
  • 2,3-Dihydroxy-3-methylpentanoate
  • 2,3-Dihydroxy-3-methylpentanoic acid
  • 2,3-Dihydroxy-Valerianate
  • 2,3-Dihydroxy-Valerianic Acid
  • 4,5-Dideoxy-3-C-methyl-pentonate
  • 4,5-Dideoxy-3-C-methyl-pentonic acid
  • a,b-Dihydroxy-b-methylvalerate
  • a,b-Dihydroxy-b-methylvaleric acid
  • Alpha,beta-Dihydroxy-beta-methylvalerate
  • Alpha,beta-Dihydroxy-beta-methylvaleric acid
  • CID8
  • DMV
  • α,β-Dihydroxy-β-methylvalerate
  • α,β-Dihydroxy-β-methylvaleric acid
Chemical Formula:C6H12O4
Weight:Average: 148.1571
Monoisotopic: 148.073558872
InChI Key:PDGXJDXVGMHUIR-UJURSFKZSA-N
InChI:InChI=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
CAS number:562-43-6
IUPAC Name:(2R,3R)-2,3-dihydroxy-3-methylpentanoic acid
Traditional IUPAC Name:(2R,3R)-2,3-dihydroxy-3-methylpentanoic acid
SMILES:CC[C@@](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 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:Cytoplasm
Reactions:
(R) 2,3-Dihydroxy-3-methylvalerate > 3-Methyl-2-oxovaleric acid + Water
2-Aceto-2-hydroxy-butyrate + Hydrogen ion + NADPH <> (R) 2,3-Dihydroxy-3-methylvalerate + NADP
(R) 2,3-Dihydroxy-3-methylvalerate + NADP <> (R)-3-Hydroxy-3-methyl-2-oxopentanoate + NADPH + Hydrogen ion
(R) 2,3-Dihydroxy-3-methylvalerate <> 3-Methyl-2-oxovaleric acid + Water
(R) 2,3-Dihydroxy-3-methylvalerate + NADP <> Hydrogen ion + 2-Aceto-2-hydroxy-butyrate + NADPH
(R) 2,3-Dihydroxy-3-methylvalerate + NADP > 2-Aceto-2-hydroxy-butyrate + NADPH
(R)-2,3-Dihydroxy-isovalerate + Hydrogen ion + NADPH + NADPH > NADP + (R) 2,3-Dihydroxy-3-methylvalerate
2-Aceto-2-hydroxy-butyrate + NADPH + Hydrogen ion + NADPH > NADP + (R) 2,3-Dihydroxy-3-methylvalerate
(R) 2,3-Dihydroxy-3-methylvalerate > Water + 3-Methyl-2-oxovaleric acid + 3-Methyl-2-oxovaleric acid
SMPDB Pathways:
Secondary Metabolites: Valine and I-leucine biosynthesis from pyruvatePW000978 ThumbThumb?image type=greyscaleThumb?image type=simple
Valine BiosynthesisPW000812 ThumbThumb?image type=greyscaleThumb?image type=simple
isoleucine biosynthesisPW000818 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
  • Valine, leucine and isoleucine biosynthesis ec00290
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-9000000000-d382043e81321879e92eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00tb-9464000000-0280de9eaa4c12333997View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05aj-7900000000-ed4255c918254a1dc462View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0kar-9600000000-420faa83ea76001db2e9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pb9-9000000000-393b15b5811231e32693View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udj-2900000000-d582074beb8b89338fa5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9400000000-5ee3e425ebda8358d337View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05g0-9000000000-db72ead6bd87a129b325View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0h32-2900000000-0dc4c2a3c02313bed77cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9000000000-431db2e8dea59bdd5c38View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-349f8877717c1418480eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-81689c0553421abfcd88View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9100000000-d9815468ea9acf930e9eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9100000000-f894bf4ab44aaac79501View 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
  • 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
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • 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 ID27512
HMDB IDHMDB12140
Pubchem Compound ID448154
Kegg IDC06007
ChemSpider ID395044
Wikipedia IDNot Available
BioCyc ID1-KETO-2-METHYLVALERATE
EcoCyc ID1-KETO-2-METHYLVALERATE
Ligand ExpoDMV

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.