Canmetcon
Record Information
Version2.0
Creation Date2012-05-31 14:09:46 -0600
Update Date2015-06-03 15:54:55 -0600
Secondary Accession Numbers
  • ECMDB06855
Identification
Name:(S)-2-Acetolactate
Description:(S)-2-Acetolactate is an intermediate in the biosynthesis of valine, leucine and isoleucine (KEGG ID C06010 ). It is the sixth to last step in the synthesis of protein and is converted from 2-hydroxy-3-methyl-2-oxobutanoate via the enzyme acetolactate synthase [EC:2.2.1.6]. It is then converted to 3-hydroxy-3-methyl-2-oxobutanoate via the enzyme ketol-acid reductoisomerase [EC:1.1.1.86].
Structure
Thumb
Synonyms:
  • (S)-2-Acetolactic acid
  • (S)-2-Hydroxy-2-methyl-3-oxobutanoate
  • (S)-2-Hydroxy-2-methyl-3-oxobutanoic acid
  • 2-Ac
Chemical Formula:C5H8O4
Weight:Average: 132.1146
Monoisotopic: 132.042258744
InChI Key:NMDWGEGFJUBKLB-YFKPBYRVSA-N
InChI:InChI=1S/C5H8O4/c1-3(6)5(2,9)4(7)8/h9H,1-2H3,(H,7,8)/t5-/m0/s1
CAS number:Not Available
IUPAC Name:(2S)-2-hydroxy-2-methyl-3-oxobutanoic acid
Traditional IUPAC Name:acetolactic acid
SMILES:CC(=O)[C@](C)(O)C(O)=O
Chemical Taxonomy
DescriptionThis compound 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
  • Beta-keto acid
  • Branched fatty acid
  • Hydroxy fatty acid
  • Short-chain keto acid
  • Methyl-branched fatty acid
  • Alpha-hydroxy acid
  • Fatty acyl
  • Acyloin
  • Beta-hydroxy ketone
  • Hydroxy acid
  • Tertiary alcohol
  • Alpha-hydroxy ketone
  • Ketone
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carbonyl group
  • Alcohol
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • 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 Solubility286 g/LALOGPS
logP-0.65ALOGPS
logP-0.28ChemAxon
logS0.33ALOGPS
pKa (Strongest Acidic)3.45ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity28.59 m³·mol⁻¹ChemAxon
Polarizability11.81 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Pantothenate and CoA biosynthesisPW000828 ThumbThumb?image type=greyscaleThumb?image type=simple
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
KEGG Pathways:
  • C5-Branched dibasic acid metabolism ec00660
  • Metabolic pathways eco01100
  • Pantothenate and CoA biosynthesis ec00770
  • 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 (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-0c1fe460a2ec8a1a255dView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0303-9780000000-ed6c7b366835f2a4a9c0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-5900000000-a14af8bd96fdcce5e84fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-015l-9400000000-53c1f10a4a9b63a25574View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01b9-9000000000-03c96ef4ce31ab174fddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0019-9700000000-641c507686f1b0493bdeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9000000000-cd68c82882667330e329View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0079-9000000000-f0530bd3c4f32baa697cView in MoNA
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 ID18409
HMDB IDHMDB06855
Pubchem Compound ID440878
Kegg IDC06010
ChemSpider ID389710
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

General function:
Involved in magnesium ion binding
Specific function:
2 pyruvate = 2-acetolactate + CO(2)
Gene Name:
ilvI
Uniprot ID:
P00893
Molecular weight:
62984
Reactions
2 pyruvate = 2-acetolactate + CO(2).
General function:
Involved in acetolactate synthase activity
Specific function:
2 pyruvate = 2-acetolactate + CO(2)
Gene Name:
ilvH
Uniprot ID:
P00894
Molecular weight:
17977
Reactions
2 pyruvate = 2-acetolactate + CO(2).
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.
General function:
Involved in magnesium ion binding
Specific function:
2 pyruvate = 2-acetolactate + CO(2)
Gene Name:
ilvB
Uniprot ID:
P08142
Molecular weight:
60440
Reactions
2 pyruvate = 2-acetolactate + CO(2).
General function:
Involved in amino acid binding
Specific function:
2 pyruvate = 2-acetolactate + CO(2)
Gene Name:
ilvN
Uniprot ID:
P0ADF8
Molecular weight:
11106
Reactions
2 pyruvate = 2-acetolactate + CO(2).
General function:
Involved in acetolactate synthase activity
Specific function:
2 pyruvate = 2-acetolactate + CO(2)
Gene Name:
ilvM
Uniprot ID:
P0ADG1
Molecular weight:
9703
Reactions
2 pyruvate = 2-acetolactate + CO(2).