Canmetcon
Record Information
Version2.0
Creation Date2012-05-31 14:01:44 -0600
Update Date2015-06-03 15:54:36 -0600
Secondary Accession Numbers
  • ECMDB04002
Identification
Name:2-Acetolactate
Description:2-Acetolactate is involved in the butanoate metabolism and pantothenate and CoA biosynthesis pathways.
Structure
Thumb
Synonyms:
  • 2-Acetolactic acid
Chemical Formula:C5H8O4
Weight:Average: 132.1146
Monoisotopic: 132.042258744
InChI Key:NMDWGEGFJUBKLB-UHFFFAOYSA-N
InChI:InChI=1S/C5H8O4/c1-3(6)5(2,9)4(7)8/h9H,1-2H3,(H,7,8)
CAS number:Not Available
IUPAC Name:2-hydroxy-2-methyl-3-oxobutanoic acid
Traditional IUPAC Name:2-acetyllactic 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
Polarizability11.82 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
2-Oxopent-4-enoate metabolismPW001890 ThumbThumb?image type=greyscaleThumb?image type=simple
2-Oxopent-4-enoate metabolism 2PW002035 ThumbThumb?image type=greyscaleThumb?image type=simple
Pantothenate and CoA biosynthesisPW000828 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
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 ID16444
HMDB IDHMDB06833
Pubchem Compound ID22
Kegg IDC00900
ChemSpider ID21
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).