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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2008-08-13 15:46:23 UTC
Update Date2022-03-07 02:49:34 UTC
HMDB IDHMDB0006855
Secondary Accession Numbers
  • HMDB06855
Metabolite Identification
Common Name(S)-2-Acetolactate
Description(S)-2-Acetolactate, also known as b-dyn a, 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 (S)-2-Acetolactate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (S)-2-Acetolactate exists in all living species, ranging from bacteria to humans. Outside of the human body, (S)-2-Acetolactate has been detected, but not quantified in, several different foods, such as european chestnuts, rosemaries, half-highbush blueberries, pineapples, and chinese water chestnuts. This could make (S)-2-acetolactate a potential biomarker for the consumption of these foods.
Structure
Data?1600197959
Synonyms
ValueSource
(S)-2-Hydroxy-2-methyl-3-oxobutanoateChEBI
(2S)-2-Hydroxy-2-methyl-3-oxobutanoateKegg
(S)-2-Hydroxy-2-methyl-3-oxobutanoic acidGenerator
(2S)-2-Hydroxy-2-methyl-3-oxobutanoic acidGenerator
(S)-2-Acetolactic acidGenerator
13-Biotinyl-lys-dynorphin a amide (1-13)HMDB
b-DYN aHMDB
(S)-alpha-Acetolactic acidHMDB
(S)-α-Acetolactic acidHMDB
2-Acetolactic acidHMDB
2-Hydroxy-2-methyl-3-oxobutanoic acidHMDB
Acetolactic acidHMDB
Chemical FormulaC5H8O4
Average Molecular Weight132.1146
Monoisotopic Molecular Weight132.042258744
IUPAC Name(2S)-2-hydroxy-2-methyl-3-oxobutanoic acid
Traditional Nameacetolactic acid
CAS Registry Number71698-08-3
SMILES
CC(=O)[C@](C)(O)C(O)=O
InChI Identifier
InChI=1S/C5H8O4/c1-3(6)5(2,9)4(7)8/h9H,1-2H3,(H,7,8)/t5-/m0/s1
InChI KeyNMDWGEGFJUBKLB-YFKPBYRVSA-N
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
  • 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
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+129.78131661259
DarkChem[M-H]-123.7731661259
DeepCCS[M+H]+120.85830932474
DeepCCS[M-H]-116.99230932474
DeepCCS[M-2H]-154.40330932474
DeepCCS[M+Na]+129.69730932474
AllCCS[M+H]+130.732859911
AllCCS[M+H-H2O]+126.632859911
AllCCS[M+NH4]+134.532859911
AllCCS[M+Na]+135.732859911
AllCCS[M-H]-124.232859911
AllCCS[M+Na-2H]-126.932859911
AllCCS[M+HCOO]-130.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(S)-2-AcetolactateCC(=O)[C@](C)(O)C(O)=O2102.8Standard polar33892256
(S)-2-AcetolactateCC(=O)[C@](C)(O)C(O)=O992.8Standard non polar33892256
(S)-2-AcetolactateCC(=O)[C@](C)(O)C(O)=O1113.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(S)-2-Acetolactate,1TMS,isomer #1CC(=O)[C@](C)(O[Si](C)(C)C)C(=O)O1211.7Semi standard non polar33892256
(S)-2-Acetolactate,1TMS,isomer #2CC(=O)[C@](C)(O)C(=O)O[Si](C)(C)C1109.3Semi standard non polar33892256
(S)-2-Acetolactate,1TMS,isomer #3C=C(O[Si](C)(C)C)[C@](C)(O)C(=O)O1183.6Semi standard non polar33892256
(S)-2-Acetolactate,2TMS,isomer #1CC(=O)[C@](C)(O[Si](C)(C)C)C(=O)O[Si](C)(C)C1241.3Semi standard non polar33892256
(S)-2-Acetolactate,2TMS,isomer #2C=C(O[Si](C)(C)C)[C@](C)(O[Si](C)(C)C)C(=O)O1305.4Semi standard non polar33892256
(S)-2-Acetolactate,2TMS,isomer #3C=C(O[Si](C)(C)C)[C@](C)(O)C(=O)O[Si](C)(C)C1215.9Semi standard non polar33892256
(S)-2-Acetolactate,3TMS,isomer #1C=C(O[Si](C)(C)C)[C@](C)(O[Si](C)(C)C)C(=O)O[Si](C)(C)C1354.7Semi standard non polar33892256
(S)-2-Acetolactate,3TMS,isomer #1C=C(O[Si](C)(C)C)[C@](C)(O[Si](C)(C)C)C(=O)O[Si](C)(C)C1357.5Standard non polar33892256
(S)-2-Acetolactate,3TMS,isomer #1C=C(O[Si](C)(C)C)[C@](C)(O[Si](C)(C)C)C(=O)O[Si](C)(C)C1341.1Standard polar33892256
(S)-2-Acetolactate,1TBDMS,isomer #1CC(=O)[C@](C)(O[Si](C)(C)C(C)(C)C)C(=O)O1444.9Semi standard non polar33892256
(S)-2-Acetolactate,1TBDMS,isomer #2CC(=O)[C@](C)(O)C(=O)O[Si](C)(C)C(C)(C)C1354.7Semi standard non polar33892256
(S)-2-Acetolactate,1TBDMS,isomer #3C=C(O[Si](C)(C)C(C)(C)C)[C@](C)(O)C(=O)O1414.7Semi standard non polar33892256
(S)-2-Acetolactate,2TBDMS,isomer #1CC(=O)[C@](C)(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C1690.0Semi standard non polar33892256
(S)-2-Acetolactate,2TBDMS,isomer #2C=C(O[Si](C)(C)C(C)(C)C)[C@](C)(O[Si](C)(C)C(C)(C)C)C(=O)O1749.4Semi standard non polar33892256
(S)-2-Acetolactate,2TBDMS,isomer #3C=C(O[Si](C)(C)C(C)(C)C)[C@](C)(O)C(=O)O[Si](C)(C)C(C)(C)C1692.1Semi standard non polar33892256
(S)-2-Acetolactate,3TBDMS,isomer #1C=C(O[Si](C)(C)C(C)(C)C)[C@](C)(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2005.9Semi standard non polar33892256
(S)-2-Acetolactate,3TBDMS,isomer #1C=C(O[Si](C)(C)C(C)(C)C)[C@](C)(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C1994.3Standard non polar33892256
(S)-2-Acetolactate,3TBDMS,isomer #1C=C(O[Si](C)(C)C(C)(C)C)[C@](C)(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C1798.0Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (S)-2-Acetolactate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-0c1fe460a2ec8a1a255d2016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (S)-2-Acetolactate GC-MS (2 TMS) - 70eV, Positivesplash10-0303-9780000000-ed6c7b366835f2a4a9c02017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (S)-2-Acetolactate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-2-Acetolactate 10V, Positive-QTOFsplash10-001i-5900000000-a14af8bd96fdcce5e84f2015-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-2-Acetolactate 20V, Positive-QTOFsplash10-015l-9400000000-53c1f10a4a9b63a255742015-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-2-Acetolactate 40V, Positive-QTOFsplash10-01b9-9000000000-03c96ef4ce31ab174fdd2015-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-2-Acetolactate 10V, Negative-QTOFsplash10-0019-9700000000-641c507686f1b0493bde2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-2-Acetolactate 20V, Negative-QTOFsplash10-000i-9000000000-cd68c82882667330e3292015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-2-Acetolactate 40V, Negative-QTOFsplash10-0079-9000000000-f0530bd3c4f32baa697c2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-2-Acetolactate 10V, Negative-QTOFsplash10-000i-9300000000-0c998add67e750d36bc42021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-2-Acetolactate 20V, Negative-QTOFsplash10-000i-9200000000-3e8a380405cb5b02d1d72021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-2-Acetolactate 40V, Negative-QTOFsplash10-0006-9000000000-aeeb164d9240ff735bc52021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-2-Acetolactate 10V, Positive-QTOFsplash10-00ke-9200000000-c8b983df55a14da2898a2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-2-Acetolactate 20V, Positive-QTOFsplash10-0006-9000000000-79267be0bc618dc8018f2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-2-Acetolactate 40V, Positive-QTOFsplash10-0006-9000000000-cd1679ff8fbd31e9b90f2021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024120
KNApSAcK IDNot Available
Chemspider ID389710
KEGG Compound IDC06010
BioCyc ID2-ACETO-LACTATE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound440878
PDB IDNot Available
ChEBI ID18409
Food Biomarker OntologyNot Available
VMH IDALAC_S
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in magnesium ion binding
Specific function:
Not Available
Gene Name:
ILVBL
Uniprot ID:
A1L0T0
Molecular weight:
67867.2