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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2008-08-14 18:40:14 UTC
Update Date2022-03-07 02:49:34 UTC
HMDB IDHMDB0006900
Secondary Accession Numbers
  • HMDB0006854
  • HMDB06854
  • HMDB06900
Metabolite Identification
Common Name(S)-2-Aceto-2-hydroxybutanoic acid
Description(S)-2-Aceto-2-hydroxybutanoic acid, also known as (S)-2-hydroxy-2-ethyl-3-oxobutanoate or (S)-2-acetyl-2-hydroxybutyrate, 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-Aceto-2-hydroxybutanoic acid exists in all living species, ranging from bacteria to plants to humans (S)-2-Aceto-2-hydroxybutanoic acid has been detected, but not quantified in, several different foods, such as pitayas (Hylocereus undatus), lantern fruits (Physalis alkekengi), muscadine grapes (Vitis rotundifolia), american pokeweeds (Phytolacca americana), and okras (Abelmoschus esculentus). This could make (S)-2-aceto-2-hydroxybutanoic acid a potential biomarker for the consumption of these foods (S)-2-Aceto-2-hydroxybutanoic acid is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on (S)-2-Aceto-2-hydroxybutanoic acid.
Structure
Data?1592501086
Synonyms
ValueSource
(S)-2-Acetyl-2-hydroxybutyric acidChEBI
(S)-2-Hydroxy-2-ethyl-3-oxobutanoateKegg
(S)-2-Acetyl-2-hydroxybutyrateGenerator
(S)-2-Hydroxy-2-ethyl-3-oxobutanoic acidGenerator
(S)-2-Aceto-2-hydroxybutanoateGenerator
(2S)-2-Ethyl-2-hydroxy-3-oxobutanoateHMDB
(2S)-2-Ethyl-2-hydroxy-3-oxobutanoic acidHMDB
2S-Acetyl-2-hydroxy-butanoateGenerator, HMDB
(S)-2-Aceto-2-hydroxy-butyrateHMDB
2-Aceto-2-hydroxybutyric acidHMDB
2-Ethyl-2-hydroxy-3-oxobutanoic acidHMDB
Acetohydroxybutyric acidHMDB
alpha-Aceto-alpha-hydroxybutyric acidHMDB
alpha-Acetohydroxybutyric acidHMDB
α-Aceto-α-hydroxybutyric acidHMDB
α-Acetohydroxybutyric acidHMDB
Chemical FormulaC6H10O4
Average Molecular Weight146.1412
Monoisotopic Molecular Weight146.057908808
IUPAC Name(2S)-2-ethyl-2-hydroxy-3-oxobutanoic acid
Traditional Name(2S)-2-ethyl-2-hydroxy-3-oxobutanoic acid
CAS Registry Number113919-07-6
SMILES
CC[C@](O)(C(C)=O)C(O)=O
InChI Identifier
InChI=1S/C6H10O4/c1-3-6(10,4(2)7)5(8)9/h10H,3H2,1-2H3,(H,8,9)/t6-/m0/s1
InChI KeyVUQLHQFKACOHNZ-LURJTMIESA-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
  • 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
Disposition

Biological location

Source

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 Solubility259 g/LALOGPS
logP-0.58ALOGPS
logP0.24ChemAxon
logS0.25ALOGPS
pKa (Strongest Acidic)3.6ChemAxon
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity33.11 m³·mol⁻¹ChemAxon
Polarizability13.72 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]+133.24931661259
DarkChem[M-H]-127.59231661259
DeepCCS[M+H]+126.13830932474
DeepCCS[M-H]-122.30930932474
DeepCCS[M-2H]-159.48330932474
DeepCCS[M+Na]+134.98530932474
AllCCS[M+H]+133.532859911
AllCCS[M+H-H2O]+129.432859911
AllCCS[M+NH4]+137.332859911
AllCCS[M+Na]+138.432859911
AllCCS[M-H]-126.532859911
AllCCS[M+Na-2H]-128.832859911
AllCCS[M+HCOO]-131.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(S)-2-Aceto-2-hydroxybutanoic acidCC[C@](O)(C(C)=O)C(O)=O2148.0Standard polar33892256
(S)-2-Aceto-2-hydroxybutanoic acidCC[C@](O)(C(C)=O)C(O)=O1078.3Standard non polar33892256
(S)-2-Aceto-2-hydroxybutanoic acidCC[C@](O)(C(C)=O)C(O)=O1220.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(S)-2-Aceto-2-hydroxybutanoic acid,1TMS,isomer #1CC[C@](O[Si](C)(C)C)(C(C)=O)C(=O)O1258.0Semi standard non polar33892256
(S)-2-Aceto-2-hydroxybutanoic acid,1TMS,isomer #2CC[C@](O)(C(C)=O)C(=O)O[Si](C)(C)C1186.6Semi standard non polar33892256
(S)-2-Aceto-2-hydroxybutanoic acid,1TMS,isomer #3C=C(O[Si](C)(C)C)[C@@](O)(CC)C(=O)O1253.4Semi standard non polar33892256
(S)-2-Aceto-2-hydroxybutanoic acid,2TMS,isomer #1CC[C@](O[Si](C)(C)C)(C(C)=O)C(=O)O[Si](C)(C)C1307.6Semi standard non polar33892256
(S)-2-Aceto-2-hydroxybutanoic acid,2TMS,isomer #2C=C(O[Si](C)(C)C)[C@](CC)(O[Si](C)(C)C)C(=O)O1372.2Semi standard non polar33892256
(S)-2-Aceto-2-hydroxybutanoic acid,2TMS,isomer #3C=C(O[Si](C)(C)C)[C@@](O)(CC)C(=O)O[Si](C)(C)C1294.7Semi standard non polar33892256
(S)-2-Aceto-2-hydroxybutanoic acid,3TMS,isomer #1C=C(O[Si](C)(C)C)[C@](CC)(O[Si](C)(C)C)C(=O)O[Si](C)(C)C1439.0Semi standard non polar33892256
(S)-2-Aceto-2-hydroxybutanoic acid,3TMS,isomer #1C=C(O[Si](C)(C)C)[C@](CC)(O[Si](C)(C)C)C(=O)O[Si](C)(C)C1434.8Standard non polar33892256
(S)-2-Aceto-2-hydroxybutanoic acid,3TMS,isomer #1C=C(O[Si](C)(C)C)[C@](CC)(O[Si](C)(C)C)C(=O)O[Si](C)(C)C1393.3Standard polar33892256
(S)-2-Aceto-2-hydroxybutanoic acid,1TBDMS,isomer #1CC[C@](O[Si](C)(C)C(C)(C)C)(C(C)=O)C(=O)O1482.5Semi standard non polar33892256
(S)-2-Aceto-2-hydroxybutanoic acid,1TBDMS,isomer #2CC[C@](O)(C(C)=O)C(=O)O[Si](C)(C)C(C)(C)C1405.4Semi standard non polar33892256
(S)-2-Aceto-2-hydroxybutanoic acid,1TBDMS,isomer #3C=C(O[Si](C)(C)C(C)(C)C)[C@@](O)(CC)C(=O)O1473.9Semi standard non polar33892256
(S)-2-Aceto-2-hydroxybutanoic acid,2TBDMS,isomer #1CC[C@](O[Si](C)(C)C(C)(C)C)(C(C)=O)C(=O)O[Si](C)(C)C(C)(C)C1745.5Semi standard non polar33892256
(S)-2-Aceto-2-hydroxybutanoic acid,2TBDMS,isomer #2C=C(O[Si](C)(C)C(C)(C)C)[C@](CC)(O[Si](C)(C)C(C)(C)C)C(=O)O1809.0Semi standard non polar33892256
(S)-2-Aceto-2-hydroxybutanoic acid,2TBDMS,isomer #3C=C(O[Si](C)(C)C(C)(C)C)[C@@](O)(CC)C(=O)O[Si](C)(C)C(C)(C)C1758.3Semi standard non polar33892256
(S)-2-Aceto-2-hydroxybutanoic acid,3TBDMS,isomer #1C=C(O[Si](C)(C)C(C)(C)C)[C@](CC)(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2068.3Semi standard non polar33892256
(S)-2-Aceto-2-hydroxybutanoic acid,3TBDMS,isomer #1C=C(O[Si](C)(C)C(C)(C)C)[C@](CC)(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2046.2Standard non polar33892256
(S)-2-Aceto-2-hydroxybutanoic acid,3TBDMS,isomer #1C=C(O[Si](C)(C)C(C)(C)C)[C@](CC)(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C1854.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (S)-2-Aceto-2-hydroxybutanoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9300000000-4a32387e4d1a3c2518e22016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (S)-2-Aceto-2-hydroxybutanoic acid GC-MS (2 TMS) - 70eV, Positivesplash10-004i-9260000000-03d854f5c6e2c1cd66cc2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (S)-2-Aceto-2-hydroxybutanoic acid 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-Aceto-2-hydroxybutanoic acid 10V, Positive-QTOFsplash10-0002-1900000000-58139948a2d318b20cd32015-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-2-Aceto-2-hydroxybutanoic acid 20V, Positive-QTOFsplash10-004i-7900000000-5d95d041962e4d0c29c22015-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-2-Aceto-2-hydroxybutanoic acid 40V, Positive-QTOFsplash10-000i-9400000000-54a124cdee1ab9c9f3822015-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-2-Aceto-2-hydroxybutanoic acid 10V, Negative-QTOFsplash10-0udi-3900000000-c26fd82bd80ef12ed78a2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-2-Aceto-2-hydroxybutanoic acid 20V, Negative-QTOFsplash10-0pb9-9500000000-79a2c717c39914d907092015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-2-Aceto-2-hydroxybutanoic acid 40V, Negative-QTOFsplash10-0ab9-9000000000-14cfb3f09136a8d1b1fd2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-2-Aceto-2-hydroxybutanoic acid 10V, Negative-QTOFsplash10-0udj-0900000000-e31b2e7070d5d06bb4202021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-2-Aceto-2-hydroxybutanoic acid 20V, Negative-QTOFsplash10-0kam-9200000000-8e85855717b408d3368e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-2-Aceto-2-hydroxybutanoic acid 40V, Negative-QTOFsplash10-0006-9000000000-0a3fed2352239366e0952021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-2-Aceto-2-hydroxybutanoic acid 10V, Positive-QTOFsplash10-0kal-9600000000-fd5ff61bfd773a3d7ff12021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-2-Aceto-2-hydroxybutanoic acid 20V, Positive-QTOFsplash10-0006-9000000000-775b97d756977d989ad02021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-2-Aceto-2-hydroxybutanoic acid 40V, Positive-QTOFsplash10-001r-9000000000-287791e86291cbac27492021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart 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 IDFDB024147
KNApSAcK IDNot Available
Chemspider ID389708
KEGG Compound IDC06006
BioCyc ID2-ACETO-2-HYDROXY-BUTYRATE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound440875
PDB IDNot Available
ChEBI ID27681
Food Biomarker OntologyNot Available
VMH IDNot Available
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