Showing Compound Card for (S)-2-Aceto-2-hydroxybutanoic acid (CDB005122)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (1) Show 2 proteinsXML
Record Information
Version1.0
Created at2020-04-17 19:11:31 UTC
Updated at2020-12-07 19:11:37 UTC
CannabisDB IDCDB005122
Secondary Accession NumbersNot Available
Cannabis Compound 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. A 3-oxo monocarboxylic acid that is butanoic acid in which the hydrogens at position 2 are replaced by an acetyl and a hydroxy group (the S enantiomer) (S)-2-Aceto-2-hydroxybutanoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (S)-2-Aceto-2-hydroxybutanoic acid exists in all living species, ranging from bacteria to humans. (S)-2-Aceto-2-hydroxybutanoic acid is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
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 Weight146.14
Monoisotopic Molecular Weight146.0579
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

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS(S)-2-Aceto-2-hydroxybutanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9300000000-4a32387e4d1a3c2518e2Spectrum
Predicted GC-MS(S)-2-Aceto-2-hydroxybutanoic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-004i-9260000000-03d854f5c6e2c1cd66ccSpectrum
Predicted GC-MS(S)-2-Aceto-2-hydroxybutanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-1900000000-58139948a2d318b20cd32015-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-7900000000-5d95d041962e4d0c29c22015-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-9400000000-54a124cdee1ab9c9f3822015-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-3900000000-c26fd82bd80ef12ed78a2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pb9-9500000000-79a2c717c39914d907092015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ab9-9000000000-14cfb3f09136a8d1b1fd2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udj-0900000000-e31b2e7070d5d06bb4202021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0kam-9200000000-8e85855717b408d3368e2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-0a3fed2352239366e0952021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0kal-9600000000-fd5ff61bfd773a3d7ff12021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-775b97d756977d989ad02021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001r-9000000000-287791e86291cbac27492021-09-24View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Acetolactate synthase-like proteinILVBL19p13.1A1L0T0 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Acetolactate synthase-like proteinILVBL19p13.1A1L0T0 details
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0006900
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
References
General ReferencesNot Available

Enzymes

Enzyme Details
1. Acetolactate synthase-like protein
General function:
Involved in magnesium ion binding
Specific function:
Not Available
Gene Name:
ILVBL
Uniprot ID:
A1L0T0
Molecular weight:
67867.2