Showing metabocard for Cholesteryl acetate (BMDB0003822)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:06:10 UTC
Update Date2020-04-22 15:12:46 UTC
BMDB IDBMDB0003822
Secondary Accession Numbers
  • BMDB03822
Metabolite Identification
Common NameCholesteryl acetate
Description2-Methylacetoacetic acid, also known as 2-methyl-3-oxo-butyric acid or 2-acetylpropionic acid, 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. 2-Methylacetoacetic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). 2-Methylacetoacetic acid, with regard to humans, has been linked to the inborn metabolic disorder beta-ketothiolase deficiency.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-MethylacetoacetateGenerator
2-Methyl-3-oxo-butyric acidHMDB
2-Methyl-3-oxo-butyrateHMDB
2Methyl-3-ketovalerateHMDB
(+/-)-2-methyl-3-oxobutanoateHMDB
(+/-)-2-methyl-3-oxobutanoic acidHMDB
2-Acetylpropionic acidHMDB
2-Methyl-3-ketobutyric acidHMDB
2-Methyl-3-oxo-butanoateHMDB
2-Methyl-3-oxo-butanoic acidHMDB
2-Methyl-3-oxobutanoateHMDB
2-Methyl-3-oxobutanoic acidHMDB
2-Methyl-3-oxobutyric acidHMDB
2-Methyl-acetoacetic acidHMDB
3-oxo-2-Methylbutyric acidHMDB
a-Methylacetoacetic acidHMDB
alpha-MethylacetoacetateHMDB
alpha-Methylacetoacetic acidHMDB
(-)-2-Methyl-3-oxobutanoic acidHMDB
(2S)-2-Methyl-3-oxobutanoic acidHMDB
(S)-2-Acetylpropionic acidHMDB
(S)-2-Methyl-3-oxobutyric acidHMDB
(±)-2-methyl-3-oxobutanoic acidHMDB
3-Keto-2-methylbutyrateHMDB
3-Keto-2-methylbutyric acidHMDB
Α-methylacetoacetic acidHMDB
(-)-Cholesteryl acetateHMDB
(3b)-Cholest-5-en-3-ol acetateHMDB
3-Cholesteryl acetateHMDB
3b-Acetoxycholest-5-eneHMDB
Cholest-5-en-3b-ol acetateHMDB
Cholest-5-en-3b-yl acetateHMDB
Cholesterin acetateHMDB
Cholesterol 3-acetateHMDB
Cholesterol 3b-acetateHMDB
Cholesterol acetateHMDB
(2R,5S,15R)-2,15-Dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl acetic acidGenerator, HMDB
Cholesteryl acetateMeSH
Cholesteryl acetic acidGenerator
Chemical FormulaC29H48O2
Average Molecular Weight428.6902
Monoisotopic Molecular Weight428.36543078
IUPAC Name(2R,5S,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl acetate
Traditional Name(2R,5S,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl acetate
CAS Registry Number604-35-3
SMILES
CC(C)CCC[C@@H](C)C1CCC2C3CC=C4C[C@H](CC[C@]4(C)C3CC[C@]12C)OC(C)=O
InChI Identifier
InChI=1S/C29H48O2/c1-19(2)8-7-9-20(3)25-12-13-26-24-11-10-22-18-23(31-21(4)30)14-16-28(22,5)27(24)15-17-29(25,26)6/h10,19-20,23-27H,7-9,11-18H2,1-6H3/t20-,23+,24?,25?,26?,27?,28+,29-/m1/s1
InChI KeyXUGISPSHIFXEHZ-JUTJDYIZSA-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
  • Methyl-branched fatty acid
  • Short-chain keto acid
  • Beta-hydroxy ketone
  • Fatty acyl
  • 1,3-dicarbonyl compound
  • Ketone
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Organic oxide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP7.4ALOGPS
logP7.55ChemAxon
logS-7.5ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity129.77 m³·mol⁻¹ChemAxon
Polarizability54.7 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-02bf-2109300000-d3daeef50bbce5584939View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004r-1009700000-75bb09e926fdb5ac7c0aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05p9-3009100000-d5a2ee8dce72d331e392View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-3129100000-9dab52e2d47a8e71712eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004r-1005900000-4fa7cbcd3c7c1e4d6fe6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002r-3009400000-53d27c9208e07f1d2a86View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-066r-5009000000-d9a319830de6f045f243View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0003771
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023226
KNApSAcK IDNot Available
Chemspider ID24191898
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound150996
PDB IDNot Available
ChEBI ID37079
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available