7a,12a-Dihydroxy-cholestene-3-one (CHEM035364)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:41:36 UTC
Update Date2016-11-09 01:21:18 UTC
Accession NumberCHEM035364
Identification
Common Name7a,12a-Dihydroxy-cholestene-3-one
ClassSmall Molecule
Description7a,12a-Dihydroxy-cholestene-3-one is an intermediate in bile acid synthesis; is considerably higher in patients with cerebrotendinous xanthomatosis (CTX) than in the normal liver. (PMID 7017048).
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
7-a,12-a-Dihydroxy-4-cholesten-3-oneHMDB
7-a,12-a-Dihydroxycholest-4-en-3-oneHMDB
7-a,12-alpha-Dihydroxy-4-cholesten-3-oneHMDB
7-a,12-alpha-Dihydroxycholest-4-en-3-oneHMDB
7-alpha,12-alpha-Dihydroxy-4-cholesten-3-oneHMDB
7-alpha,12-alpha-Dihydroxycholest-4-en-3-oneHMDB
7alpha,12alpha-Dihydroxy-cholestene-3-oneHMDB
Chemical FormulaC27H44O3
Average Molecular Mass416.637 g/mol
Monoisotopic Mass416.329 g/mol
CAS Registry NumberNot Available
IUPAC Name(1S,2R,9R,10R,11S,14R,15R,16S)-9,16-dihydroxy-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-3-en-5-one
Traditional Name(1S,2R,9R,10R,11S,14R,15R,16S)-9,16-dihydroxy-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-3-en-5-one
SMILES[H][C@@]12CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])[C@H](O)CC2CC(=O)C=C[C@]12C
InChI IdentifierInChI=1S/C27H44O3/c1-16(2)7-6-8-17(3)20-9-10-21-25-22(15-24(30)27(20,21)5)26(4)12-11-19(28)13-18(26)14-23(25)29/h11-12,16-18,20-25,29-30H,6-10,13-15H2,1-5H3/t17-,18?,20-,21+,22+,23-,24+,25+,26+,27-/m1/s1
InChI KeyVJGNBLOGSXHTLR-JFXJTJEYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassCholestane steroids
Direct ParentCholesterols and derivatives
Alternative Parents
Substituents
  • Cholesterol-skeleton
  • 3-oxo-delta-1-steroid
  • 3-oxosteroid
  • 7-hydroxysteroid
  • Oxosteroid
  • 12-hydroxysteroid
  • Hydroxysteroid
  • Delta-1-steroid
  • Cyclohexenone
  • Cyclic alcohol
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0029 g/LALOGPS
logP4.69ALOGPS
logP5.18ChemAxon
logS-5.2ALOGPS
pKa (Strongest Basic)-0.15ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity122.94 m³·mol⁻¹ChemAxon
Polarizability50.92 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-0957100000-f9ca360b20be30aee5cdSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0002-6421590000-060d19b9863c108036eaSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kb-0009200000-ca011752a678df923d91Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-007k-2109000000-fe2eac67f433d8e5ffd6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0avi-7209000000-dd9edd2da2f8a7cfa3b7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0004900000-9a4838827d7cc0003b0cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-0009800000-d99dd5a2761313bbd19cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0012-1109000000-12f6e81d23b56a07105cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0005900000-6e10002b2e4a4ff63704Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-6369100000-1f4ae070beee131b40ceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6u-9530000000-59dfe5c229199b50616dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000900000-67ea14fb7a26b9b2d929Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0001900000-949821f2e2f9dbbe8632Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udr-0079200000-cad453714d3d5275e24bSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0002197
FooDB IDFDB022899
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID6539
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID13628315
ChEBI ID28477
PubChem Compound ID21252277
Kegg Compound IDC05457
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Bjorkhem I, Oftebro H, Skrede S, Pedersen JI: Assay of intermediates in bile acid biosynthesis using isotope dilution--mass spectrometry: hepatic levels in the normal state and in cerebrotendinous xanthomatosis. J Lipid Res. 1981 Feb;22(2):191-200.