Record Information
Version1.0
Creation date2011-09-21 00:21:20 UTC
Update date2015-07-21 06:57:25 UTC
Primary IDFDB022899
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name7a,12a-Dihydroxy-cholestene-3-one
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) [HMDB]
CAS NumberNot Available
Structure
Thumb
Synonyms
SynonymSource
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
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 FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC27H44O3
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
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 KeyInChIKey=VJGNBLOGSXHTLR-JFXJTJEYSA-N
Isomeric SMILES[H]O[C@]1([H])C([H])([H])C2([H])C([H])([H])C(=O)C([H])=C([H])[C@]2(C([H])([H])[H])[C@@]2([H])C([H])([H])[C@]([H])(O[H])[C@]3(C([H])([H])[H])[C@]([H])(C([H])([H])C([H])([H])[C@@]3([H])[C@]12[H])[C@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])[H]
Average Molecular Weight417
Monoisotopic Molecular Weight416
Classification
DescriptionThis compound belongs to the class of organic compounds known as cholesterols and derivatives. These 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
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-0957100000-f9ca360b20be30aee5cdView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0002-6421590000-060d19b9863c108036eaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kb-0009200000-ca011752a678df923d91View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-007k-2109000000-fe2eac67f433d8e5ffd6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0avi-7209000000-dd9edd2da2f8a7cfa3b7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0004900000-9a4838827d7cc0003b0cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-0009800000-d99dd5a2761313bbd19cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0012-1109000000-12f6e81d23b56a07105cView in MoNA
ChemSpider ID13628315
ChEMBL IDNot Available
KEGG Compound IDC05457
Pubchem Compound ID21252277
Pubchem Substance IDNot Available
ChEBI ID28477
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB02197
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
3-oxo-5-beta-steroid 4-dehydrogenaseAKR1D1P51857
3-oxo-5-alpha-steroid 4-dehydrogenase 2SRD5A2P31213
3-oxo-5-alpha-steroid 4-dehydrogenase 1SRD5A1P18405
Pathways
NameSMPDB LinkKEGG Link
Bile Acid BiosynthesisSMP00035 map00120
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference