5alpha-Cholestanone (CHEM034984)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:23:42 UTC
Update Date2016-11-09 01:21:13 UTC
Accession NumberCHEM034984
Identification
Common Name5alpha-Cholestanone
ClassSmall Molecule
DescriptionA 3-oxo-5alpha- steroid that is 5alpha-cholestane substituted by an oxo group at position 3.
Contaminant Sources
  • FooDB Chemicals
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
5a-CholestanoneGenerator
5Α-cholestanoneGenerator
(5a,17b)-17-Octylandrostan-3-oneHMDB
(5alpha)-Cholestan-3-oneHMDB
(5alpha)-CholestanoneHMDB
5a(H)-Cholestan-3-oneHMDB
5a-Cholestan-3-oneHMDB
5alpha-Cholestane-3-oneHMDB
5alpha-CoprostanoneHMDB
Coprostanone, (5alpha)-isomerHMDB
Coprostanone, (5beta)-isomerHMDB
CoprostanoneHMDB
5-alpha-Cholestan-3-oneHMDB
Chemical FormulaC27H46O
Average Molecular Mass386.654 g/mol
Monoisotopic Mass386.355 g/mol
CAS Registry Number566-88-1
IUPAC Name(1S,2S,7S,10R,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-one
Traditional Name(1S,2S,7S,10R,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-one
SMILES[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@@]4([H])CC(=O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C
InChI IdentifierInChI=1S/C27H46O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h18-20,22-25H,6-17H2,1-5H3/t19-,20+,22+,23-,24+,25+,26+,27-/m1/s1
InChI KeyPESKGJQREUXSRR-UXIWKSIVSA-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-5-alpha-steroid
  • Oxosteroid
  • 3-oxosteroid
  • Cyclic ketone
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
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 Solubility1.4e-05 g/LALOGPS
logP6.65ALOGPS
logP7.73ChemAxon
logS-7.4ALOGPS
pKa (Strongest Basic)-7.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity118.74 m³·mol⁻¹ChemAxon
Polarizability50.39 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-054o-3920000000-1e285528ee9f0b57935dSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-054o-3920000000-6bb813789665ec6a1628Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-054o-3920000000-1e285528ee9f0b57935dSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-054o-3920000000-6bb813789665ec6a1628Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05fr-1119000000-9809fd6827c971c15cbdSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-0009000000-4d86603e7a3a04181d6bSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-001i-9700000000-ab5536500bf3ce457af0Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-05nf-9400000000-df0bf747717b6f902997Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0009000000-d67fc5e4a90e5d444b4cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0avr-3109000000-6cb93905134a4bd15b66Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0abc-4129000000-9147166fdcb0a41b5fb9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-dc54e67e8b668159df03Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0009000000-e72d372e493f1796a572Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-066u-2019000000-49f63f8ed5d9e7e3d673Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-c037f2d2f217e99b79acSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0009000000-c037f2d2f217e99b79acSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-0009000000-0799374e96775b3163dbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0009000000-85d8a5bf63fedb0c361cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06dj-9164000000-a2efdb351bfe2dea81fdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9710000000-de7ec5cb56f34f7b69c5Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
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 IDHMDB0000871
FooDB IDFDB022292
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID5832
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID83174
ChEBI ID17762
PubChem Compound ID92128
Kegg Compound IDC03238
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10417325
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=15038058
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=15918579
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=17018531
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=4381999
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=494355
7. Cargill, D. I. The separation of cholesterol from related stanols and stanones by thin-layer chromatography. Analyst (1962), 87 865-9.
8. Strandberg TE, Tilvis RS, Miettinen TA: Metabolic variables of cholesterol during squalene feeding in humans: comparison with cholestyramine treatment. J Lipid Res. 1990 Sep;31(9):1637-43.
9. McNamara DJ, Proia A, Miettinen TA: Thin-layer and gas--liquid chromatographic identification of neutral steroids in human and rat feces. J Lipid Res. 1981 Mar;22(3):474-84.
10. Reddy BS, Wynder EL: Metabolic epidemiology of colon cancer. Fecal bile acids and neutral sterols in colon cancer patients and patients with adenomatous polyps. Cancer. 1977 Jun;39(6):2533-9.