Record Information
Version1.0
Creation date2011-09-21 00:11:38 UTC
Update date2015-10-09 22:29:21 UTC
Primary IDFDB022292
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name5alpha-Cholestanone
Description5alpha-Cholestanone, also known as 5α-cholestanone, belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Thus, 5alpha-cholestanone is considered to be a sterol lipid molecule. 5alpha-Cholestanone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
CAS Number566-88-1
Structure
Thumb
Synonyms
SynonymSource
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
5alpha-Cholestan-3-oneChEBI
5alpha-Cholestanonehmdb
5α-cholestan-3-oneGenerator
Predicted Properties
PropertyValueSource
Water Solubility1.5e-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
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC27H46O
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
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
Isomeric 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
Average Molecular Weight386.6535
Monoisotopic Molecular Weight386.354866094
Classification
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
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MS5alpha-Cholestanone, non-derivatized, GC-MS Spectrumsplash10-054o-3920000000-1e285528ee9f0b57935dSpectrum
GC-MS5alpha-Cholestanone, non-derivatized, GC-MS Spectrumsplash10-054o-3920000000-6bb813789665ec6a1628Spectrum
GC-MS5alpha-Cholestanone, non-derivatized, GC-MS Spectrumsplash10-054o-3920000000-1e285528ee9f0b57935dSpectrum
GC-MS5alpha-Cholestanone, non-derivatized, GC-MS Spectrumsplash10-054o-3920000000-6bb813789665ec6a1628Spectrum
Predicted GC-MS5alpha-Cholestanone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05fr-1119000000-9809fd6827c971c15cbdSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-0009000000-4d86603e7a3a04181d6bSpectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-001i-9700000000-ab5536500bf3ce457af0Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-05nf-9400000000-df0bf747717b6f902997Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0009000000-d67fc5e4a90e5d444b4cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0avr-3109000000-6cb93905134a4bd15b66Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0abc-4129000000-9147166fdcb0a41b5fb9Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-dc54e67e8b668159df03Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0009000000-e72d372e493f1796a572Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-066u-2019000000-49f63f8ed5d9e7e3d673Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
ChemSpider ID83174
ChEMBL IDCHEMBL69941
KEGG Compound IDC03238
Pubchem Compound ID92128
Pubchem Substance IDNot Available
ChEBI ID17762
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00871
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH 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
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference