Record Information
Version1.0
Creation date2010-04-08 22:10:00 UTC
Update date2019-11-26 03:06:14 UTC
Primary IDFDB012122
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCholestanol
Description5alpha-Cholestanol, also known as cholestanol or dihydrocholesterol, 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-cholestanol is considered to be a sterol lipid molecule. 5alpha-Cholestanol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 5alpha-Cholestanol is a potentially toxic compound.
CAS Number80-97-7
Structure
Thumb
Synonyms
SynonymSource
(3beta,5alpha)-Cholestan-3-olChEBI
CholestanolChEBI
DihydrocholesterolChEBI
ZymostanolChEBI
(3b,5a)-Cholestan-3-olGenerator
(3Β,5α)-cholestan-3-olGenerator
5a-CholestanolGenerator
5Α-cholestanolGenerator
5 alpha Cholestan 3 beta olHMDB
5 beta Cholestan 3 beta olHMDB
5 beta-Cholestan-3 beta-olHMDB
beta CholestanolHMDB
beta-Ol, 5 beta-cholestan-3HMDB
5 alpha Cholestan 3 alpha olHMDB
5 alpha-Cholestan-3 beta-olHMDB
Cholestan 3 olHMDB
Cholestanol, (3alpha, 5beta)-isomerHMDB
CoprosterolHMDB
beta-CholestanolHMDB
5 beta-Cholestan-3 alpha-olHMDB
CoprostanolHMDB
5 alpha-Cholestan-3 alpha-olHMDB
Cholestan-3-olHMDB
beta-Cholestan-3 beta-ol, 5HMDB
3b-Hydroxy-5a-cholestaneHMDB
3b-HydroxycholestaneHMDB
5a-Cholestan-3b-olHMDB
5a-DihydrocholesterolHMDB
Cholestan-3b-olHMDB
DihydrocholesterinHMDB
EpicholestanolHMDB
5alpha-CholestanolChEBI
β-Cholestanolbiospider
3-β-Cholestanolbiospider
3-beta-Cholestanolbiospider
3-beta-Hydroxycholestanebiospider
3β-Hydroxy-5α-cholestanebiospider
3β-Hydroxycholestanebiospider
3beta-Cholestanolbiospider
3beta-Hydroxy-5beta-cholestanolbiospider
5α-Cholestan-3β-olbiospider
5α-Cholestanolbiospider
Cholestan-3β-olbiospider
Dihydrolathosterolmanual
Lathostanolmanual
Predicted Properties
PropertyValueSource
Water Solubility1.5e-05 g/LALOGPS
logP7.02ALOGPS
logP7.52ChemAxon
logS-7.4ALOGPS
pKa (Strongest Acidic)18.3ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity119.77 m³·mol⁻¹ChemAxon
Polarizability51.27 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC27H48O
IUPAC name(1S,2S,5S,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-ol
InChI IdentifierInChI=1S/C27H48O/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/h18-25,28H,6-17H2,1-5H3/t19-,20+,21+,22+,23-,24+,25+,26+,27-/m1/s1
InChI KeyQYIXCDOBOSTCEI-QCYZZNICSA-N
Isomeric SMILES[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@@]4([H])C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C
Average Molecular Weight388.6694
Monoisotopic Molecular Weight388.370516158
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
  • Cholesterol
  • 3-beta-hydroxysteroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 83.44%; H 12.45%; O 4.12%DFC
Melting PointMp 142-143°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]22D +27.4 (CHCl3)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSCholestanol, 1 TMS, GC-MS Spectrumsplash10-0a7l-8910000000-cb54fe639b59ac574d48Spectrum
GC-MSCholestanol, non-derivatized, GC-MS Spectrumsplash10-0159-2971000000-c73c47a340a1d4a167e1Spectrum
GC-MSCholestanol, non-derivatized, GC-MS Spectrumsplash10-001c-9685000000-f1bd7d21900c66c26e86Spectrum
GC-MSCholestanol, non-derivatized, GC-MS Spectrumsplash10-0a7l-8910000000-cb54fe639b59ac574d48Spectrum
GC-MSCholestanol, non-derivatized, GC-MS Spectrumsplash10-0a4m-3920000000-deaba49a3e34c5a9a998Spectrum
Predicted GC-MSCholestanol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05i0-0109000000-761dcf3fe040f44fa80eSpectrum
Predicted GC-MSCholestanol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0002-3104900000-654dcbe9dd07b5a589f2Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-1019000000-713d1937c93d1a00cc54Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000j-9002000000-f96eb85165088475ddbcSpectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-05o1-9200000000-8819828d6963c4e8290dSpectrum
MS/MSLC-MS/MS Spectrum - EI-B (SHIMADZU LKB-9000B) , Positivesplash10-0159-2971000000-c73c47a340a1d4a167e1Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-01-SG-2) , Positivesplash10-001c-9685000000-f1bd7d21900c66c26e86Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0079-0009000000-57023400d5e478a8c746Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dr-3039000000-9ce6c0a362b9f376d3f0Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ab9-4159000000-32959ebb75235db63ac3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-134a888410f8beddca3bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0009000000-c42f43f5e21141f5a909Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ab9-1009000000-8096d56c7bfdd221f9c2Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
ChemSpider ID6413
ChEMBL IDCHEMBL1289436
KEGG Compound IDNot Available
Pubchem Compound ID6665
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00908
CRC / DFC (Dictionary of Food Compounds) IDBZT44-I:HDK21-W
EAFUS IDNot Available
Dr. Duke IDCHOLESTANOL
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 IDCholestanol
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— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).