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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2005-12-15 14:12:02 UTC
Update Date2022-03-07 02:49:10 UTC
HMDB IDHMDB0001569
Secondary Accession Numbers
  • HMDB01569
Metabolite Identification
Common NameEpi-coprostanol
DescriptionEpi-coprostanol, also known as epicholestanol or presteron, belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Thus, epi-coprostanol is considered to be a sterol lipid molecule. Epi-coprostanol is a very hydrophobic molecule, practically insoluble in water, and relatively neutral.
Structure
Thumb
Synonyms
Chemical FormulaC27H48O
Average Molecular Weight388.6694
Monoisotopic Molecular Weight388.370516158
IUPAC Name(1S,2S,5R,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
Traditional Name(1S,2S,5R,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
CAS Registry Number516-95-0
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
InChI Identifier
InChI=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-FBVYSKEZSA-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
  • Cholesterol
  • 3-alpha-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
Disposition
Biological locationRoute of exposureSource
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point113 - 114 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.00034 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022694
KNApSAcK IDNot Available
Chemspider ID59456
KEGG Compound IDC12978
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6329
PubChem Compound66066
PDB IDNot Available
ChEBI ID31542
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1900681
References
Synthesis ReferenceRuzicka, L.; Brungger, H.; Eichenberger, E.; Meyer, Jules. Polyterpenes and polyterpenoids. XCI. Preparation of coprosterol, epicoprosterol and epihydrocholesterol. Spatial position of the hydroxyl group in the sterols. Helvetica Chimica Acta (1934), 17 1407-16.
Material Safety Data Sheet (MSDS)Not Available
General References