Showing metabocard for Epi-coprostanol (BMDB0001569)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:47:48 UTC
Update Date2020-04-22 15:08:44 UTC
BMDB IDBMDB0001569
Secondary Accession Numbers
  • BMDB01569
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. Based on a literature review a significant number of articles have been published on Epi-coprostanol.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(3-alpha,5-alpha)-Cholestan-3-olChEBI
3alpha-Hydroxy-5alpha-cholestaneChEBI
5alpha-Cholestan-3alpha-olChEBI
Epi-cholestanolChEBI
EpicholestanolChEBI
EpidehydrocholesterinChEBI
PresteronChEBI
DihydrinKegg
(3-a,5-a)-Cholestan-3-olGenerator
(3-Α,5-α)-cholestan-3-olGenerator
3a-Hydroxy-5a-cholestaneGenerator
3Α-hydroxy-5α-cholestaneGenerator
5a-Cholestan-3a-olGenerator
5Α-cholestan-3α-olGenerator
5b-Cholestan-3a-olHMDB
5b-Cholestane-3a-olHMDB
5b-CholestanolHMDB
5beta-Cholestan-3alpha-olHMDB
5beta-Cholestane-3alpha-olHMDB
5beta-CholestanolHMDB
a-CoprostanolHMDB
alpha-CoprostanolHMDB
Epi-coprosterolHMDB
EpicoprostanolHMDB
EpicoprosterolHMDB
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
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point113 - 114 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Polarizability51.12 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05i0-0109000000-761dcf3fe040f44fa80eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0002-3104900000-654dcbe9dd07b5a589f2View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-5db181960ec36b693dc5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0009000000-21dc22a0a9fa3809f268View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ab9-1009000000-c90e4e689bf7be60948cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-34ef429285e58bb4b314View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0009000000-780ac33d63315f658159View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-0009000000-2b8e0e9916832dc47876View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0079-0009000000-48703a10acd86b4a9369View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dr-3149000000-3dac80dba8a7c194a9a6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-4169000000-067270e2b2860f462b88View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0009000000-44afea742dee80d0734eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9032000000-166905331dad000292e6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4j-9820000000-f066461902c4fe39e2d4View in MoNA
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0001569
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
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 ReferencesNot Available