5beta-Coprostanol (CHEM022839)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:56:11 UTC
Update Date2026-04-06 12:55:15 UTC
Accession NumberCHEM022839
Identification
Common Name5beta-Coprostanol
ClassSmall Molecule
DescriptionA member of the class of phytosterols that is 5beta-cholestane carrying a hydroxy substituent at the 3beta-position.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Feces
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(3beta,5beta)-Cholestan-3-olChEBI
5beta CoprostanolChEBI
5beta-Cholestan-3beta-olChEBI
CoprosterolChEBI
(3b,5b)-Cholestan-3-olGenerator
(3Β,5β)-cholestan-3-olGenerator
5b CoprostanolGenerator
5Β coprostanolGenerator
5b-Cholestan-3b-olGenerator
5Β-cholestan-3β-olGenerator
5b-CoprostanolGenerator
5Β-coprostanolGenerator
3b-Hydroxy-5b-cholestanolHMDB
StercorinHMDB
5 beta-Cholestan-3 beta-olHMDB
5 alpha Cholestan 3 alpha olHMDB
CoprostanolHMDB
5 beta-Cholestan-3 alpha-olHMDB
Cholestan 3 olHMDB
Cholestanol, (3alpha, 5beta)-isomerHMDB
beta-CholestanolHMDB
beta-Cholestan-3 beta-ol, 5HMDB
Cholestan-3-olHMDB
CholestanolHMDB
DihydrocholesterolHMDB
beta-Ol, 5 beta-cholestan-3HMDB
5 alpha Cholestan 3 beta olHMDB
beta CholestanolHMDB
5 alpha-Cholestan-3 alpha-olHMDB
5 alpha-Cholestan-3 beta-olHMDB
5 beta Cholestan 3 beta olHMDB
Chemical FormulaC27H48O
Average Molecular Mass388.669 g/mol
Monoisotopic Mass388.371 g/mol
CAS Registry Number360-68-9
IUPAC Name(1S,2S,5S,7R,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,5S,7R,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
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 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-NWKZBHTNSA-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-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
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 Solubility1.5e-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
Polarizability50.82 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 - EI-B (Non-derivatized)splash10-052u-9527000000-d23f4273340e8c85dc8aSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052u-9527000000-d23f4273340e8c85dc8aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05i0-0109000000-761dcf3fe040f44fa80eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0002-3104900000-654dcbe9dd07b5a589f2Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-01-SG-2) , Positivesplash10-052u-9527000000-d23f4273340e8c85dc8aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0079-0009000000-57023400d5e478a8c746Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dr-3039000000-9ce6c0a362b9f376d3f0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ab9-4159000000-32959ebb75235db63ac3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-134a888410f8beddca3bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0009000000-c42f43f5e21141f5a909Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ab9-1009000000-8096d56c7bfdd221f9c2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-34ef429285e58bb4b314Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0009000000-780ac33d63315f658159Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-0009000000-2b8e0e9916832dc47876Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0009000000-44afea742dee80d0734eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9032000000-166905331dad000292e6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4j-9820000000-f066461902c4fe39e2d4Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
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 IDHMDB0000577
FooDB IDFDB022125
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID5559
PDB IDNot Available
Wikipedia LinkCoprosterol
Chemspider ID191826
ChEBI ID89519
PubChem Compound ID221122
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=12092571
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=15621423
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=16115503
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=25455370
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=25467184
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=25770447
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=26132310
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=26228071
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=26310319
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=26657388
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=26871580
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=26874877
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=26910992
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=26994465
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=27087811
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=27139306
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=27167134
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=27207024
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=27630168
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=27696200
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=27839832
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=27995830
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=28060808
24. https://www.ncbi.nlm.nih.gov/pubmed/?term=28211537
25. Lieber, Iris Ilona. Metabolism of cholesterol. New theory of the formation of coprosterol. Prensa Medica Argentina (1960), 47 3097-3100.
26. Borjesson E, Sundin A, Leeming R, Torstensson L: New method for determination of fecal sterols in urine using non-chlorinated solvents. J Chromatogr B Biomed Sci Appl. 1998 Aug 25;713(2):438-42.
27. Kay RM, Cohen Z, Siu KP, Petrunka CN, Strasberg SM: Ileal excretion and bacterial modification of bile acids and cholesterol in patients with continent ileostomy. Gut. 1980 Feb;21(2):128-32.
28. Watne AL, Carrier JM, Durham JP, Hrabovsky EE, Chang W: The occurrence of carcinoma of the rectum following ileoproctostomy for familial polyposis. Ann Surg. 1983 May;197(5):550-4.
29. Schonning C, Leeming R, Stenstrom TA: Faecal contamination of source-separated human urine based on the content of faecal sterols. Water Res. 2002 Apr;36(8):1965-72.
30. 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.
31. Endo T, Uchida K, Amuro Y, Higashino K, Yamamura Y: Bile acid metabolism in benign recurrent intrahepatic cholestasis. Comparative studies on the icteric and anicteric phases of a single case. Gastroenterology. 1979 May;76(5 Pt 1):1002-6.
32. Veiga P, Juste C, Lepercq P, Saunier K, Beguet F, Gerard P: Correlation between faecal microbial community structure and cholesterol-to-coprostanol conversion in the human gut. FEMS Microbiol Lett. 2005 Jan 1;242(1):81-6.
33. Lye HS, Rusul G, Liong MT: Removal of cholesterol by lactobacilli via incorporation and conversion to coprostanol. J Dairy Sci. 2010 Apr;93(4):1383-92. doi: 10.3168/jds.2009-2574.