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Showing Compound 5beta-Coprostanol (FDB022125)

Record Information
Version1.0
Creation date2011-09-21 00:08:51 UTC
Update date2018-05-29 01:52:44 UTC
Primary IDFDB022125
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name5beta-Coprostanol
DescriptionCoprosterol or coprostanol is a cholesterol derivative found in human feces, gallstones, eggs, and other biological matter. Coprosterol is the odorous principle of feces. It is formed from the biohydrogenation of cholesterol (cholest-5en-3β-ol) in the gut of most higher animals and birds. This compound has frequently been used as a biomarker for the presence of human faecal matter in the environment. American physician Austin Flint named it stercorin . The transformation of cholesterol into coprosterol in its passage through the body involves a reduction of the C5:C6 double bond, and a transition from the allocholanic- to the cholanic-ring system. Although it is established that the bacterial flora of the intestine is concerned in the reduction process, the mechanism by which the stereochemical change is brought about is unknown. Current data suggests that cholestenone and coprostanone, and not cholesterol itself, are the immediate precursors of coprosterol which is formed from them in the intestine by bacterial reduction. [HMDB]
CAS Number360-68-9
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(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
(3b,5b)-cholestan-3-olhmdb
5beta-cholestan-3beta-olhmdb
5beta-Coprostanolhmdb
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
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC27H48O
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
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
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
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-MS5beta-Coprostanol, non-derivatized, GC-MS Spectrumsplash10-052u-9527000000-d23f4273340e8c85dc8aSpectrum
GC-MS5beta-Coprostanol, non-derivatized, GC-MS Spectrumsplash10-052u-9527000000-d23f4273340e8c85dc8aSpectrum
Predicted GC-MS5beta-Coprostanol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05i0-0109000000-761dcf3fe040f44fa80eSpectrum
Predicted GC-MS5beta-Coprostanol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0002-3104900000-654dcbe9dd07b5a589f2Spectrum
Predicted GC-MS5beta-Coprostanol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS5beta-Coprostanol, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-01-SG-2) , Positivesplash10-052u-9527000000-d23f4273340e8c85dc8a2012-08-31View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0079-0009000000-57023400d5e478a8c7462017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dr-3039000000-9ce6c0a362b9f376d3f02017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ab9-4159000000-32959ebb75235db63ac32017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-134a888410f8beddca3b2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0009000000-c42f43f5e21141f5a9092017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ab9-1009000000-8096d56c7bfdd221f9c22017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-34ef429285e58bb4b3142021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0009000000-780ac33d63315f6581592021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-0009000000-2b8e0e9916832dc478762021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0009000000-44afea742dee80d0734e2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9032000000-166905331dad000292e62021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4j-9820000000-f066461902c4fe39e2d42021-09-24View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Spectrum
ChemSpider ID191826
ChEMBL IDCHEMBL2048325
KEGG Compound IDNot Available
Pubchem Compound ID221122
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00577
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 IDCoprosterol
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