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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:49:04 UTC
HMDB IDHMDB0000577
Secondary Accession Numbers
  • HMDB00577
Metabolite Identification
Common 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 (Wikipedia ). 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. Coprosterol is also a microbial metabolite, it can be produced by Lactobacillus (PMID: 20338415 ).
Structure
Data?1582752141
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 Weight388.6694
Monoisotopic Molecular Weight388.370516158
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
CAS Registry Number360-68-9
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-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
Ontology
Disposition

Biological location

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point102 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+197.64631661259
DarkChem[M-H]-195.5331661259
AllCCS[M+H]+204.93532859911
AllCCS[M-H]-201.75332859911
DeepCCS[M-2H]-238.36830932474
DeepCCS[M+Na]+212.34230932474
AllCCS[M+H]+204.932859911
AllCCS[M+H-H2O]+202.932859911
AllCCS[M+NH4]+206.832859911
AllCCS[M+Na]+207.332859911
AllCCS[M-H]-201.832859911
AllCCS[M+Na-2H]-203.732859911
AllCCS[M+HCOO]-205.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5beta-Coprostanol[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)C2298.6Standard polar33892256
5beta-Coprostanol[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)C3127.2Standard non polar33892256
5beta-Coprostanol[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)C3232.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5beta-Coprostanol,1TMS,isomer #1CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3096.0Semi standard non polar33892256
5beta-Coprostanol,1TBDMS,isomer #1CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3327.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 5beta-Coprostanol EI-B (Non-derivatized)splash10-052u-9527000000-d23f4273340e8c85dc8a2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 5beta-Coprostanol EI-B (Non-derivatized)splash10-052u-9527000000-d23f4273340e8c85dc8a2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5beta-Coprostanol GC-MS (Non-derivatized) - 70eV, Positivesplash10-05i0-0109000000-761dcf3fe040f44fa80e2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5beta-Coprostanol GC-MS (1 TMS) - 70eV, Positivesplash10-0002-3104900000-654dcbe9dd07b5a589f22017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5beta-Coprostanol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5beta-Coprostanol GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 5beta-Coprostanol EI-B (JEOL JMS-01-SG-2) , Positive-QTOFsplash10-052u-9527000000-d23f4273340e8c85dc8a2012-08-31HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5beta-Coprostanol 10V, Positive-QTOFsplash10-0079-0009000000-57023400d5e478a8c7462017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5beta-Coprostanol 20V, Positive-QTOFsplash10-00dr-3039000000-9ce6c0a362b9f376d3f02017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5beta-Coprostanol 40V, Positive-QTOFsplash10-0ab9-4159000000-32959ebb75235db63ac32017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5beta-Coprostanol 10V, Negative-QTOFsplash10-000i-0009000000-134a888410f8beddca3b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5beta-Coprostanol 20V, Negative-QTOFsplash10-000i-0009000000-c42f43f5e21141f5a9092017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5beta-Coprostanol 40V, Negative-QTOFsplash10-0ab9-1009000000-8096d56c7bfdd221f9c22017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5beta-Coprostanol 10V, Negative-QTOFsplash10-000i-0009000000-34ef429285e58bb4b3142021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5beta-Coprostanol 20V, Negative-QTOFsplash10-000i-0009000000-780ac33d63315f6581592021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5beta-Coprostanol 40V, Negative-QTOFsplash10-000i-0009000000-2b8e0e9916832dc478762021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5beta-Coprostanol 10V, Positive-QTOFsplash10-000i-0009000000-44afea742dee80d0734e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5beta-Coprostanol 20V, Positive-QTOFsplash10-0a4i-9032000000-166905331dad000292e62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5beta-Coprostanol 40V, Positive-QTOFsplash10-0a4j-9820000000-f066461902c4fe39e2d42021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Feces
Tissue Locations
  • Intestine
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
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothClostridium difficile infection details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Ulcerative colitis
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Crohn disease
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
Ulcerative colitis
  1. Azario I, Pievani A, Del Priore F, Antolini L, Santi L, Corsi A, Cardinale L, Sawamoto K, Kubaski F, Gentner B, Bernardo ME, Valsecchi MG, Riminucci M, Tomatsu S, Aiuti A, Biondi A, Serafini M: Neonatal umbilical cord blood transplantation halts skeletal disease progression in the murine model of MPS-I. Sci Rep. 2017 Aug 25;7(1):9473. doi: 10.1038/s41598-017-09958-9. [PubMed:28842642 ]
Crohn's disease
  1. Azario I, Pievani A, Del Priore F, Antolini L, Santi L, Corsi A, Cardinale L, Sawamoto K, Kubaski F, Gentner B, Bernardo ME, Valsecchi MG, Riminucci M, Tomatsu S, Aiuti A, Biondi A, Serafini M: Neonatal umbilical cord blood transplantation halts skeletal disease progression in the murine model of MPS-I. Sci Rep. 2017 Aug 25;7(1):9473. doi: 10.1038/s41598-017-09958-9. [PubMed:28842642 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022125
KNApSAcK IDNot Available
Chemspider ID191826
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCoprosterol
METLIN ID5559
PubChem Compound221122
PDB IDNot Available
ChEBI ID89519
Food Biomarker OntologyNot Available
VMH IDCOPROST
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceLieber, Iris Ilona. Metabolism of cholesterol. New theory of the formation of coprosterol. Prensa Medica Argentina (1960), 47 3097-3100.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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. [PubMed:9746261 ]
  2. 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. [PubMed:7380334 ]
  3. 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. [PubMed:6847274 ]
  4. 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. [PubMed:12092571 ]
  5. 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. [PubMed:7240972 ]
  6. 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. [PubMed:437403 ]
  7. 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. [PubMed:15621423 ]
  8. 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. [PubMed:20338415 ]