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coprostanol
Sign in to save5β-Coprostanol (5β-cholestan-3β-ol) is a 27-carbon stanol formed from the net reductive metabolism 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. 5β-coprostanol is thought to be exclusively bacterial in origin.
Chemical data
- Formula
- C27H48O
- Molecular weight
- 388.7 g/mol
- IUPAC name
- (3S,5R,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol
- SMILES
- C[C@H](CCCC(C)C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC[C@H]4[C@@]3(CC[C@@H](C4)O)C)C
- InChIKey
- QYIXCDOBOSTCEI-NWKZBHTNSA-N
- XLogP
- 9.4
- Polar surface area
- 20.2 Ų
- H-bond donors
- 1
- H-bond acceptors
- 1
- Formal charge
- 0
via PubChem
Wikidata facts
- Mass
- 388.370516156
Show 5 more facts
- found in taxon
- Homo sapiens
- chemical formula
- C₂₇H₄₈O
- isomeric SMILES
- O[C@H]4CC[C@]3([C@H](CC[C@H]2[C@@H]1CC[C@@H]([C@@]1(C)CC[C@@H]23)[C@H](C)CCCC(C)C)C4)C
- canonical SMILES
- OC1CCC2(C)C(CCC3C4CCC(C(C)CCCC(C)C)C4(C)CCC32)C1
- Commons category
- Coprostanol
via Wikidata · CC0
~9 min read
Encyclopedic overview
19 sectionsContents
- Chemical properties
- Solubility
- Degradation
- Chemical analysis
- Isomers
- Formation and occurrence
- Faecal sources
- Use as a tracer for sewage
- 5β-coprostanol / cholesterol ratio
- 5β-coprostanol / (5β-coprostanol + 5α-cholestanol) ratio
- 5β-coprostanol / total sterols ratio
- 5β-coprostanol / 24-ethyl coprostanol
- Epi-coprostanol / 5β-coprostanol
- Related markers
- 5α-cholestanol / cholesterol
- Use in archaeological studies
- See also
- References
- Further reading
5β-Coprostanol (5β-cholestan-3β-ol) is a 27-carbon stanol formed from the net reductive metabolism 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. 5β-coprostanol is thought to be exclusively bacterial in origin.
==Chemical properties==
Excerpted from Wikipedia’s “coprostanol” article, available under the CC BY-SA 4.0 licence.