Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C27H46O |
| Molecular Weight | 386.6535 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 8 / 8 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C
InChI
InChIKey=PESKGJQREUXSRR-JDIFZLMISA-N
InChI=1S/C27H46O/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/h18-20,22-25H,6-17H2,1-5H3/t19-,20-,22+,23-,24+,25+,26+,27-/m1/s1
| Molecular Formula | C27H46O |
| Molecular Weight | 386.6535 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 8 / 8 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Coprostanone is a metabolite of cholesterol. The conversion of cholesterol into coprostanol by intestinal microorganisms has been reported to occur by means of two different pathways. One pathway involves the intermediate formation of delta4-cholelestenone and coprostanone. In the other pathway, cholesterol is transformed into coprostanol by the direct reduction of the delta5 double bond. Coprostanone concentration is used as a fecal sterol biomarker in different investigations. For example, to determine of fecal sterols following a diet with and without plant sterols, to assess if faecal steroid excretion in humans is affected by calcium supplementation and other investigations.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Metabolic epidemiology of colon cancer. Fecal bile acids and neutral sterols in colon cancer patients and patients with adenomatous polyps. | 1977 Jun |
|
| Thin-layer and gas--liquid chromatographic identification of neutral steroids in human and rat feces. | 1981 Mar |
|
| Metabolic variables of cholesterol during squalene feeding in humans: comparison with cholestyramine treatment. | 1990 Sep |
|
| The oxidation of Delta2, Delta2,4 and Delta4,6 steroids with RuO4. | 2004 Mar |
|
| Synthesis and antimicrobial evaluation of some novel cholestane heterocyclic derivatives. | 2004 Mar |
|
| Synthesis of thiazolyl and thieno cholestane derivatives: a novel class of potent antiinflammatory steroids. | 2005 May |
|
| The actinobacterial mce4 locus encodes a steroid transporter. | 2008 Dec 19 |
Patents
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 19:58:07 GMT 2025
by
admin
on
Mon Mar 31 19:58:07 GMT 2025
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| Record UNII |
H6B6EPA52O
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| Record Status |
Validated (UNII)
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| Record Version |
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601-53-6
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119031
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210-003-0
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H6B6EPA52O
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92132
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DTXSID50862211
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| Related Record | Type | Details | ||
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PARENT -> METABOLITE |
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