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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
Structure of COPROSTANONE

SMILES

[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@]4([H])CC(=O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C

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

HIDE SMILES / InChI
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

Sources: DOI: 10.1002/cber.18960290193

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Metabolic epidemiology of colon cancer. Fecal bile acids and neutral sterols in colon cancer patients and patients with adenomatous polyps.
1977 Jun
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Unknown
Name Type Language
COPROSTANONE
Common Name English
(5.BETA.,17.BETA.)-17-OCTYLANDROSTAN-3-ONE
Systematic Name English
5.BETA.-CHOLESTANONE
Systematic Name English
5.BETA.-CHOLESTAN-3-ONE
Systematic Name English
.BETA.-CHOLESTANONE
Common Name English
5.BETA.-COPROSTAN-3-ONE
Common Name English
3-COPROSTANONE
Common Name English
CHOLESTAN-3-ONE, (5.BETA.)-
Systematic Name English
NSC-119031
Code English
Code System Code Type Description
CAS
601-53-6
Created by admin on Fri Dec 15 19:49:55 GMT 2023 , Edited by admin on Fri Dec 15 19:49:55 GMT 2023
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NSC
119031
Created by admin on Fri Dec 15 19:49:55 GMT 2023 , Edited by admin on Fri Dec 15 19:49:55 GMT 2023
PRIMARY
ECHA (EC/EINECS)
210-003-0
Created by admin on Fri Dec 15 19:49:55 GMT 2023 , Edited by admin on Fri Dec 15 19:49:55 GMT 2023
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FDA UNII
H6B6EPA52O
Created by admin on Fri Dec 15 19:49:55 GMT 2023 , Edited by admin on Fri Dec 15 19:49:55 GMT 2023
PRIMARY
PUBCHEM
92132
Created by admin on Fri Dec 15 19:49:55 GMT 2023 , Edited by admin on Fri Dec 15 19:49:55 GMT 2023
PRIMARY
EPA CompTox
DTXSID50862211
Created by admin on Fri Dec 15 19:49:55 GMT 2023 , Edited by admin on Fri Dec 15 19:49:55 GMT 2023
PRIMARY