COPROSTANONE

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 Search

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

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28879642 | https://www.ncbi.nlm.nih.gov/pubmed/19009227 | https://www.ncbi.nlm.nih.gov/pubmed/5569608

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

Targets

Primary Target	Pharmacology	Condition	Potency
Steroid 5-alpha-reductase 1 5 Target ID: CHEMBL1787 Sources: http://www.online-medical-dictionary.org/definitions-5/5-alpha-reductase-cholestenone.html \| https://www.ncbi.nlm.nih.gov/pubmed/9141518	Substrate 661

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

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	872053
Thin-layer and gas--liquid chromatographic identification of neutral steroids in human and rat feces.	1981 Mar	7240972
Metabolic variables of cholesterol during squalene feeding in humans: comparison with cholestyramine treatment.	1990 Sep	2246614
The oxidation of Delta2, Delta2,4 and Delta4,6 steroids with RuO4.	2004 Mar	15072919
Synthesis and antimicrobial evaluation of some novel cholestane heterocyclic derivatives.	2004 Mar	15038058
Synthesis of thiazolyl and thieno cholestane derivatives: a novel class of potent antiinflammatory steroids.	2005 May	15918579
The actinobacterial mce4 locus encodes a steroid transporter.	2008 Dec 19	18955493

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Fri Dec 15 19:49:55 GMT 2023` Edited by `admin` on `Fri Dec 15 19:49:55 GMT 2023`
Record UNII	H6B6EPA52O
Record Status	`Validated (UNII)`
Record Version

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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