EPICOPROSTEROL

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C27H48O
Molecular Weight	388.6694
Optical Activity	UNSPECIFIED
Defined Stereocenters	9 / 9
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=QYIXCDOBOSTCEI-KKFSNPNRSA-N

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

HIDE SMILES / InChI

Molecular Formula	C27H48O
Molecular Weight	388.6694
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	9 / 9
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17408835 | https://www.ncbi.nlm.nih.gov/pubmed/8866728

Epicoprostanol (3-alpha-hydroxy-5 beta-cholestanol or epicoprosterol) possesses the antioxidant properties; it also induced hypoglycemia and this achieved by a mechanism other than hyperinsulinemia. In addition, epicoprostanol was found in adipocere from human autopsies.

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596

PubMed

Title	Date	PubMed
Indole alkaloids and other constituents of Rauwolfia serpentina.	2005-06	15974606
Short-term LDL cholesterol-lowering efficacy of plant stanol esters.	2002-08-27	12197945
Tracing sewage in the marine environment: altered signatures in Concepción Bay, Chile.	2001-12	11791846
Antilithiasic and hypocholesterolemic effects of diets containing autoclaved amylomaize starch in hamster.	1995-12	8536509

Sample Use Guides

In Vivo Use Guide

diabetic rats: epicoprostanol significantly induced hypoglycemia and increased insulin levels in rat blood plasma by 88% and 66% compared to that of control after 2 h and 4 h of acute treatment at 100 mg/kg dose.

Route of Administration: Oral

In Vitro Use Guide

Ambrein and epicoprostanol were evaluated for their antioxidant potential in vitro by chemiluminescence (CL). Two low concentrations (5-20 microg/ml) of epicoprostanol inhibited CL significantly (P<0.001 and P<0.01, respectively) in comparison to DMSO control. The high concentration (40 microg/ml) of epicoprostanol behaved exceptionally and caused an increase in CL response that was more than control and significantly (P<0.001) higher than both the low concentrations.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 21:32:23 GMT 2025` Edited by `admin` on `Mon Mar 31 21:32:23 GMT 2025`
Record UNII	UFH3K1F9EG
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

EPICOPROSTEROL

Common Name

English

NSC-18182

Preferred Name

English

EPICOPROSTANOL

Common Name

English

CHOLESTAN-3-OL, (3.ALPHA.,5.BETA.)-

Systematic Name

English

5.BETA.-EPICHOLESTANOL

Common Name

English

EPICOPROSTANOL [USP-RS]

Common Name

English

.ALPHA.-COPROSTANOL

Common Name

English

Code System Code Type Description

FDA UNII

UFH3K1F9EG