?5-Avenosterol

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C29H48O
Molecular Weight	412.6908
Optical Activity	UNSPECIFIED
Defined Stereocenters	8 / 8
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC=C(CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)C(C)C

InChI

InChIKey=OSELKOCHBMDKEJ-WGMIZEQOSA-N

InChI=1S/C29H48O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h7,10,19-20,23-27,30H,8-9,11-18H2,1-6H3/b21-7-/t20-,23+,24+,25-,26+,27+,28+,29-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C29H48O
Molecular Weight	412.6908
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	8 / 8
E/Z Centers	1
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26455344 | https://www.ncbi.nlm.nih.gov/pubmed/28134973 | https://www.ncbi.nlm.nih.gov/pubmed/28637390 | https://www.ncbi.nlm.nih.gov/pubmed/23116181 | https://www.ncbi.nlm.nih.gov/pubmed/23994501https://www.ncbi.nlm.nih.gov/pubmed/2775538 | https://www.ncbi.nlm.nih.gov/pubmed/1186438 | https://www.ncbi.nlm.nih.gov/pubmed/5343809 | https://www.ncbi.nlm.nih.gov/pubmed/10576216 | https://www.ncbi.nlm.nih.gov/pubmed/24684169

The isomer of fucosterol, isofucosterol, has been identified as a minor constituent of marine sponge, Gynostemma pentafillum, oat seeds and a few other plants. Isofucosterol of marine sponge is believed to be the biosynthetic precursors of the antiviral orthoesterols and weinbersterols found in the same sponge. Isofucosterol exhibits lipase inhibitory effect, suggesting that it has potential as anti-obesity agent.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
LXR-alpha 10 Target ID: CHEMBL2808 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23116181	Agonist 2752	464.0 nM [EC50]
LXR-beta 6 Target ID: CHEMBL4093 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23116181	Agonist 2752	1391.0 nM [EC50]
lipid oxidation 20 Target ID: GO:0034440 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14560919	Inhibitor 8504
Aldose reductase 45 Target ID: CHEMBL1900 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23994501	Inhibitor 8504	143.0 µM [IC50]
Protein-tyrosine phosphatase 1B 34 Target ID: CHEMBL335 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23994501	Inhibitor 8504	77.13 µM [Ki]
FoxO signaling pathway 4 Target ID: map04068 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28134973	Modulator 846
Pancreatic triacylglycerol lipase 12 Target ID: CHEMBL1687677 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24684169	Inhibitor 8504

Conditions

Condition	Modality	Highest Phase	Product
Diabetes mellitus 93 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15595413	Primary	Preclinical	Unknown Approved Use Unknown
Plasmodium falciparum malaria 63 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28637390	Primary	Basic research	Unknown Approved Use Unknown
Obesity 206 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28134973	Primary	Basic research	Unknown Approved Use Unknown
Obesity 206 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24684169	Primary	Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Kinetics and molecular docking studies of an anti-diabetic complication inhibitor fucosterol from edible brown algae Eisenia bicyclis and Ecklonia stolonifera.	2013-10-25	23994501
Inhibitory activity on HIV-1 reverse transcriptase and integrase of a carmalol derivative from a brown Alga, Ishige okamurae.	2006-08	16775811
Inhibition of Mycobacterium tuberculosis growth by saringosterol from Lessonia nigrescens.	2001-11	11720535
28-Isofucosterol: major sterol of a marine sponge.	1975-07-01	1186438
Incorporation of (2-14C, (5r)-5-3H1) mevalonic acid into cholesterol by a rat liver homogenate and into beta-sitosterol and 28-isofucosterol by larix decidua leaves.	1969-10	5348842
Incorporation of [2-14C] mevalonic acid into 28-isofucosterol by leaves of Pisum sativum.	1969-10	5343809

Patents

Sample Use Guides

In Vivo Use Guide

Rat: 30 or 300 mg/kg

Route of Administration: Oral

In Vitro Use Guide

Fucosterol was found to be a mixed-type inhibitor of rat lens aldose reductase and human recombinant aldose reductase with Ki values of 7.03 μM and 99.50 μM, respectively.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 22:24:59 GMT 2025` Edited by `admin` on `Mon Mar 31 22:24:59 GMT 2025`
Record UNII	CS4PB4FQQ7
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

24-Ethylidenecholesterol

Preferred Name

English

?5-Avenosterol

Common Name

English

?5-Avenasterin

Common Name

English

Stigmasta-5,24(28)-dien-3-ol, (3?)-

Systematic Name

English

(3?)-Stigmasta-5,24(28)-dien-3-ol

Systematic Name

English

Code System Code Type Description

PUBCHEM

119074

Created by admin on Mon Mar 31 22:24:59 GMT 2025 , Edited by admin on Mon Mar 31 22:24:59 GMT 2025

PRIMARY

CAS

18472-36-1

Created by admin on Mon Mar 31 22:24:59 GMT 2025 , Edited by admin on Mon Mar 31 22:24:59 GMT 2025

PRIMARY

FDA UNII

CS4PB4FQQ7

Created by admin on Mon Mar 31 22:24:59 GMT 2025 , Edited by admin on Mon Mar 31 22:24:59 GMT 2025

PRIMARY

Details

SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Approved Use

Approved Use

Approved Use

Approved Use

PubMed

Patents

Sample Use Guides