ERGOSTEROL ENDOPEROXIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C28H44O3
Molecular Weight	428.6472
Optical Activity	UNSPECIFIED
Defined Stereocenters	10 / 10
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)[C@@H](C)\C=C\[C@@H](C)[C@H]1CC[C@@H]2[C@]1(C)CC[C@@H]3[C@@]4(C)CC[C@H](O)C[C@@]45OO[C@@]23C=C5

InChI

InChIKey=VXOZCESVZIRHCJ-KGHQQZOUSA-N

InChI=1S/C28H44O3/c1-18(2)19(3)7-8-20(4)22-9-10-23-25(22,5)13-12-24-26(6)14-11-21(29)17-27(26)15-16-28(23,24)31-30-27/h7-8,15-16,18-24,29H,9-14,17H2,1-6H3/b8-7+/t19-,20+,21-,22+,23+,24+,25+,26+,27+,28-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C28H44O3
Molecular Weight	428.6472
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	10 / 10
E/Z Centers	1
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22083593 | https://www.ncbi.nlm.nih.gov/pubmed/28436318 | https://www.ncbi.nlm.nih.gov/pubmed/10630115

Ergosterol endoperoxide is a derivative of ergosterol. It has been isolated from a variety of fungi, yeast, lichens and sponges. Ergosterol endoperoxide has been shown to inhibit the growth of some cancer cells and to induce apoptosis of HL60 human leukemia cells. Ergosterol endoperoxide also decreases lipid peroxidation of rat liver microsomes and suppresses the proliferation of mouse and human lymphocytes stimulated with mitogens. It has been reported as having immunosuppressive, antiplasmodial, antimycobacterial, antiviral, anti-inflammatory and antitumoural properties. The interaction of Trypanosoma cruzi with ergosterol peroxide in vitro resulted in a strong lytic activity possibly due to the disruption of the parasite membrane.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Beta-catenin pathway 1 Target ID: Beta-catenin pathway Sources: https://www.ncbi.nlm.nih.gov/pubmed/28761355 \| https://www.ncbi.nlm.nih.gov/pubmed/26210065	Inhibitor 8504
STAT3 signaling pathway 2 Target ID: STAT3 signaling pathway Sources: https://www.ncbi.nlm.nih.gov/pubmed/28761355	Inhibitor 8504
JAK2 signaling pathway 1 Target ID: JAK2 signaling pathway Sources: https://www.ncbi.nlm.nih.gov/pubmed/22260501	Inhibitor 8504

Conditions

Condition	Modality	Highest Phase	Product
Trypanosomiasis 9 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22083593	Curative	Basic research	Unknown Approved Use Unknown
Ovarian cancer 160 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28761355	Primary	Basic research	Unknown Approved Use Unknown
Multiple myeloma 159 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22260501	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Ergosterol peroxide inhibits ovarian cancer cell growth through multiple pathways.	2017	28761355
Ergosterol Peroxide: A Mushroom-Derived Compound with Promising Biological Activities-A Review.	2017	28436318
Ergosterol peroxide activates Foxo3-mediated cell death signaling by inhibiting AKT and c-Myc in human hepatocellular carcinoma cells.	2016-06-07	27058618
Ergosterol peroxide from Chaga mushroom (Inonotus obliquus) exhibits anti-cancer activity by down-regulation of the β-catenin pathway in colorectal cancer.	2015-09-15	26210065
Trypanocidal activity of ergosterol peroxide from Pleurotus ostreatus.	2012-06	22083593
Inhibition of STAT3 signaling and induction of SHP1 mediate antiangiogenic and antitumor activities of ergosterol peroxide in U266 multiple myeloma cells.	2012-01-20	22260501
Antitumor components from Naematoloma fasciculare.	2009-10	19884770
The antiplasmodial activity of isolates from Ajuga remota.	2002-05	12027771
Antimycobacterial ergosterol-5,8-endoperoxide from Ajuga remota.	1999-12	10630115
[The antiviral action of ergosterol peroxide].	1989-08	2594833
Ergosterol peroxide, an active compound from Inonotus radiatus.	1989-08	2813575
[Microbiological isomerization of ergosterol peroxide].	1969	5800491
ISOLATION OF ERGOSTEROL PEROXIDE FROM TRICHOPHYTON SCHOENLEINI.	1964-06-20	14217516

Patents

Sample Use Guides

In Vivo Use Guide

Mice: 100 mg/Kg

Route of Administration: Intraperitoneal

In Vitro Use Guide

Ergosterol endoperoxide from Ajuga remota showed a minimum inhibitory concentration (MIC) of 1 ug/ml against Mycobacterium tuberculosis.

Substance Class	Chemical Created by `admin` on `Wed Apr 02 18:42:44 GMT 2025` Edited by `admin` on `Wed Apr 02 18:42:44 GMT 2025`
Record UNII	UG9TN81TGH
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

ERGOSTEROL PEROXIDE

Preferred Name

English

ERGOSTEROL ENDOPEROXIDE

Official Name

English

(22E)-5.ALPHA.,8.ALPHA.-EPIDIOXYERGOSTA-6,22-DIEN-3.BETA.-OL

Common Name

English

3.BETA.-HYDROXY-5.ALPHA.,8.ALPHA.-EPIDIOXYERGOSTA-6,22-DIENE

Common Name

English

(24R)-ERGOST-5.ALPHA.,8.ALPHA.-EPIDIOXY-6,22-DIEN-3.BETA.-OL

Common Name

English

(22E,24R)-5.ALPHA.,8.ALPHA.-EPIDIOXYERGOSTA-6,22-DIEN-3.BETA.-OL

Common Name

English

ERGOSTEROL 5,8-PEROXIDE

Common Name

English

5.ALPHA.,8.ALPHA.-ERGOSTA-6,22-DIEN-3.BETA.-OL, 5,8-EPIDIOXY-

Common Name

English

5.ALPHA.,8.ALPHA.-EPIDIOXYERGOSTEROL

Common Name

English

NSC-31324

Code

English

5.ALPHA.,8.ALPHA.-EPIDOXY-(22E,24R)-ERGOSTA-6,22-DIEN-3.BETA.-OL

Common Name

English

PEROXYERGOSTEROL

Common Name

English

ERGOSTERYL PEROXIDE

Common Name

English

ERGOSTA-6,22-DIEN-3-OL, 5,8-EPIDIOXY-, (3.BETA.,5.ALPHA.,8.ALPHA.,22E)-

Common Name

English

Code System Code Type Description

NSC

31324