23-EPI-26-DEOXYACTEIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C37H56O10
Molecular Weight	660.8345
Optical Activity	UNSPECIFIED
Defined Stereocenters	18 / 18
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@]12C[C@@]3(C)[C@]4([H])CC[C@]5([H])[C@]6(C[C@@]46C[C@@H](OC(C)=O)[C@]3(C)[C@@]1([H])[C@H](C)C[C@@]7(OC[C@@]8(C)O[C@@H]78)O2)CC[C@H](O[C@]9([H])OC[C@@H](O)[C@H](O)[C@H]9O)C5(C)C

InChI

InChIKey=GCMGJWLOGKSUGX-WUHYQCRDSA-N

InChI=1S/C37H56O10/c1-18-12-37(30-33(6,47-30)17-43-37)46-21-13-32(5)23-9-8-22-31(3,4)24(45-29-28(41)27(40)20(39)15-42-29)10-11-35(22)16-36(23,35)14-25(44-19(2)38)34(32,7)26(18)21/h18,20-30,39-41H,8-17H2,1-7H3/t18-,20-,21+,22+,23+,24+,25-,26+,27+,28-,29+,30-,32+,33-,34-,35-,36+,37-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C37H56O10
Molecular Weight	660.8345
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	17 / 18
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21614156
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/14758092

23-epi-26-deoxyactein (formerly 27-deoxyactein), is the most abundant triterpene glycosides of black cohosh, inhibits growth of the MCF7 human breast cancer cells and induces cell cycle arrest at G1 and might eventually be useful in the prevention or treatment of breast cancer. Also was investigated the mechanism of action of 23-epi-26-deoxyactein, and was shown that 23-epi-26-deoxyactein decreased IFNγ-induced iNOS mRNA and NO production in brain microglial cells.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
nitric oxide production 1 Target ID: nitric oxide production Sources: https://www.ncbi.nlm.nih.gov/pubmed/21614156	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Breast cancer 434 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14758092	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Pharmacokinetics of 23-epi-26-deoxyactein in women after oral administration of a standardized extract of black cohosh.	2010 Feb	20032972

Patents

Sample Use Guides

In Vivo Use Guide

Single doses of black cohosh extract containing 1.4, 2.8, or 5.6 mg of 23-epi-26-deoxyactein were administered to 15 healthy, menopausal women

Route of Administration: Oral

In Vitro Use Guide

BV-2 murine microglia cells stimulated for 18 hours with LPS produced 29 ± 6 μM NO. 30 μg/ml 23-epi-26-deoxyactein had no effect on NO production, but inhibited IFNγ-induced NO production in a dose dependent fashion up to 14%, with a slight increase observed at the lower doses (0.3 μg/ml) of 23-epi-26 deoxyactein. 30 μg/ml 23-epi-26-deoxyactein slightly stimulated LPS-induced NO.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 08:33:16 GMT 2023` Edited by `admin` on `Sat Dec 16 08:33:16 GMT 2023`
Record UNII	2A97XP2V7I
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

23-EPI-26-DEOXYACTEIN

Common Name

English

23-EPI-26-DEOXYACTEIN (CONSTITUENT OF BLACK COHOSH) [DSC]

Common Name

English

23-EPI-26-DEOXYACTEIN [USP-RS]

Common Name

English

.BETA.-D-XYLOPYRANOSIDE, (3.BETA.,12.BETA.,16.BETA.,23S,24R,25R)-12-(ACETYLOXY)-16,23:23,26: 24,25-TRIEPOXY-9,19-CYCLOLANOSTAN-3-YL

Systematic Name

English

Code System Code Type Description

EPA CompTox

DTXSID0033388