23-O-ACETYLSHENGMANOL-3-O-.BETA.-D-XYLOPYRANOSIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C37H58O10
Molecular Weight	662.8504
Optical Activity	UNSPECIFIED
Defined Stereocenters	16 / 16
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of 23-O-ACETYLSHENGMANOL-3-O-.BETA.-D-XYLOPYRANOSIDE

Structure Search

SMILES

C[C@H](C[C@@H](OC(C)=O)[C@@H]1OC1(C)C)[C@H]2C(=O)[C@H](O)[C@@]3(C)[C@@H]4CC[C@@H]5[C@]6(C[C@@]46CC[C@]23C)CC[C@H](O[C@@H]7OC[C@@H](O)[C@H](O)[C@H]7O)C5(C)C

InChI

InChIKey=IHEJMZHKJYHVFF-JUKRZFGDSA-N

InChI=1S/C37H58O10/c1-18(15-21(45-19(2)38)30-33(5,6)47-30)25-27(41)29(43)35(8)23-10-9-22-32(3,4)24(46-31-28(42)26(40)20(39)16-44-31)11-12-36(22)17-37(23,36)14-13-34(25,35)7/h18,20-26,28-31,39-40,42-43H,9-17H2,1-8H3/t18-,20-,21-,22+,23+,24+,25+,26+,28-,29+,30+,31+,34-,35-,36-,37+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C37H58O10
Molecular Weight	662.8504
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	16 / 16
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.chemspider.com/Chemical-Structure.9040544.html/18cc093d-256f-48a7-b70d-7c002e4f23df | https://www.ncbi.nlm.nih.gov/pubmed/21082802 | https://www.ncbi.nlm.nih.gov/pubmed/12398548

23-O-Acetylshengmanol-3-O-D-Xyloside is a natural product which can be extracted from Actaea racemosa (Black cohosh). It is structurally similar to 23-O-Acetylshengmanol-3-O-α-L-Arabinoside, except that beta-D-xyloside is substituted in place of α-L-Arabinoside. 23-O-Acetylshengmanol-3-OD-Xyloside is a potent enhancer of GABA-induced chloride currents.

Originator

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596

PubMed

Title	Date	PubMed
Bioactivity-guided isolation of GABA(A) receptor modulating constituents from the rhizomes of Actaea racemosa.	2010-12-27	21082802
Two new cyclolanostanol xylosides from the aerial parts of Cimicifuga dahurica.	2002-10	12398548

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

GABA(A) receptors, were expressed in Xenopus laevis oocytes, and GABA-induced chloride current (I-GABA) was measured using the two-microelectrode voltage clamp technique. 23-O-acetylshengmanol 3-O-β-d-xylopyranoside (100 microM) enhanced I-GABA by 1692 +/- 201%.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 22:03:28 GMT 2025` Edited by `admin` on `Mon Mar 31 22:03:28 GMT 2025`
Record UNII	V2P38EX6FT
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

23-O-ACETYLSHENGMANOL-3-O-.BETA.-D-XYLOPYRANOSIDE (CONSTITUENT OF BLACK COHOSH) [DSC]

Preferred Name

English

23-O-ACETYLSHENGMANOL-3-O-.BETA.-D-XYLOPYRANOSIDE

Common Name

English

23-O-ACETYLSHENGMANOL-3-O-D-XYLOSIDE

Common Name

English

9,19-CYCLOLANOSTAN-16-ONE, 23-(ACETYLOXY)-24,25-EPOXY-15-HYDROXY-3-(.BETA.-D-XYLOPYRANOSYLOXY)-, (3.BETA.,15.ALPHA.,23R,24R)-

Systematic Name

English

Code System Code Type Description

CAS

62498-88-8