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

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

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 2578

PubMed

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

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 `Sat Dec 16 08:24:36 GMT 2023` Edited by `admin` on `Sat Dec 16 08:24:36 GMT 2023`
Record UNII	V2P38EX6FT
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

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

Common Name

English

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

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