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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

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

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

Unknown
139594
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

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

Patents

EP20100187121
1
EP2438921A
1
EP2542085A4
1

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 UTC 2023
Edited
by admin
on Sat Dec 16 08:24:36 UTC 2023
Record UNII
V2P38EX6FT
Record Status Validated (UNII)
Record Version
  • Download
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
Created by admin on Sat Dec 16 08:24:36 UTC 2023 , Edited by admin on Sat Dec 16 08:24:36 UTC 2023
PRIMARY
CAS
372096-69-0
Created by admin on Sat Dec 16 08:24:36 UTC 2023 , Edited by admin on Sat Dec 16 08:24:36 UTC 2023
SUPERSEDED
EPA CompTox
DTXSID70978085
Created by admin on Sat Dec 16 08:24:36 UTC 2023 , Edited by admin on Sat Dec 16 08:24:36 UTC 2023
PRIMARY
PUBCHEM
56962372
Created by admin on Sat Dec 16 08:24:36 UTC 2023 , Edited by admin on Sat Dec 16 08:24:36 UTC 2023
PRIMARY
FDA UNII
V2P38EX6FT
Created by admin on Sat Dec 16 08:24:36 UTC 2023 , Edited by admin on Sat Dec 16 08:24:36 UTC 2023
PRIMARY
Related Record Type Details
BLACK COHOSH
PARENT -> CONSTITUENT ALWAYS PRESENT
NIH
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