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Details

Stereochemistry ABSOLUTE
Molecular Formula C35H56O9
Molecular Weight 620.8137
Optical Activity UNSPECIFIED
Defined Stereocenters 17 / 17
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CIMIRACEMOSIDE C

SMILES

[H][C@]12[C@H](C)C[C@H]3O[C@@]1(O[C@@H]3C(C)(C)O)[C@H](O)[C@@]4(C)[C@]5([H])CC[C@]6([H])[C@]7(C[C@@]57CC[C@]24C)CC[C@H](O[C@]8([H])OC[C@H](O)[C@H](O)[C@H]8O)C6(C)C

InChI

InChIKey=BTPYUWOBZFGKAI-BKJHYQRZSA-N
InChI=1S/C35H56O9/c1-17-14-19-26(30(4,5)40)44-35(43-19)25(17)31(6)12-13-34-16-33(34)11-10-22(42-27-24(38)23(37)18(36)15-41-27)29(2,3)20(33)8-9-21(34)32(31,7)28(35)39/h17-28,36-40H,8-16H2,1-7H3/t17-,18+,19-,20+,21+,22+,23+,24-,25-,26+,27+,28-,31-,32-,33-,34+,35+/m1/s1

HIDE SMILES / InChI

Molecular Formula C35H56O9
Molecular Weight 620.8137
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 16 / 17
E/Z Centers 0
Optical Activity UNSPECIFIED

CIMIRACEMOSIDE C (aka Cimifugoside M) is a triterpene glycoside which can be isolated from the roots of Cimicifuga racemosa (Black Cohosh). Despite potential toxicity, Black Cohosh continues to be consumed as a natural dietary supplement for the treatment of menopause symptoms. Cimiracemoside C has been identified as an analytical marker for the identification of Black Cohosh extract nutritional formulations. It has also been of interest as a lead compound for the treatment of diabetes in mice.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Antimalarial activity and nucleoside transport inhibitory activity of the triterpenic constituents of Cimicifuga spp.
1998 Aug
Direct analysis and identification of triterpene glycosides by LC/MS in black cohosh, Cimicifuga racemosa, and in several commercially available black cohosh products.
2000 Oct
Cimiracemosides I-P, new 9,19-cyclolanostane triterpene glycosides from Cimicifuga racemosa.
2002 Oct
Evaluation of the botanical authenticity and phytochemical profile of black cohosh products by high-performance liquid chromatography with selected ion monitoring liquid chromatography-mass spectrometry.
2006 May 3
Metabolic profiling of Actaea species extracts using high performance liquid chromatography coupled with electrospray ionization time-of-flight mass spectrometry.
2011 Mar 18
Antidiabetic effects of the Cimicifuga racemosa extract Ze 450 in vitro and in vivo in ob/ob mice.
2014 Sep 25
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Fri Dec 15 21:13:36 GMT 2023
Edited
by admin
on Fri Dec 15 21:13:36 GMT 2023
Record UNII
4DC28J6R1K
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CIMIRACEMOSIDE C
Common Name English
CIMIGENOL 3-O-.ALPHA.-L-ARABINOPYRANOSIDE
Common Name English
CIMIGENOL 3-O-.ALPHA.-L-ARABINOSIDE
Common Name English
.ALPHA.-L-ARABINOPYRANOSIDE, (3.BETA.,15.ALPHA.,16.ALPHA.,23R,24S)-16,23:16,24-DIEPOXY-15,25-DIHYDROXY-9,19-CYCLOLANOSTAN-3-YL
Common Name English
CIMICIFUGOSIDE M
Common Name English
CIMIGENOL 3-O-.ALPHA.-L-ARABINOPYRANOSIDE (CONSTITUENT OF BLACK COHOSH) [DSC]
Common Name English
CIMIGENOL-3-O-.ALPHA.-L-ARABINOSIDE
Common Name English
Code System Code Type Description
CAS
256925-92-5
Created by admin on Fri Dec 15 21:13:36 GMT 2023 , Edited by admin on Fri Dec 15 21:13:36 GMT 2023
PRIMARY
PUBCHEM
15541911
Created by admin on Fri Dec 15 21:13:36 GMT 2023 , Edited by admin on Fri Dec 15 21:13:36 GMT 2023
PRIMARY
FDA UNII
4DC28J6R1K
Created by admin on Fri Dec 15 21:13:36 GMT 2023 , Edited by admin on Fri Dec 15 21:13:36 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT