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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 of CIMIRACEMOSIDE N

SMILES

C[C@@H]1C[C@]2(OC[C@]3(C)O[C@H]23)O[C@H]4C[C@@]5(C)[C@@H]6CC[C@@H]7[C@]8(C[C@@]68C[C@@H](OC(C)=O)[C@]5(C)[C@@H]14)CC[C@H](O[C@@H]9OC[C@H](O)[C@H](O)[C@H]9O)C7(C)C

InChI

InChIKey=GCMGJWLOGKSUGX-GVGYZBMQSA-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 18 / 18
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

cimiracemoside N is a triterpene glycoside which can be isolated from the roots of Cimicifuga racemosa (Black Cohosh). Black Cohosh is consumed as a natural dietary supplement for the treatment of menopause symptoms.

Originator

University of Illinois
6
Curator's Comment: Collaborative Research in the Pharmaceutical Sciences (PCRPS, M/C 877), and UIC/ NIH Center for Botanical Dietary Supplements Research,

Approval Year

Unknown
149124
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Black cohosh (Cimicifuga spp.) for menopausal symptoms.
2012-09-12
Cimiracemosides I-P, new 9,19-cyclolanostane triterpene glycosides from Cimicifuga racemosa.
2002-10

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Curator's Comment: Related cimiracemosides (A-H) were found to modulate GABA induced currents through GABA-A ion channel, but cimiracemoside D (compound 7) was not tested / not active in this assay. (https://www.ncbi.nlm.nih.gov/pubmed/21082802)
Unknown
Substance Class Chemical
Created
by admin
on Mon Mar 31 23:29:08 GMT 2025
Edited
by admin
on Mon Mar 31 23:29:08 GMT 2025
Record UNII
9259Y53BCI
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CIMIRACEMOSIDE N
Common Name English
CIMIRACEMOSIDE N, (-)-
Preferred Name English
.ALPHA.-L-ARABINOPYRANOSIDE, (3.BETA.,12.BETA.,16.BETA.,23S,24S,25S)-12-(ACETYLOXY)-16,23:23,26:24,25-TRIEPOXY-9,19-CYCLOLANOSTAN-3-YL
Systematic Name English
Code System Code Type Description
CAS
473554-78-8
Created by admin on Mon Mar 31 23:29:08 GMT 2025 , Edited by admin on Mon Mar 31 23:29:08 GMT 2025
PRIMARY
PUBCHEM
21591918
Created by admin on Mon Mar 31 23:29:08 GMT 2025 , Edited by admin on Mon Mar 31 23:29:08 GMT 2025
PRIMARY
FDA UNII
9259Y53BCI
Created by admin on Mon Mar 31 23:29:08 GMT 2025 , Edited by admin on Mon Mar 31 23:29:08 GMT 2025
PRIMARY
Related Record Type Details
BLACK COHOSH
PARENT -> CONSTITUENT ALWAYS PRESENT
NIH
NCATS
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