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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H20O11
Molecular Weight 448.3769
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of CIMICIFUGIC ACID B

SMILES

COC1=CC=C(\C=C\C(=O)O[C@H](C(O)=O)[C@](O)(CC2=CC=C(O)C(O)=C2)C(O)=O)C=C1O

InChI

InChIKey=YVHLLZXSGPDXOA-ZHBFVYIWSA-N
InChI=1S/C21H20O11/c1-31-16-6-3-11(8-15(16)24)4-7-17(25)32-18(19(26)27)21(30,20(28)29)10-12-2-5-13(22)14(23)9-12/h2-9,18,22-24,30H,10H2,1H3,(H,26,27)(H,28,29)/b7-4+/t18-,21-/m1/s1

HIDE SMILES / InChI
Molecular Formula C21H20O11
Molecular Weight 448.3769
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 1
Optical Activity UNSPECIFIED

Description

The potential effect of Cimicifugic acid B has being shown in preventing collagen degradation by collagenases or collagenolytic enzymes under pathological conditions, wound healing, or inflammation. Cimicifugic acid B inhibited neutrophil elastase with an IC50 of 11.4 umol/L. Cimicifugic acid B also inhibited HCT116 colon cancer cell growth.

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Activator
1430
Activator
1430
 21.0 µM [IC50]
Inhibitor
8297
 11.4 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Basic research
Unknown

Approved Use

Unknown
Primary
Basic research
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Effects of fukinolic acid and cimicifugic acids from Cimicifuga species on collagenolytic activity.
2001 Oct
Patents

Patents

US20060216251
1
US20150150770
1
US7776915
2

Sample Use Guides

In Vivo Use Guide
Curator's Comment: Cimicifuga racemosa (black cohosh) contains cimicifugic acid B.
Menopause Support: There is no proven effective dose for black cohosh. The British Herbal Compendium recommends 40-200 milligrams of dried rhizome daily in divided doses, although traditional doses have been as high as 1-2 grams three times daily.
Route of Administration: Oral
In Vitro Use Guide
Cimicifugic acid B inhibited HCT116 colon cancer cell growth in vitro with the IC50 concentration of 12.42 uM.
Substance Class Chemical
Created
by admin
on Fri Dec 15 22:05:50 UTC 2023
Edited
by admin
on Fri Dec 15 22:05:50 UTC 2023
Record UNII
RMQ0SKL6CI
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CIMICIFUGIC ACID B
Common Name English
BUTANEDIOIC ACID, 2-((3,4-DIHYDROXYPHENYL)METHYL)-2-HYDROXY-3-(((2E)-3-(3-HYDROXY-4-METHOXYPHENYL)-1-OXO-2-PROPEN-1-YL)OXY)-, (2R,3S)-
Systematic Name English
BUTANEDIOIC ACID, 2-((3,4-DIHYDROXYPHENYL)METHYL)-2-HYDROXY-3-((3-(3-HYDROXY-4-METHOXYPHENYL)-1-OXO-2-PROPENYL)OXY)-, (S-(R*,S*-(E)))-
Systematic Name English
BUTANEDIOIC ACID, 2-9(3,4-DIHYDROXYPHENYL)METHYL)-2-HYDROXY-3-(((2E)-3-(3-HYDROXY-4-METHOXYPHENYL)-1-OXO-2-PROPENYL)OXY)-, (2R,3S)-
Systematic Name English
CIMICIFUGA ACID B
Common Name English
BUTANEDIOIC ACID, 2-9(3,4-DIHYDROXYPHENYL)METHYL)-2-HYDROXY-3-((3-(3-HYDROXY-4-METHOXYPHENYL)-1-OXO-2-PROPENYL)OXY)-, (S-(R*,S*(E)))-
Systematic Name English
Code System Code Type Description
PUBCHEM
6449880
Created by admin on Fri Dec 15 22:05:50 UTC 2023 , Edited by admin on Fri Dec 15 22:05:50 UTC 2023
PRIMARY
CAS
205114-66-5
Created by admin on Fri Dec 15 22:05:50 UTC 2023 , Edited by admin on Fri Dec 15 22:05:50 UTC 2023
PRIMARY
FDA UNII
RMQ0SKL6CI
Created by admin on Fri Dec 15 22:05:50 UTC 2023 , Edited by admin on Fri Dec 15 22:05:50 UTC 2023
PRIMARY
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