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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H20O11
Molecular Weight 448.3777
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of CIMICIFUGIC ACID B

SMILES

COc1ccc(/C(/[H])=C(\[H])/C(=O)O[C@]([H])(C(=O)O)[C@](Cc2ccc(c(c2)O)O)(C(=O)O)O)cc1O

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 448.3777
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 1
Optical Activity UNSPECIFIED

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

Targets

Targets

Primary TargetPharmacologyConditionPotency
21.0 µM [IC50]
11.4 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Effects of fukinolic acid and cimicifugic acids from Cimicifuga species on collagenolytic activity.
2001 Oct
Cytotoxic caffeic acid derivatives from the rhizomes of Cimicifuga heracleifolia.
2012 Sep
Patents

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
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 Jun 25 23:11:06 UTC 2021
Edited
by admin
on Fri Jun 25 23:11:06 UTC 2021
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 Jun 25 23:11:06 UTC 2021 , Edited by admin on Fri Jun 25 23:11:06 UTC 2021
PRIMARY
CAS
205114-66-5
Created by admin on Fri Jun 25 23:11:06 UTC 2021 , Edited by admin on Fri Jun 25 23:11:06 UTC 2021
PRIMARY
FDA UNII
RMQ0SKL6CI
Created by admin on Fri Jun 25 23:11:06 UTC 2021 , Edited by admin on Fri Jun 25 23:11:06 UTC 2021
PRIMARY
Related Record Type Details
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