CIMICIFUGIC ACID B

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 Search

SMILES

COC1=C(O)C=C(\C=C\C(=O)O[C@H](C(O)=O)[C@](O)(CC2=CC(O)=C(O)C=C2)C(O)=O)C=C1

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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11642333 | https://www.ncbi.nlm.nih.gov/pubmed/11199135 | https://www.ncbi.nlm.nih.gov/pubmed/23054712

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

Primary Target	Pharmacology	Potency
Apoptosis 156 Target ID: map04210 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23054712	Activator 1447
Radical scavenging activity 12 Target ID: CHEMBL613712 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12428954	Activator 1447	21.0 µM [IC50]
Leukocyte elastase 19 Target ID: CHEMBL248 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11199135	Inhibitor 8504	11.4 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cancer 609 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23054712	Primary		Basic research	Unknown Approved Use Unknown
Wounds 16 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11642333	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Cytotoxic caffeic acid derivatives from the rhizomes of Cimicifuga heracleifolia.	2012-09	23054712
Effects of fukinolic acid and cimicifugic acids from Cimicifuga species on collagenolytic activity.	2001-10	11642333

Patents

Sample Use Guides

In Vivo Use Guide

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 `Mon Mar 31 20:23:31 GMT 2025` Edited by `admin` on `Mon Mar 31 20:23:31 GMT 2025`
Record UNII	RMQ0SKL6CI
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CIMICIFUGA ACID B

Preferred Name

English

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

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 Mon Mar 31 20:23:31 GMT 2025 , Edited by admin on Mon Mar 31 20:23:31 GMT 2025

PRIMARY

CAS

205114-66-5

Created by admin on Mon Mar 31 20:23:31 GMT 2025 , Edited by admin on Mon Mar 31 20:23:31 GMT 2025

PRIMARY

EPA CompTox

DTXSID801347722

Created by admin on Mon Mar 31 20:23:31 GMT 2025 , Edited by admin on Mon Mar 31 20:23:31 GMT 2025

PRIMARY

FDA UNII

RMQ0SKL6CI

Created by admin on Mon Mar 31 20:23:31 GMT 2025 , Edited by admin on Mon Mar 31 20:23:31 GMT 2025

PRIMARY

Related Record Type Details


					K73E24S6X9

BLACK COHOSH

PARENT -> CONSTITUENT ALWAYS PRESENT

Details

SMILES

InChI

DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/11642333 | https://www.ncbi.nlm.nih.gov/pubmed/11199135 | https://www.ncbi.nlm.nih.gov/pubmed/23054712

Approval Year

Targets

Conditions

Approved Use

Approved Use

PubMed

Patents

Sample Use Guides

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11642333 | https://www.ncbi.nlm.nih.gov/pubmed/11199135 | https://www.ncbi.nlm.nih.gov/pubmed/23054712