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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
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 GMT 2023
Edited
by admin
on Fri Dec 15 22:05:50 GMT 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 GMT 2023 , Edited by admin on Fri Dec 15 22:05:50 GMT 2023
PRIMARY
CAS
205114-66-5
Created by admin on Fri Dec 15 22:05:50 GMT 2023 , Edited by admin on Fri Dec 15 22:05:50 GMT 2023
PRIMARY
FDA UNII
RMQ0SKL6CI
Created by admin on Fri Dec 15 22:05:50 GMT 2023 , Edited by admin on Fri Dec 15 22:05:50 GMT 2023
PRIMARY
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