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Details

Stereochemistry ACHIRAL
Molecular Formula C9H8O3
Molecular Weight 164.158
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of P-COUMARIC ACID

SMILES

OC(=O)\C=C\C1=CC=C(O)C=C1

InChI

InChIKey=NGSWKAQJJWESNS-ZZXKWVIFSA-N
InChI=1S/C9H8O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-6,10H,(H,11,12)/b6-3+

HIDE SMILES / InChI
Molecular Formula C9H8O3
Molecular Weight 164.158
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Approval Year

2014
494
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2678
 310.0 µM [EC50]
Agonist
2678
 4.89 µM [EC50]
Inhibitor
8297
Inhibitor
8297
 0.98 µM [Ki]
Inhibitor
8297
 1.07 µM [Ki]
Inhibitor
8297
 5.23 µM [Ki]
Inhibitor
8297
 5.33 µM [Ki]
PubMed

PubMed

TitleDatePubMed
Metabolites of orally administered Perilla frutescens extract in rats and humans.
2000 Jan
Antiviral activity of Plantago major extracts and related compounds in vitro.
2002 Jul
Dietary compounds inhibit proliferation and contraction of keloid and hypertrophic scar-derived fibroblasts in vitro: therapeutic implication for excessive scarring.
2003 Jun
Impaired mitochondrial pyruvate importation in a patient and a fetus at risk.
2003 Mar
Antioxidant and antigenotoxic effects of plant cell wall hydroxycinnamic acids in cultured HT-29 cells.
2005 Jun
Phenolic antioxidants richly contained in corn bran are slightly bioavailable in rats.
2005 Jun 15
A blend of polyphenolic compounds explains the stimulatory effect of red wine on human endothelial NO synthase.
2005 Mar
Antitubercular sterols from Thalia multiflora Horkel ex Koernicke.
2005 Oct
Modulation of hepatic phase II phenol sulfotransferase and antioxidant status by phenolic acids in rats.
2006 Aug
Involvement of p38 MAPK and Nrf2 in phenolic acid-induced P-form phenol sulfotransferase expression in human hepatoma HepG2 cells.
2006 May
Phenolic acids suppress adipocyte lipolysis via activation of the nicotinic acid receptor GPR109A (HM74a/PUMA-G).
2009 May
Biochemical mechanism of caffeic acid phenylethyl ester (CAPE) selective toxicity towards melanoma cell lines.
2010 Oct 6
In vitro antiplasmodial activity and cytotoxicity of crude extracts and compounds from the stem bark of Kigelia africana (Lam.) Benth (Bignoniaceae).
2011 Jun
Enhanced activity of antifungal drugs using natural phenolics against yeast strains of Candida and Cryptococcus.
2011 May
Interaction of cinnamic acid derivatives with commercial hypoglycemic drugs on 2-deoxyglucose uptake in 3T3-L1 adipocytes.
2011 Sep 28
Antimalarial drug interactions of compounds isolated from Kigelia africana (Bignoniaceae) and their synergism with artemether, against the multidrug-resistant W2mef Plasmodium falciparum strain.
2012 Feb
Anti-inflammatory activity of hydroxycinnamic acid derivatives isolated from corn bran in lipopolysaccharide-stimulated Raw 264.7 macrophages.
2012 May
Sodium arsenite-induced cardiotoxicity in rats: protective role of p-coumaric acid, a common dietary polyphenol.
2013 May
Antifungal efficacy of some natural phenolic compounds against significant pathogenic and toxinogenic filamentous fungi.
2013 Oct
Sasa quelpaertensis Nakai extract and its constituent p-coumaric acid inhibit adipogenesis in 3T3-L1 cells through activation of the AMPK pathway.
2013 Sep
Modulation of gene-expression profiles associated with sodium arsenite-induced cardiotoxicity by p-coumaric acid, a common dietary polyphenol.
2014 Apr
Patents

Patents

03998851
1
06833421
3
JP2000247900A
4
JP2000319154A
18
JP2002003385A
1
JP2002012535A
6
JP2002145719A
1
JP2002512267A
4
JP2002524505A
3
JP2002541233A
400
JP2002544546A
1
JP2003146806A
1
JP2003525103A
5
JP2004161706A
3
JP2005058096A
1
JP2005089676A
2
JP2005126412A
1
JP2007236222A
1
JP2008189554A
1
JP2009161484A
1
JP2009161485A
2
JP2009173670A
1
JP2014196256A
1
JP3267615B2
1
JP4764416B2
3
JPH02129149A
1
JPH02256601A
3
JPH0314596A
1
JPH04266807A
1
JPH04270298A
1
JPH05117125A
2
JPH08239661A
2
JPH09286728A
1
JPH09328424A
2
JPH10117679A
1
JPH10117680A
4
JPH10262547A
2
JPH10338603A
1
JPH11106335A
2
Substance Class Chemical
Created
by admin
on Fri Dec 15 18:40:45 UTC 2023
Edited
by admin
on Fri Dec 15 18:40:45 UTC 2023
Record UNII
IBS9D1EU3J
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
P-COUMARIC ACID
MI   WHO-DD  
Common Name English
P-coumaric acid [WHO-DD]
Common Name English
P-COUMARIC ACID [MI]
Common Name English
NSC-674321
Code English
NSC-59260
Code English
(E)-P-COUMARIC ACID
Common Name English
PARAHYDROXYCINNAMIC ACID
Systematic Name English
2-PROPENOIC ACID, 3-(4-HYDROXYPHENYL)-
Common Name English
CINNAMIC ACID, P-HYDROXY-
Common Name English
CINNAMIC ACID, P-HYDROXY-, (E)-
Common Name English
PARA HYDROXYCINNAMIC ACID
Systematic Name English
P-HYDROXYCINNAMIC ACID
Common Name English
4-HYDROXYCINNAMIC ACID
Systematic Name English
HYDROXYCINNAMIC ACID
INCI  
INCI  
Official Name English
3-(4-HYDROXYPHENYL)-2-PROPENOIC ACID
Systematic Name English
ORISTAR PCA
Brand Name English
2-PROPENOIC ACID, 3-(4-HYDROXYPHENYL)-, (E)-
Common Name English
TRANS-P-COUMARIC ACID
Common Name English
.BETA.-(4-HYDROXYPHENYL)ACRYLIC ACID
Systematic Name English
4-COUMARIC ACID
Common Name English
HYDROXYCINNAMIC ACID [INCI]
Common Name English
2-PROPENOIC ACID, 3-(4-HYDROXYPHENYL)-, (2E)-
Common Name English
NARINGENINIC ACID
Common Name English
Code System Code Type Description
CHEBI
32374
Created by admin on Fri Dec 15 18:40:45 UTC 2023 , Edited by admin on Fri Dec 15 18:40:45 UTC 2023
PRIMARY
FDA UNII
IBS9D1EU3J
Created by admin on Fri Dec 15 18:40:45 UTC 2023 , Edited by admin on Fri Dec 15 18:40:45 UTC 2023
PRIMARY
SMS_ID
100000089731
Created by admin on Fri Dec 15 18:40:45 UTC 2023 , Edited by admin on Fri Dec 15 18:40:45 UTC 2023
PRIMARY
CAS
501-98-4
Created by admin on Fri Dec 15 18:40:45 UTC 2023 , Edited by admin on Fri Dec 15 18:40:45 UTC 2023
PRIMARY
CAS
7400-08-0
Created by admin on Fri Dec 15 18:40:45 UTC 2023 , Edited by admin on Fri Dec 15 18:40:45 UTC 2023
NON-SPECIFIC STEREOCHEMISTRY
PUBCHEM
637542
Created by admin on Fri Dec 15 18:40:45 UTC 2023 , Edited by admin on Fri Dec 15 18:40:45 UTC 2023
PRIMARY
WIKIPEDIA
p-Coumaric acid
Created by admin on Fri Dec 15 18:40:45 UTC 2023 , Edited by admin on Fri Dec 15 18:40:45 UTC 2023
PRIMARY
CHEBI
36090
Created by admin on Fri Dec 15 18:40:45 UTC 2023 , Edited by admin on Fri Dec 15 18:40:45 UTC 2023
PRIMARY
MERCK INDEX
m3818
Created by admin on Fri Dec 15 18:40:45 UTC 2023 , Edited by admin on Fri Dec 15 18:40:45 UTC 2023
PRIMARY Merck Index
RXCUI
1485787
Created by admin on Fri Dec 15 18:40:45 UTC 2023 , Edited by admin on Fri Dec 15 18:40:45 UTC 2023
PRIMARY RxNorm
CHEBI
23401
Created by admin on Fri Dec 15 18:40:45 UTC 2023 , Edited by admin on Fri Dec 15 18:40:45 UTC 2023
PRIMARY
DAILYMED
IBS9D1EU3J
Created by admin on Fri Dec 15 18:40:45 UTC 2023 , Edited by admin on Fri Dec 15 18:40:45 UTC 2023
PRIMARY
EVMPD
SUB14773MIG
Created by admin on Fri Dec 15 18:40:45 UTC 2023 , Edited by admin on Fri Dec 15 18:40:45 UTC 2023
PRIMARY
MESH
C032171
Created by admin on Fri Dec 15 18:40:45 UTC 2023 , Edited by admin on Fri Dec 15 18:40:45 UTC 2023
PRIMARY
NSC
674321
Created by admin on Fri Dec 15 18:40:45 UTC 2023 , Edited by admin on Fri Dec 15 18:40:45 UTC 2023
PRIMARY
DRUG BANK
DB04066
Created by admin on Fri Dec 15 18:40:45 UTC 2023 , Edited by admin on Fri Dec 15 18:40:45 UTC 2023
PRIMARY
ECHA (EC/EINECS)
231-000-0
Created by admin on Fri Dec 15 18:40:45 UTC 2023 , Edited by admin on Fri Dec 15 18:40:45 UTC 2023
PRIMARY
NSC
59260
Created by admin on Fri Dec 15 18:40:45 UTC 2023 , Edited by admin on Fri Dec 15 18:40:45 UTC 2023
PRIMARY
Related Record Type Details
IPOMOEA AQUATICA LEAF
PARENT -> CONSTITUENT ALWAYS PRESENT
50.8% reaction on PG synthase w/10.0 mM conc. of compound
STEVIA REBAUDIUNA LEAF
PARENT -> CONSTITUENT ALWAYS PRESENT
p-Coumaric acid content for water extract of plant leaf was 30.47+/-0.36 and plant callus was 1.81+/-0.41 expressed as mg/100 g of dry base of extract. For the analysis of phenolic acids, a Nova pack C18 UG120 equipped with a Guard column, a JASCO HPLC system consisting of a column oven, a UV-Vis diode array detector set at 280 nm, a Liquid chromatography pump and a ChromNAV software program were used.
BLACK COHOSH
PARENT -> CONSTITUENT ALWAYS PRESENT
VACCINIUM MYRTILLUS LEAF
PARENT -> CONSTITUENT ALWAYS PRESENT
GALIUM APARINE WHOLE
PARENT -> CONSTITUENT ALWAYS PRESENT
LYCIUM BARBARUM FRUIT
PARENT -> CONSTITUENT ALWAYS PRESENT
CENTAURIUM ERYTHRAEA WHOLE
PARENT -> CONSTITUENT ALWAYS PRESENT
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