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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
503
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2752
 310.0 µM [EC50]
Agonist
2752
 4.89 µM [EC50]
Inhibitor
8504
Inhibitor
8504
 0.98 µM [Ki]
Inhibitor
8504
 1.07 µM [Ki]
Inhibitor
8504
 5.23 µM [Ki]
Inhibitor
8504
 5.33 µM [Ki]
PubMed

PubMed

TitleDatePubMed
Modulation of gene-expression profiles associated with sodium arsenite-induced cardiotoxicity by p-coumaric acid, a common dietary polyphenol.
2014-04
Antifungal efficacy of some natural phenolic compounds against significant pathogenic and toxinogenic filamentous fungi.
2013-10
Sasa quelpaertensis Nakai extract and its constituent p-coumaric acid inhibit adipogenesis in 3T3-L1 cells through activation of the AMPK pathway.
2013-09
Sodium arsenite-induced cardiotoxicity in rats: protective role of p-coumaric acid, a common dietary polyphenol.
2013-05
Anti-inflammatory activity of hydroxycinnamic acid derivatives isolated from corn bran in lipopolysaccharide-stimulated Raw 264.7 macrophages.
2012-05
Antimalarial drug interactions of compounds isolated from Kigelia africana (Bignoniaceae) and their synergism with artemether, against the multidrug-resistant W2mef Plasmodium falciparum strain.
2012-02
Interaction of cinnamic acid derivatives with commercial hypoglycemic drugs on 2-deoxyglucose uptake in 3T3-L1 adipocytes.
2011-09-28
In vitro antiplasmodial activity and cytotoxicity of crude extracts and compounds from the stem bark of Kigelia africana (Lam.) Benth (Bignoniaceae).
2011-06
Enhanced activity of antifungal drugs using natural phenolics against yeast strains of Candida and Cryptococcus.
2011-05
Biochemical mechanism of caffeic acid phenylethyl ester (CAPE) selective toxicity towards melanoma cell lines.
2010-10-06
Phenolic acids suppress adipocyte lipolysis via activation of the nicotinic acid receptor GPR109A (HM74a/PUMA-G).
2009-05
Modulation of hepatic phase II phenol sulfotransferase and antioxidant status by phenolic acids in rats.
2006-08
Involvement of p38 MAPK and Nrf2 in phenolic acid-induced P-form phenol sulfotransferase expression in human hepatoma HepG2 cells.
2006-05
Antitubercular sterols from Thalia multiflora Horkel ex Koernicke.
2005-10
Phenolic antioxidants richly contained in corn bran are slightly bioavailable in rats.
2005-06-15
Antioxidant and antigenotoxic effects of plant cell wall hydroxycinnamic acids in cultured HT-29 cells.
2005-06
A blend of polyphenolic compounds explains the stimulatory effect of red wine on human endothelial NO synthase.
2005-03
Dietary compounds inhibit proliferation and contraction of keloid and hypertrophic scar-derived fibroblasts in vitro: therapeutic implication for excessive scarring.
2003-06
Impaired mitochondrial pyruvate importation in a patient and a fetus at risk.
2003-03
Antiviral activity of Plantago major extracts and related compounds in vitro.
2002-07
Metabolites of orally administered Perilla frutescens extract in rats and humans.
2000-01
Patents

Patents

03998851
1
06833421
3
JP2000247900A
4
JP2000319154A
18
JP2002003385A
1
JP2002012535A
6
JP2002145719A
1
JP2002512267A
4
JP2002524505A
3
JP2002541233A
406
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 Mon Mar 31 19:18:46 GMT 2025
Edited
by admin
on Mon Mar 31 19:18:46 GMT 2025
Record UNII
IBS9D1EU3J
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
P-COUMARIC ACID
MI   WHO-DD  
Common Name English
HYDROXYCINNAMIC ACID
INCI  
INCI  
Preferred 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
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
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 Mon Mar 31 19:18:46 GMT 2025 , Edited by admin on Mon Mar 31 19:18:46 GMT 2025
PRIMARY
FDA UNII
IBS9D1EU3J
Created by admin on Mon Mar 31 19:18:46 GMT 2025 , Edited by admin on Mon Mar 31 19:18:46 GMT 2025
PRIMARY
SMS_ID
100000089731
Created by admin on Mon Mar 31 19:18:46 GMT 2025 , Edited by admin on Mon Mar 31 19:18:46 GMT 2025
PRIMARY
CAS
501-98-4
Created by admin on Mon Mar 31 19:18:46 GMT 2025 , Edited by admin on Mon Mar 31 19:18:46 GMT 2025
PRIMARY
CAS
7400-08-0
Created by admin on Mon Mar 31 19:18:46 GMT 2025 , Edited by admin on Mon Mar 31 19:18:46 GMT 2025
NON-SPECIFIC STEREOCHEMISTRY
PUBCHEM
637542
Created by admin on Mon Mar 31 19:18:46 GMT 2025 , Edited by admin on Mon Mar 31 19:18:46 GMT 2025
PRIMARY
WIKIPEDIA
p-Coumaric acid
Created by admin on Mon Mar 31 19:18:46 GMT 2025 , Edited by admin on Mon Mar 31 19:18:46 GMT 2025
PRIMARY
CHEBI
36090
Created by admin on Mon Mar 31 19:18:46 GMT 2025 , Edited by admin on Mon Mar 31 19:18:46 GMT 2025
PRIMARY
MERCK INDEX
m3818
Created by admin on Mon Mar 31 19:18:46 GMT 2025 , Edited by admin on Mon Mar 31 19:18:46 GMT 2025
PRIMARY Merck Index
RXCUI
1485787
Created by admin on Mon Mar 31 19:18:46 GMT 2025 , Edited by admin on Mon Mar 31 19:18:46 GMT 2025
PRIMARY RxNorm
CHEBI
23401
Created by admin on Mon Mar 31 19:18:46 GMT 2025 , Edited by admin on Mon Mar 31 19:18:46 GMT 2025
PRIMARY
DAILYMED
IBS9D1EU3J
Created by admin on Mon Mar 31 19:18:46 GMT 2025 , Edited by admin on Mon Mar 31 19:18:46 GMT 2025
PRIMARY
EVMPD
SUB14773MIG
Created by admin on Mon Mar 31 19:18:46 GMT 2025 , Edited by admin on Mon Mar 31 19:18:46 GMT 2025
PRIMARY
MESH
C032171
Created by admin on Mon Mar 31 19:18:46 GMT 2025 , Edited by admin on Mon Mar 31 19:18:46 GMT 2025
PRIMARY
NSC
674321
Created by admin on Mon Mar 31 19:18:46 GMT 2025 , Edited by admin on Mon Mar 31 19:18:46 GMT 2025
PRIMARY
EPA CompTox
DTXSID30901076
Created by admin on Mon Mar 31 19:18:46 GMT 2025 , Edited by admin on Mon Mar 31 19:18:46 GMT 2025
PRIMARY
DRUG BANK
DB04066
Created by admin on Mon Mar 31 19:18:46 GMT 2025 , Edited by admin on Mon Mar 31 19:18:46 GMT 2025
PRIMARY
ECHA (EC/EINECS)
231-000-0
Created by admin on Mon Mar 31 19:18:46 GMT 2025 , Edited by admin on Mon Mar 31 19:18:46 GMT 2025
PRIMARY
NSC
59260
Created by admin on Mon Mar 31 19:18:46 GMT 2025 , Edited by admin on Mon Mar 31 19:18:46 GMT 2025
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 REBAUDIANA 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.
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VACCINIUM MYRTILLUS LEAF
PARENT -> CONSTITUENT ALWAYS PRESENT
GALIUM APARINE WHOLE
PARENT -> CONSTITUENT ALWAYS PRESENT
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PARENT -> CONSTITUENT ALWAYS PRESENT
CENTAURIUM ERYTHRAEA WHOLE
PARENT -> CONSTITUENT ALWAYS PRESENT
NIH
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