P-COUMARIC ACID

Details

Stereochemistry	ACHIRAL
Molecular Formula	C9H8O3
Molecular Weight	164.1584
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

c1cc(ccc1/C(/[H])=C(\[H])/C(=O)O)O

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	164.1584
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

Approval Year

Targets

Primary Target	Pharmacology	Potency
Hydroxycarboxylic acid receptor 2 31 Target ID: CHEMBL3785 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19136666	Agonist 2470	310.0 µM [EC50]
Estrogen receptor beta 106 Target ID: CHEMBL242 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23608764	Agonist 2470	4.89 µM [EC50]
Aldose reductase 43 Target ID: CHEMBL1900 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18976928	Inhibitor 7728
Carbonic anhydrase II 84 Target ID: CHEMBL205 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20185318	Inhibitor 7728	0.98 µM [Ki]
Carbonic anhydrase I 59 Target ID: CHEMBL261 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20185318	Inhibitor 7728	1.07 µM [Ki]
Carbonic anhydrase VII 35 Target ID: CHEMBL2326 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20185318	Inhibitor 7728	5.23 µM [Ki]
Carbonic anhydrase IX 34 Target ID: CHEMBL3594 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20185318	Inhibitor 7728	5.33 µM [Ki]

PubMed

Title	Date	PubMed
Metabolites of orally administered Perilla frutescens extract in rats and humans.	2000 Jan	10706426
Antiviral activity of Plantago major extracts and related compounds in vitro.	2002 Jul	12076751
Dietary compounds inhibit proliferation and contraction of keloid and hypertrophic scar-derived fibroblasts in vitro: therapeutic implication for excessive scarring.	2003 Jun	12813346
Impaired mitochondrial pyruvate importation in a patient and a fetus at risk.	2003 Mar	12649063
Antioxidant and antigenotoxic effects of plant cell wall hydroxycinnamic acids in cultured HT-29 cells.	2005 Jun	15841493
Phenolic antioxidants richly contained in corn bran are slightly bioavailable in rats.	2005 Jun 15	15941352
A blend of polyphenolic compounds explains the stimulatory effect of red wine on human endothelial NO synthase.	2005 Mar	15740983
Antitubercular sterols from Thalia multiflora Horkel ex Koernicke.	2005 Oct	16261518
Modulation of hepatic phase II phenol sulfotransferase and antioxidant status by phenolic acids in rats.	2006 Aug	16443358
Involvement of p38 MAPK and Nrf2 in phenolic acid-induced P-form phenol sulfotransferase expression in human hepatoma HepG2 cells.	2006 May	16308312
Phenolic acids suppress adipocyte lipolysis via activation of the nicotinic acid receptor GPR109A (HM74a/PUMA-G).	2009 May	19136666
Biochemical mechanism of caffeic acid phenylethyl ester (CAPE) selective toxicity towards melanoma cell lines.	2010 Oct 6	20685355
In vitro antiplasmodial activity and cytotoxicity of crude extracts and compounds from the stem bark of Kigelia africana (Lam.) Benth (Bignoniaceae).	2011 Jun	21487780
Enhanced activity of antifungal drugs using natural phenolics against yeast strains of Candida and Cryptococcus.	2011 May	21332761
Interaction of cinnamic acid derivatives with commercial hypoglycemic drugs on 2-deoxyglucose uptake in 3T3-L1 adipocytes.	2011 Sep 28	21870829
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	21814840
Anti-inflammatory activity of hydroxycinnamic acid derivatives isolated from corn bran in lipopolysaccharide-stimulated Raw 264.7 macrophages.	2012 May	22366099
Sodium arsenite-induced cardiotoxicity in rats: protective role of p-coumaric acid, a common dietary polyphenol.	2013 May	23194016
Antifungal efficacy of some natural phenolic compounds against significant pathogenic and toxinogenic filamentous fungi.	2013 Oct	23800587
Sasa quelpaertensis Nakai extract and its constituent p-coumaric acid inhibit adipogenesis in 3T3-L1 cells through activation of the AMPK pathway.	2013 Sep	23810795
Modulation of gene-expression profiles associated with sodium arsenite-induced cardiotoxicity by p-coumaric acid, a common dietary polyphenol.	2014 Apr	24497207

Patents

Substance Class	Chemical Created by `admin` on `Sat Jun 26 07:27:11 UTC 2021` Edited by `admin` on `Sat Jun 26 07:27:11 UTC 2021`
Record UNII	IBS9D1EU3J
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

P-COUMARIC ACID

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-COUMARIC ACID [WHO-DD]

Common Name

English

P-HYDROXYCINNAMIC ACID

Common Name

English

4-HYDROXYCINNAMIC ACID

Systematic Name

English

HYDROXYCINNAMIC ACID

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

FDA UNII

IBS9D1EU3J