CAFFEIC ACID PHENETHYL ESTER

Details

Stereochemistry	ACHIRAL
Molecular Formula	C17H16O4
Molecular Weight	284.3065
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure of CAFFEIC ACID PHENETHYL ESTER

Structure Search

SMILES

OC1=C(O)C=C(\C=C\C(=O)OCCC2=CC=CC=C2)C=C1

InChI

InChIKey=SWUARLUWKZWEBQ-VQHVLOKHSA-N

InChI=1S/C17H16O4/c18-15-8-6-14(12-16(15)19)7-9-17(20)21-11-10-13-4-2-1-3-5-13/h1-9,12,18-19H,10-11H2/b9-7+

HIDE SMILES / InChI

Approval Year

Targets

Primary Target	Pharmacology	Potency
Aldo-keto reductase family 1 member B10 7 Target ID: CHEMBL5983 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22236472	Inhibitor 8297	80.0 nM [IC50]
Aldo-keto-reductase family 1 member C3 9 Target ID: CHEMBL4681 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22506594	Inhibitor 8297	1.7 µM [IC50]
Human immunodeficiency virus type 1 integrase 19 Target ID: CHEMBL3471 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7473544	Inhibitor 8297	7.0 µM [IC50]
Arachidonate 5-lipoxygenase 49 Target ID: CHEMBL215 Sources: https://www.ncbi.nlm.nih.gov/pubmed/29953727	Inhibitor 8297	1.01 µM [IC50]
Apoptosis 155 Target ID: map04210 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28926932	Activator 1430	27.84 µM [IC50]

PubMed

Title	Date	PubMed
Inhibitors of human immunodeficiency virus integrase.	1993 Mar 15	8460151
Hydroxylated aromatic inhibitors of HIV-1 integrase.	1995 Oct 13	7473544
Colon cancer chemopreventive drugs modulate integrin-mediated signaling pathways.	2000 Mar	10741720
Caffeic acid phenethyl ester-induced PC-3 cell apoptosis is caspase-dependent and mediated through the loss of inhibitors of apoptosis proteins.	2004 Aug	15291876
Design and synthesis of novel dihydroxyindole-2-carboxylic acids as HIV-1 integrase inhibitors.	2004 Mar	15185725
IL-1beta regulates expression of Cx32, occludin, and claudin-2 of rat hepatocytes via distinct signal transduction pathways.	2004 Oct 1	15350541
PAR1-mediated NFkappaB activation promotes survival of prostate cancer cells through a Bcl-xL-dependent mechanism.	2005 Oct 15	16052512
Enhancement of caffeic acid phenethyl ester on all-trans retinoic acid-induced differentiation in human leukemia HL-60 cells.	2006 Oct 1	16766008
Protective effect of caffeic acid phenethyl ester against carbon tetrachloride-induced hepatotoxicity in mice.	2008 Jun 3	18436364
An approach to the study of gene expression in hepatocarcinogenesis initiation.	2010 Apr	20360939
p52-Bcl3 complex promotes cyclin D1 expression in BEAS-2B cells in response to low concentration arsenite.	2010 Jun 29	20420878
Cytotoxicity of arsenic trioxide is enhanced by (-)-epigallocatechin-3-gallate via suppression of ferritin in cancer cells.	2011 Jan 1	20950636
The metabolic bioactivation of caffeic acid phenethyl ester (CAPE) mediated by tyrosinase selectively inhibits glutathione S-transferase.	2011 Jul 15	21458432
A pharmacologically-based array to identify targets of cyclosporine A-induced toxicity in cultured renal proximal tubule cells.	2012 Jan 15	22155090
Arsenic augments the uptake of oxidized LDL by upregulating the expression of lectin-like oxidized LDL receptor in mouse aortic endothelial cells.	2013 Dec 15	24145059
Cytotoxic and apoptotic effects of leptocarpin, a plant-derived sesquiterpene lactone, on human cancer cell lines.	2015 Dec 5	26562779

Name

Type

Language

CAFFEIC ACID PHENETHYL ESTER

Common Name

English

PHENETHYL CAFFEATE [INCI]

Common Name

English

PHENETHYL CAFFEATE

Official Name

English

Classification Tree Code System Code

DSLD

3202 (Number of products:3)