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

Molecular Formula	C17H16O4
Molecular Weight	284.3065
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
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
Inhibition of HIV-1 integrase by flavones, caffeic acid phenethyl ester (CAPE) and related compounds.	1994 Aug 3	7520698
Hydroxylated aromatic inhibitors of HIV-1 integrase.	1995 Oct 13	7473544
HIV-1 integrase pharmacophore: discovery of inhibitors through three-dimensional database searching.	1997 Mar 14	9083480
Colon cancer chemopreventive drugs modulate integrin-mediated signaling pathways.	2000 Mar	10741720
Caffeic acid phenethyl ester as a protective agent against doxorubicin nephrotoxicity in rats.	2004 Oct	15369732
Inhibition of multidrug resistance proteins MRP1 and MRP2 by a series of alpha,beta-unsaturated carbonyl compounds.	2005 Jun 15	15885658
The activity of adenosine deaminase and the level of nitric oxide in spinal cord of methotrexate administered rats: protective effect of caffeic acid phenethyl ester.	2006 Feb 1	16325979
Inhibitory effect of caffeic acid phenethyl ester on the growth of C6 glioma cells in vitro and in vivo.	2006 Mar 28	15885897
A single dose of caffeic acid phenethyl ester prevents initiation in a medium-term rat hepatocarcinogenesis model.	2006 Nov 14	17106925
Bifunctional alkylating agent-induced p53 and nonclassical nuclear factor kappaB responses and cell death are altered by caffeic acid phenethyl ester: a potential role for antioxidant/electrophilic response-element signaling.	2007 Apr	17204746
Synthesis of trans-caffeate analogues and their bioactivities against HIV-1 integrase and cancer cell lines.	2008 Dec 15	18952420
Zinc deficiency induces vascular pro-inflammatory parameters associated with NF-kappaB and PPAR signaling.	2008 Oct	18845708
An approach to the study of gene expression in hepatocarcinogenesis initiation.	2010 Apr	20360939
Antitumor progression potential of caffeic acid phenethyl ester involving p75(NTR) in C6 glioma cells.	2010 Dec 5	20836997
Inhibitory effect of caffeic acid phenethyl ester on mice bearing tumor involving angiostatic and apoptotic activities.	2010 Jul 30	20433813
The PPARγ ligand rosiglitazone attenuates hypoxia-induced endothelin signaling in vitro and in vivo.	2011 Dec	21926265
A pharmacologically-based array to identify targets of cyclosporine A-induced toxicity in cultured renal proximal tubule cells.	2012 Jan 15	22155090
Inhibitory effects of caffeic acid phenethyl ester derivatives on replication of hepatitis C virus.	2013	24358168
Anticancer effects of thymoquinone, caffeic acid phenethyl ester and resveratrol on A549 non-small cell lung cancer cells exposed to benzo(a)pyrene.	2013	24289642
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
Suppression of nuclear factor erythroid 2-related factor 2 via extracellular signal-regulated kinase contributes to bleomycin-induced oxidative stress and fibrogenesis.	2013 Jun 20	23570914
Small molecule activators of the Nrf2-HO-1 antioxidant axis modulate heme metabolism and inflammation in BV2 microglia cells.	2013 Oct	23942037
Caffeic acid phenethyl ester inhibits diesel exhaust particle-induced inflammation of human middle ear epithelial cells via NOX4 inhibition.	2013 Sep	24224404
Caffeic acid phenethyl ester, a 5-lipoxygenase enzyme inhibitor, alleviates diabetic atherosclerotic manifestations: effect on vascular reactivity and stiffness.	2014 Apr 25	24508943
Cytotoxic and apoptotic effects of leptocarpin, a plant-derived sesquiterpene lactone, on human cancer cell lines.	2015 Dec 5	26562779
Transcriptional Regulation of the Sodium-activated Potassium Channel SLICK (KCNT2) Promoter by Nuclear Factor-κB.	2015 Jul 24	26100633

Substance Class	Chemical Created by `admin` on `Fri Dec 15 18:51:22 UTC 2023` Edited by `admin` on `Fri Dec 15 18:51:22 UTC 2023`
Record UNII	G960R9S5SK
Record Status	`Validated (UNII)`
Record Version

Download

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)