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=CC=C(\C=C\C(=O)OCCC2=CC=CC=C2)C=C1O

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 8504	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 8504	1.7 µM [IC50]
Human immunodeficiency virus type 1 integrase 20 Target ID: CHEMBL3471 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7473544	Inhibitor 8504	7.0 µM [IC50]
Arachidonate 5-lipoxygenase 52 Target ID: CHEMBL215 Sources: https://www.ncbi.nlm.nih.gov/pubmed/29953727	Inhibitor 8504	1.01 µM [IC50]
Apoptosis 156 Target ID: map04210 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28926932	Activator 1447	27.84 µM [IC50]

PubMed

Title	Date	PubMed
Cytotoxic and apoptotic effects of leptocarpin, a plant-derived sesquiterpene lactone, on human cancer cell lines.	2015-12-05	26562779
Transcriptional Regulation of the Sodium-activated Potassium Channel SLICK (KCNT2) Promoter by Nuclear Factor-κB.	2015-07-24	26100633
Caffeic acid phenethyl ester, a 5-lipoxygenase enzyme inhibitor, alleviates diabetic atherosclerotic manifestations: effect on vascular reactivity and stiffness.	2014-04-25	24508943
Arsenic augments the uptake of oxidized LDL by upregulating the expression of lectin-like oxidized LDL receptor in mouse aortic endothelial cells.	2013-12-15	24145059
Small molecule activators of the Nrf2-HO-1 antioxidant axis modulate heme metabolism and inflammation in BV2 microglia cells.	2013-10	23942037
Caffeic acid phenethyl ester inhibits diesel exhaust particle-induced inflammation of human middle ear epithelial cells via NOX4 inhibition.	2013-09	24224404
Suppression of nuclear factor erythroid 2-related factor 2 via extracellular signal-regulated kinase contributes to bleomycin-induced oxidative stress and fibrogenesis.	2013-06-20	23570914
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
Cancer prevention mediated by caffeic acid phenethyl ester involves cyp2b1/2 modulation in hepatocarcinogenesis.	2012-04	22291063
A pharmacologically-based array to identify targets of cyclosporine A-induced toxicity in cultured renal proximal tubule cells.	2012-01-15	22155090
The PPARγ ligand rosiglitazone attenuates hypoxia-induced endothelin signaling in vitro and in vivo.	2011-12	21926265
The metabolic bioactivation of caffeic acid phenethyl ester (CAPE) mediated by tyrosinase selectively inhibits glutathione S-transferase.	2011-07-15	21458432
Cytotoxicity of arsenic trioxide is enhanced by (-)-epigallocatechin-3-gallate via suppression of ferritin in cancer cells.	2011-01-01	20950636
Caffeic acid phenethyl ester suppresses the production of adipocytokines, leptin, tumor necrosis factor -alpha and resistin, during differentiation to adipocytes in 3T3-L1 cells.	2011	21467634
Antitumor progression potential of caffeic acid phenethyl ester involving p75(NTR) in C6 glioma cells.	2010-12-05	20836997
Biochemical mechanism of caffeic acid phenylethyl ester (CAPE) selective toxicity towards melanoma cell lines.	2010-10-06	20685355
Effects of caffeic acid phenethyl ester on isoproterenol-induced myocardial infarction in rats.	2010-08	20693123
Inhibitory effect of caffeic acid phenethyl ester on mice bearing tumor involving angiostatic and apoptotic activities.	2010-07-30	20433813
p52-Bcl3 complex promotes cyclin D1 expression in BEAS-2B cells in response to low concentration arsenite.	2010-06-29	20420878
Structure-activity relationships in the cytoprotective effect of caffeic acid phenethyl ester (CAPE) and fluorinated derivatives: effects on heme oxygenase-1 induction and antioxidant activities.	2010-06-10	20226179
An approach to the study of gene expression in hepatocarcinogenesis initiation.	2010-04	20360939
Effects of caffeic acid phenethyl ester on endotoxin-induced cardiac stress in rats: a possible mechanism of protection.	2009-10-01	21472898
Synthesis of trans-caffeate analogues and their bioactivities against HIV-1 integrase and cancer cell lines.	2008-12-15	18952420
Involvement of epigenetic mechanisms in the regulation of secreted phospholipase A2 expressions in Jurkat leukemia cells.	2008-11	18953428
Zinc deficiency induces vascular pro-inflammatory parameters associated with NF-kappaB and PPAR signaling.	2008-10	18845708
Evidence that the anticarcinogenic effect of caffeic acid phenethyl ester in the resistant hepatocyte model involves modifications of cytochrome P450.	2008-07	18397917
Protective effect of caffeic acid phenethyl ester against carbon tetrachloride-induced hepatotoxicity in mice.	2008-06-03	18436364
Protective effects of caffeic acid phenethyl ester, vitamin C, vitamin E and N-acetylcysteine on vancomycin-induced nephrotoxicity in rats.	2007-05	17448119
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.	2007-04	17204746
A single dose of caffeic acid phenethyl ester prevents initiation in a medium-term rat hepatocarcinogenesis model.	2006-11-14	17106925
Enhancement of caffeic acid phenethyl ester on all-trans retinoic acid-induced differentiation in human leukemia HL-60 cells.	2006-10-01	16766008
Inhibitory effect of caffeic acid phenethyl ester on the growth of C6 glioma cells in vitro and in vivo.	2006-03-28	15885897
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.	2006-02-01	16325979
The novel cytokine p43 induces IL-12 production in macrophages via NF-kappaB activation, leading to enhanced IFN-gamma production in CD4+ T cells.	2006-01-01	16365417
Arsenite enhances tumor necrosis factor-alpha-induced expression of vascular cell adhesion molecule-1.	2005-11-15	16271621
PAR1-mediated NFkappaB activation promotes survival of prostate cancer cells through a Bcl-xL-dependent mechanism.	2005-10-15	16052512
Caffeic acid phenethyl ester (CAPE) prevents transformation of human cells by arsenite (As) and suppresses growth of As-transformed cells.	2005-09-15	16085347
Inhibition of multidrug resistance proteins MRP1 and MRP2 by a series of alpha,beta-unsaturated carbonyl compounds.	2005-06-15	15885658
Anti-HIV activities of natural antioxidant caffeic acid derivatives: toward an antiviral supplementation diet.	2005	16029149
Caffeic acid phenethyl ester prevents neonatal hypoxic-ischaemic brain injury.	2004-12	15469948
IL-1beta regulates expression of Cx32, occludin, and claudin-2 of rat hepatocytes via distinct signal transduction pathways.	2004-10-01	15350541
Caffeic acid phenethyl ester as a protective agent against doxorubicin nephrotoxicity in rats.	2004-10	15369732
Caffeic acid phenethyl ester-induced PC-3 cell apoptosis is caspase-dependent and mediated through the loss of inhibitors of apoptosis proteins.	2004-08	15291876
Design and synthesis of novel dihydroxyindole-2-carboxylic acids as HIV-1 integrase inhibitors.	2004-03	15185725
Protective effects of caffeic acid phenethyl ester on doxorubicin-induced cardiotoxicity in rats.	2004-01-28	14745846
HIV-1 integrase pharmacophore: discovery of inhibitors through three-dimensional database searching.	1997-03-14	9083480
Hydroxylated aromatic inhibitors of HIV-1 integrase.	1995-10-13	7473544
Inhibition of HIV-1 integrase by flavones, caffeic acid phenethyl ester (CAPE) and related compounds.	1994-08-03	7520698
Inhibitors of human immunodeficiency virus integrase.	1993-03-15	8460151

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:22:46 GMT 2025` Edited by `admin` on `Mon Mar 31 19:22:46 GMT 2025`
Record UNII	G960R9S5SK
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CAFFEIC ACID PHENETHYL ESTER

Common Name

English

PHENETHYL CAFFEATE

Preferred Name

English

Classification Tree Code System Code

DSLD

3202 (Number of products:3)