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
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+
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Inhibitors of human immunodeficiency virus integrase. | 1993 Mar 15 |
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| Inhibition of HIV-1 integrase by flavones, caffeic acid phenethyl ester (CAPE) and related compounds. | 1994 Aug 3 |
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| Hydroxylated aromatic inhibitors of HIV-1 integrase. | 1995 Oct 13 |
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| HIV-1 integrase pharmacophore: discovery of inhibitors through three-dimensional database searching. | 1997 Mar 14 |
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| Plant phenolics decrease intestinal tumors in an animal model of familial adenomatous polyposis. | 2000 May |
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| Arylisothiocyanate-containing esters of caffeic acid designed as affinity ligands for HIV-1 integrase. | 2001 Jul |
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| Effects of caffeic acid phenethyl ester and alpha-tocopherol on reperfusion injury in rat brain. | 2003 Sep |
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| Protective effects of caffeic acid phenethyl ester on doxorubicin-induced cardiotoxicity in rats. | 2004 Jan-Feb |
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| Design and synthesis of novel dihydroxyindole-2-carboxylic acids as HIV-1 integrase inhibitors. | 2004 Mar |
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| IL-1beta regulates expression of Cx32, occludin, and claudin-2 of rat hepatocytes via distinct signal transduction pathways. | 2004 Oct 1 |
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| PAR1-mediated NFkappaB activation promotes survival of prostate cancer cells through a Bcl-xL-dependent mechanism. | 2005 Oct 15 |
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| 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 |
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| Protective effects of caffeic acid phenethyl ester, vitamin C, vitamin E and N-acetylcysteine on vancomycin-induced nephrotoxicity in rats. | 2007 May |
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| Synthesis of trans-caffeate analogues and their bioactivities against HIV-1 integrase and cancer cell lines. | 2008 Dec 15 |
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| Zinc deficiency induces vascular pro-inflammatory parameters associated with NF-kappaB and PPAR signaling. | 2008 Oct |
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| Effects of caffeic acid phenethyl ester on isoproterenol-induced myocardial infarction in rats. | 2010 Aug |
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| Antitumor progression potential of caffeic acid phenethyl ester involving p75(NTR) in C6 glioma cells. | 2010 Dec 5 |
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| Inhibitory effect of caffeic acid phenethyl ester on mice bearing tumor involving angiostatic and apoptotic activities. | 2010 Jul 30 |
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| 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 Jun 10 |
|
| Biochemical mechanism of caffeic acid phenylethyl ester (CAPE) selective toxicity towards melanoma cell lines. | 2010 Oct 6 |
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| Inhibitory effects of caffeic acid phenethyl ester derivatives on replication of hepatitis C virus. | 2013 |
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| Anticancer effects of thymoquinone, caffeic acid phenethyl ester and resveratrol on A549 non-small cell lung cancer cells exposed to benzo(a)pyrene. | 2013 |
|
| 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 |
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| 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 |
|
| Small molecule activators of the Nrf2-HO-1 antioxidant axis modulate heme metabolism and inflammation in BV2 microglia cells. | 2013 Oct |
|
| Caffeic acid phenethyl ester inhibits diesel exhaust particle-induced inflammation of human middle ear epithelial cells via NOX4 inhibition. | 2013 Sep |
|
| Caffeic acid phenethyl ester, a 5-lipoxygenase enzyme inhibitor, alleviates diabetic atherosclerotic manifestations: effect on vascular reactivity and stiffness. | 2014 Apr 25 |
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| Cytotoxic and apoptotic effects of leptocarpin, a plant-derived sesquiterpene lactone, on human cancer cell lines. | 2015 Dec 5 |
|
| Transcriptional Regulation of the Sodium-activated Potassium Channel SLICK (KCNT2) Promoter by Nuclear Factor-κB. | 2015 Jul 24 |
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Common Name | English | ||
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Official Name | English |
| Classification Tree | Code System | Code | ||
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DSLD |
3202 (Number of products:3)
Created by
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NCI_THESAURUS |
C2189
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DTXSID8040987
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104594-70-9
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8062
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C055494
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C63756
Created by
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Caffeic acid phenethyl ester
Created by
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G960R9S5SK
Created by
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5281787
Created by
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SUBSTANCE RECORD
