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
Effects of caffeic acid phenethyl ester and alpha-tocopherol on reperfusion injury in rat brain.	2003 Sep	12910483
Caffeic acid phenethyl ester prevents neonatal hypoxic-ischaemic brain injury.	2004 Dec	15469948
Protective effects of caffeic acid phenethyl ester on doxorubicin-induced cardiotoxicity in rats.	2004 Jan-Feb	14745846
Design and synthesis of novel dihydroxyindole-2-carboxylic acids as HIV-1 integrase inhibitors.	2004 Mar	15185725
Inhibition of multidrug resistance proteins MRP1 and MRP2 by a series of alpha,beta-unsaturated carbonyl compounds.	2005 Jun 15	15885658
Caffeic acid phenethyl ester (CAPE) prevents transformation of human cells by arsenite (As) and suppresses growth of As-transformed cells.	2005 Sep 15	16085347
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
A single dose of caffeic acid phenethyl ester prevents initiation in a medium-term rat hepatocarcinogenesis model.	2006 Nov 14	17106925
Protective effects of caffeic acid phenethyl ester, vitamin C, vitamin E and N-acetylcysteine on vancomycin-induced nephrotoxicity in rats.	2007 May	17448119
Synthesis of trans-caffeate analogues and their bioactivities against HIV-1 integrase and cancer cell lines.	2008 Dec 15	18952420
Involvement of epigenetic mechanisms in the regulation of secreted phospholipase A2 expressions in Jurkat leukemia cells.	2008 Nov	18953428
Effects of caffeic acid phenethyl ester on isoproterenol-induced myocardial infarction in rats.	2010 Aug	20693123
p52-Bcl3 complex promotes cyclin D1 expression in BEAS-2B cells in response to low concentration arsenite.	2010 Jun 29	20420878
Biochemical mechanism of caffeic acid phenylethyl ester (CAPE) selective toxicity towards melanoma cell lines.	2010 Oct 6	20685355
The metabolic bioactivation of caffeic acid phenethyl ester (CAPE) mediated by tyrosinase selectively inhibits glutathione S-transferase.	2011 Jul 15	21458432
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
Cytotoxic and apoptotic effects of leptocarpin, a plant-derived sesquiterpene lactone, on human cancer cell lines.	2015 Dec 5	26562779

Substance Class	Chemical Created by `admin` on `Fri Dec 15 18:51:22 GMT 2023` Edited by `admin` on `Fri Dec 15 18:51:22 GMT 2023`
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 [INCI]

Common Name

English

PHENETHYL CAFFEATE

Official Name

English

Classification Tree Code System Code

DSLD

3202 (Number of products:3)