Drug Details

General Information of the Drug (ID: DR5742)
Name
Caffeic acid phenethyl ester
Synonyms
Caffeic acid phenethyl ester; Phenethyl caffeate; 104594-70-9; CAPE; Phenylethyl caffeate; phenethyl 3-(3,4-dihydroxyphenyl)acrylate; Capeee; 115610-29-2; caffeic acid phenylethyl ester; PHENETHYL CAFFEATE (CAPE); UNII-G960R9S5SK; 2-phenylethyl caffeate; 2-phenylethyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate; CHEBI:8062; CHEMBL319244; G960R9S5SK; (E)-phenethyl 3-(3,4-dihydroxyphenyl)acrylate; MFCD00866470; 100981-80-4; 2-Phenylethyl (2e)-3-(3,4-Dihydroxyphenyl)prop-2-Enoate; 2-phenylethyl (2E)-3-(3,4-dihydroxyphenyl)acrylate; 2-Propenoic acid, 3-(3,4-dihydroxyphenyl)-, 2-phenylethyl ester; SMR000326751; SR-01000075785; 2-phenylethyl 3-(3,4-dihydroxyphenyl)prop-2-enoate; caffeic-acid-phenethyl-ester; phenethyl 3,4-dihydroxycinnamate; 3-(3,4-Dihydroxyphenyl)-2-propenoic acid 2-phenylethyl ester; QAP; 2-phenylethyl 3-(3,4-dihydroxyphenyl)-2-propenoate; Caffeic Acid Phenethyl Ester, Synthetic; Phenethyl (E)-caffeate; caffeic acidphenethylester; caffeic acid phenethylester; caffeic acid phenylethylester; Lopac0_000269; BSPBio_001560; BSPBio_003586; MLS000859889; MLS002207297; SPECTRUM1502209; phenethyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate; ZINC1083; CHEBI:93478; DTXSID80861176; FR102; HMS1361N22; HMS1791N22; HMS1989N22; HMS2233J04; HMS3260F20; HMS3402N22; HMS3413D22; HMS3649C16; HMS3677D22; Phenylethyl 3,4-dihydroxycinnamate; Caffeic acid beta-phenylethyl ester; Trans-Caffeic Acid Phenethyl Ester; BCP27877; Caffeic acid phenethyl ester(CAPE); EBD26363; HY-N0274; Tox21_500269; BDBM50029207; Caffeic acid phenethyl ester (CAPE); CCG-39542; s7414; 2-Propenoic acid, 3-(3,4-dihydroxyphenyl)-, 2-phenylethyl ester, (E)-; AKOS015888207; AC-8896; LP00269; SDCCGSBI-0050257.P002; IDI1_034030; QTL1_000016; NCGC00093727-01; NCGC00093727-02; NCGC00093727-03; NCGC00093727-04; NCGC00093727-05; NCGC00093727-06; NCGC00093727-07; NCGC00093727-08; NCGC00093727-09; NCGC00093727-16; NCGC00260954-01; AS-14021; I793; LS-14562; CS-0008774; EU-0100269; SW219156-1; B-6327; C 8221; C10484; 3,4-Dihydroxy-trans-cinnamic acid phenethyl ester; SR-01000075785-1; SR-01000075785-6; SR-01000075785-9; BRD-K84709232-001-02-6; BRD-K96188950-001-02-9; BRD-K96188950-001-04-5; Caffeic acid phenethyl ester, >=97% (HPLC), powder; Q15410860; 3-(3,4-Dihydroxy-phenyl)-acrylic acid phenethyl ester; Methanone, 1,1'-(1,2-cyclopropanediyl)bis[1-phenyl-; (E)-3-(3,4-Dihydroxy-phenyl)-acrylic acid phenethyl ester
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Molecular Type
Small molecule
Disease Ovarian cancer [ICD-11: 2C73] Investigative [1]
Structure
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2D MOL

3D MOL

    Click to Show/Hide the Molecular Information and External Link(s) of This Natural Product
Formula
C17H16O4
PubChem CID
5281787
Canonical SMILES
C1=CC=C(C=C1)CCOC(=O)C=CC2=CC(=C(C=C2)O)O
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+
InChIKey
SWUARLUWKZWEBQ-VQHVLOKHSA-N
CAS Number
CAS 115610-29-2
ChEBI ID
CHEBI:8062
TTD Drug ID
D06YGF
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Natural Product(s) Able to Enhance the Efficacy of This Drug
          Withaferin A      Withania somnifera     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Down-regulation Expression TP53  Molecule Info 
Pathway MAP
                    In-vitro Model SK-OV-3 CVCL_0532 Ovarian serous cystadenocarcinoma Homo sapiens
OVK18 CVCL_3770 Ovarian endometrioid adenocarcinoma Homo sapiens
HeLa CVCL_0030 Endocervical adenocarcinoma Homo sapiens
SKG-II CVCL_2794 Cervical squamous cell carcinoma Homo sapiens
SKG-IIIb CVCL_2795 Cervical squamous cell carcinoma Homo sapiens
ME-180 CVCL_1401 Cervical squamous cell carcinoma Homo sapiens
                    In-vivo Model Effect of Wi-A, CAPE and their combination was examined by female 4-5 weeks old BALB/c nude mice in vivo tumor growth assay using subcutaneous xenografts of SKOV-3.
                    Experimental
                    Result(s)		 A combination of Wi-A and CAPE offers selective toxicity and better potency to cancer cells.
Target and Pathway
Target(s) Nuclear factor NF-kappa-B (NFKB)  Molecule Info  [3]
KEGG Pathway MAPK signaling pathway Click to Show/Hide
2 NF-kappa B signaling pathway
3 Osteoclast differentiation
4 Legionellosis
5 HTLV-I infection
6 Epstein-Barr virus infection
7 Pathways in cancer
8 Viral carcinogenesis
NetPath Pathway IL5 Signaling Pathway Click to Show/Hide
Panther Pathway Apoptosis signaling pathway Click to Show/Hide
2 B cell activation
3 Inflammation mediated by chemokine and cytokine signaling pathway
4 T cell activation
5 Toll receptor signaling pathway
Pathwhiz Pathway Intracellular Signalling Through Adenosine Receptor A2a and Adenosine Click to Show/Hide
2 Intracellular Signalling Through Adenosine Receptor A2b and Adenosine
Pathway Interaction Database IL12-mediated signaling events Click to Show/Hide
2 Alternative NF-kappaB pathway
Reactome RIP-mediated NFkB activation via ZBP1 Click to Show/Hide
2 DEx/H-box helicases activate type I IFN and inflammatory cytokines production
3 TAK1 activates NFkB by phosphorylation and activation of IKKs complex
4 Interleukin-1 processing
5 IKBKG deficiency causes anhidrotic ectodermal dysplasia with immunodeficiency (EDA-ID) (via TLR)
6 IkBA variant leads to EDA-ID
7 Dectin-1 mediated noncanonical NF-kB signaling
8 NIK-->noncanonical NF-kB signaling
9 TRAF6 mediated NF-kB activation
WikiPathways Toll-like receptor signaling pathway Click to Show/Hide
2 DNA Damage Response (only ATM dependent)
3 SIDS Susceptibility Pathways
4 Nuclear Receptors Meta-Pathway
5 Cytosolic sensors of pathogen-associated DNA
6 TAK1 activates NFkB by phosphorylation and activation of IKKs complex
7 EBV LMP1 signaling
8 TNF alpha Signaling Pathway
9 TSLP Signaling Pathway
10 Neural Crest Differentiation
11 TWEAK Signaling Pathway
12 RANKL/RANK Signaling Pathway
13 RIG-I/MDA5 mediated induction of IFN-alpha/beta pathways
14 Interleukin-1 processing
15 Folate Metabolism
16 Vitamin B12 Metabolism
17 Selenium Micronutrient Network
18 Regulation of toll-like receptor signaling pathway
References
Reference 1 Caffeic Acid Phenethyl Ester (CAPE) Induced Apoptosis in Serous Ovarian Cancer OV7 Cells by Deregulation of BCL2/BAX Genes. Molecules. 2020 Jul 31;25(15):3514.
Reference 2 Combination of Withaferin-A and CAPE Provides Superior Anticancer Potency: Bioinformatics and Experimental Evidence to Their Molecular Targets and Mechanism of Action. Cancers (Basel). 2020 May 5;12(5):1160.
Reference 3 Beneficial effects of caffeic acid phenethyl ester in a rat model of vascular injury. Br J Pharmacol. 2002 Jun;136(3):353-60.
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