Details of the Drug

General Information of Drug (ID: DMRJKIV)

Drug Name

Caffeic acid phenethyl ester

Synonyms

Caffeic acid phenethyl ester; Phenethyl caffeate; 104594-70-9; CAPE; phenethyl 3-(3,4-dihydroxyphenyl)acrylate; Capeee; Phenylethyl caffeate; 115610-29-2; caffeic acid phenylethyl ester; UNII-G960R9S5SK; 2-phenylethyl caffeate; PHENETHYL CAFFEATE (CAPE); Caffeic acid-phenethyl ester; CHEBI:8062; G960R9S5SK; CHEMBL319244; 100981-80-4; Caffeic acid 2-phenylethyl ester; SWUARLUWKZWEBQ-VQHVLOKHSA-N; 2-phenylethyl 3-(3,4-dihydroxyphenyl)-2-propenoate; Caffeic Acid Phenethyl Ester, Synthetic; 2-Phenylethyl (2e)-3-(3,4-Dihydroxyphenyl

Indication

Disease Entry	ICD 11	Status	REF
Discovery agent	N.A.	Investigative	[1]
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Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

284.31

Logarithm of the Partition Coefficient (xlogp)

4.2

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

Chemical Identifiers

Formula: C17H16O4
IUPAC Name: 2-phenylethyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
Canonical SMILES: C1=CC=C(C=C1)CCOC(=O)/C=C/C2=CC(=C(C=C2)O)O
InChI: 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

Cross-matching ID

PubChem CID: 5281787
ChEBI ID: CHEBI:8062
CAS Number: 115610-29-2
TTD ID: D06YGF
INTEDE ID: DR2154

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Nuclear factor NF-kappa-B (NFKB)	TTSXVID	NFKB1_HUMAN ; NFKB2_HUMAN ; TF65_HUMAN ; RELB_HUMAN ; REL_HUMAN	Inhibitor	[1]

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Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Dextransucrase 4 (dsrF4)	DE1KTC4	GTF4_LEUME	Substrate	[2]
Dextransucrase 3 (dsrF3)	DED68N5	GTF3_LEUME	Substrate	[2]
Dextransucrase 2 (dsrF2)	DE174E0	GTF2_LEUME	Substrate	[2]
Dextransucrase 1 (dsrF1)	DEEPQJ8	GTF1_LEUME	Substrate	[2]
Amylosucrase (AMS)	DEEZYQV	Q1J0W0_DEIGD	Substrate	[3], [4]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Aldo-keto reductase family 1 member B1 (AKR1B1)	OTRX72TH	ALDR_HUMAN	Gene/Protein Processing	[5]
Aldo-keto reductase family 1 member B10 (AKR1B10)	OTOA4HTH	AK1BA_HUMAN	Gene/Protein Processing	[5]
Aldo-keto reductase family 1 member C1 (AKR1C1)	OTQKR4CM	AK1C1_HUMAN	Gene/Protein Processing	[5]
Aldo-keto reductase family 1 member C2 (AKR1C2)	OTQ2XMO3	AK1C2_HUMAN	Gene/Protein Processing	[5]
Aldo-keto reductase family 1 member C3 (AKR1C3)	OTU2SXBA	AK1C3_HUMAN	Gene/Protein Processing	[5]
Aldo-keto reductase family 1 member C4 (AKR1C4)	OTW2MMOF	AK1C4_HUMAN	Gene/Protein Processing	[5]
Baculoviral IAP repeat-containing protein 2 (BIRC2)	OTFXFREP	BIRC2_HUMAN	Gene/Protein Processing	[6]
Baculoviral IAP repeat-containing protein 3 (BIRC3)	OT3E95KB	BIRC3_HUMAN	Gene/Protein Processing	[6]
Breast cancer anti-estrogen resistance protein 1 (BCAR1)	OTKT2C2N	BCAR1_HUMAN	Post-Translational Modifications	[7]
Caspase-3 (CASP3)	OTIJRBE7	CASP3_HUMAN	Gene/Protein Processing	[8]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

References

1	Beneficial effects of caffeic acid phenethyl ester in a rat model of vascular injury. Br J Pharmacol. 2002 Jun;136(3):353-60.
2	Transglycosylation improved caffeic acid phenethyl ester anti-inflammatory activity and water solubility by Leuconostoc mesenteroides dextransucrase. J Agric Food Chem. 2019 Apr 24;67(16):4505-4512.
3	The complete genome and proteome of Laribacter hongkongensis reveal potential mechanisms for adaptations to different temperatures and habitats. PLoS Genet. 2009 Mar;5(3):e1000416.
4	Glycosylation enhances the physicochemical properties of caffeic acid phenethyl ester. J Microbiol Biotechnol. 2017 Nov 28;27(11):1916-1924.
5	Initro CAPE inhibitory activity towards human AKR1C3 and the molecular basis. Chem Biol Interact. 2016 Jun 25;253:60-5.
6	Caffeic acid phenethyl ester-induced PC-3 cell apoptosis is caspase-dependent and mediated through the loss of inhibitors of apoptosis proteins. BJU Int. 2004 Aug;94(3):402-6. doi: 10.1111/j.1464-410X.2004.04936.x.
7	Colon cancer chemopreventive drugs modulate integrin-mediated signaling pathways. Clin Cancer Res. 2000 Mar;6(3):949-56.
8	A caffeic acid phenethyl ester analog inhibits the proliferation of nasopharyngeal carcinoma cells via targeting epidermal growth factor receptor. J Biochem Mol Toxicol. 2020 Jul;34(7):e22491. doi: 10.1002/jbt.22491. Epub 2020 Mar 3.