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]
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) 6
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 4
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
CHEMBL319244
CAS Number
115610-29-2
TTD ID
D06YGF
INTEDE ID
DR2154
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug
Drug Pharmacogenomic Perturbation (DPP)NEW Click to Jump to the Detailed DPP Information of This Drug
Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug

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]

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]

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]
CCAAT/enhancer-binding protein epsilon (CEBPE) OTKZA25M CEBPE_HUMAN Gene/Protein Processing [8]
Molecular Interaction Atlas (MIA) 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 Enhancement of caffeic acid phenethyl ester on all-trans retinoic acid-induced differentiation in human leukemia HL-60 cells. Toxicol Appl Pharmacol. 2006 Oct 1;216(1):80-8. doi: 10.1016/j.taap.2006.04.007.