(E)-phenethyl 3-(3,4-dihydroxy-5-nitrophenyl)acrylate

ID: ALA481644

Chembl Id: CHEMBL481644

PubChem CID: 44571553

Max Phase: Preclinical

Molecular Formula: C17H15NO6

Molecular Weight: 329.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(/C=C/c1cc(O)c(O)c([N+](=O)[O-])c1)OCCc1ccccc1

Standard InChI:  InChI=1S/C17H15NO6/c19-15-11-13(10-14(17(15)21)18(22)23)6-7-16(20)24-9-8-12-4-2-1-3-5-12/h1-7,10-11,19,21H,8-9H2/b7-6+

Standard InChI Key:  WIKOXWOZNIRBTH-VOTSOKGWSA-N

Alternative Forms

1. Parent:

   

   ALA481644

   2-Phenylethyl 3-(3,4-dihydroxy-5-nitrophenyl)prop-2-enoate

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 329.31

Molecular Weight (Monoisotopic): 329.0899

AlogP: 2.81

#Rotatable Bonds: 6

Polar Surface Area: 109.90

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.04

CX Basic pKa: ┄

CX LogP: 3.86

CX LogD: 3.35

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.28

Np Likeness Score: 0.06

References

1. Xia CN, Li HB, Liu F, Hu WX..  (2008)  Synthesis of trans-caffeate analogues and their bioactivities against HIV-1 integrase and cancer cell lines.,  18  (24): [PMID:18952420] [10.1016/j.bmcl.2008.10.046]

2. Chen HZ, Chen YB, Lv YP, Zeng F, Zhang J, Zhou YL, Li HB, Chen LF, Zhou BJ, Gao JR, Xia CN..  (2014)  Synthesis and antitumor activity of feruloyl and caffeoyl derivatives.,  24  (18): [PMID:25160837] [10.1016/j.bmcl.2014.08.024]

3. Silva T, Mohamed T, Shakeri A, Rao PPN, Soares da Silva P, Remião F, Borges F..  (2019)  Repurposing nitrocatechols: 5-Nitro-α-cyanocarboxamide derivatives of caffeic acid and caffeic acid phenethyl ester effectively inhibit aggregation of tau-derived hexapeptide AcPHF6.,  167  [PMID:30771602] [10.1016/j.ejmech.2019.02.006]

4. Silva T, Mohamed T, Shakeri A, Rao PP, Martínez-González L, Pérez DI, Martínez A, Valente MJ, Garrido J, Uriarte E, Serrão P, Soares-da-Silva P, Remião F, Borges F..  (2016)  Development of Blood-Brain Barrier Permeable Nitrocatechol-Based Catechol O-Methyltransferase Inhibitors with Reduced Potential for Hepatotoxicity.,  59  (16): [PMID:27463695] [10.1021/acs.jmedchem.6b00666]

Source

Source(1):

• Scientific Literature