Benzyl 3-(3,4-dihydroxy-5-nitrophenyl)acrylate

ID: ALA4447349

Chembl Id: CHEMBL4447349

PubChem CID: 155519072

Max Phase: Preclinical

Molecular Formula: C16H13NO6

Molecular Weight: 315.28

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(/C=C/c1cc(O)c(O)c([N+](=O)[O-])c1)OCc1ccccc1

Standard InChI:  InChI=1S/C16H13NO6/c18-14-9-12(8-13(16(14)20)17(21)22)6-7-15(19)23-10-11-4-2-1-3-5-11/h1-9,18,20H,10H2/b7-6+

Standard InChI Key:  PNWJBLQUWZHYLS-VOTSOKGWSA-N

Alternative Forms

1. Parent:

   

   ALA4447349

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 315.28

Molecular Weight (Monoisotopic): 315.0743

AlogP: 2.76

#Rotatable Bonds: 5

Polar Surface Area: 109.90

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 7.04

CX Basic pKa:

CX LogP: 3.57

CX LogD: 3.06

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.29

Np Likeness Score: -0.03

References

1. 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]

2. 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