Benzyl 2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)acrylate

ID: ALA4444830

Chembl Id: CHEMBL4444830

PubChem CID: 155517317

Max Phase: Preclinical

Molecular Formula: C17H12N2O6

Molecular Weight: 340.29

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C17H12N2O6/c18-9-13(17(22)25-10-11-4-2-1-3-5-11)6-12-7-14(19(23)24)16(21)15(20)8-12/h1-8,20-21H,10H2/b13-6+

Standard InChI Key:  RBBRZDXLYUXHJO-AWNIVKPZSA-N

Alternative Forms

1. Parent:

   

   ALA4444830

   ---

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: 340.29

Molecular Weight (Monoisotopic): 340.0695

AlogP: 2.66

#Rotatable Bonds: 5

Polar Surface Area: 133.69

Molecular Species: ACID

HBA: 7

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 6.07

CX Basic pKa:

CX LogP: 3.38

CX LogD: 2.12

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.21

Np Likeness Score: -0.53

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