N-(3-Chloro-4-fluorobenzyl)-1,4-dihydroxy-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxamide

ID: ALA3125970

Chembl Id: CHEMBL3125970

PubChem CID: 76321849

Max Phase: Preclinical

Molecular Formula: C16H11ClFN3O4

Molecular Weight: 363.73

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(NCc1ccc(F)c(Cl)c1)c1c(O)c2cccnc2n(O)c1=O

Standard InChI:  InChI=1S/C16H11ClFN3O4/c17-10-6-8(3-4-11(10)18)7-20-15(23)12-13(22)9-2-1-5-19-14(9)21(25)16(12)24/h1-6,22,25H,7H2,(H,20,23)

Standard InChI Key:  ZMWNOXHZOQBNOQ-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA3125970

   N-[(3-chloro-4-fluoro-phenyl)methyl]-1,4-dihydroxy-2-oxo-1,8-naphthyridine-3-carboxamide

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: 363.73

Molecular Weight (Monoisotopic): 363.0422

AlogP: 2.06

#Rotatable Bonds: 3

Polar Surface Area: 104.45

Molecular Species: ACID

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.12

CX Basic pKa: 0.43

CX LogP: 1.33

CX LogD: -1.48

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.62

Np Likeness Score: -1.43

References

1. Zhao XZ, Smith SJ, Métifiot M, Johnson BC, Marchand C, Pommier Y, Hughes SH, Burke TR..  (2014)  Bicyclic 1-hydroxy-2-oxo-1,2-dihydropyridine-3-carboxamide-containing HIV-1 integrase inhibitors having high antiviral potency against cells harboring raltegravir-resistant integrase mutants.,  57  (4): [PMID:24471816] [10.1021/jm401902n]

2. Wang Y, Gu SX, He Q, Fan R..  (2021)  Advances in the development of HIV integrase strand transfer inhibitors.,  225  [PMID:34425310] [10.1016/j.ejmech.2021.113787]

Source

Source(1):

• Scientific Literature