8-(3-Nitro-phenyl)-6-phenyl-[1,7]naphthyridine

ID: ALA161465

PubChem CID: 10711281

Max Phase: Preclinical

Molecular Formula: C20H13N3O2

Molecular Weight: 327.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=[N+]([O-])c1cccc(-c2nc(-c3ccccc3)cc3cccnc23)c1

Standard InChI:  InChI=1S/C20H13N3O2/c24-23(25)17-10-4-8-15(12-17)20-19-16(9-5-11-21-19)13-18(22-20)14-6-2-1-3-7-14/h1-13H

Standard InChI Key:  SRVUGPYWYLBZNI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
    2.5417    0.2583    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0750   -1.8375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0292   -0.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5417    0.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5042    0.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0292   -0.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5542   -1.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5000    0.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0167    1.1583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5542   -0.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0667   -2.4292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9875   -0.0500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7417   -1.7167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0542    1.1708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5125   -0.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0417   -1.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5167   -1.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9875    1.1583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4667    0.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5792    0.8708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0500    1.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4667    0.8583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5625    2.0708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0917    1.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0875    1.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  7  1  0
  3  1  1  0
  4  1  2  0
  5  3  2  0
  6  3  1  0
  7 10  2  0
  8  9  2  0
  9  4  1  0
 10  6  1  0
 11  2  1  0
 12  5  1  0
 13  2  2  0
 14  4  1  0
 15  6  2  0
 16 17  2  0
 17 15  1  0
 18  8  1  0
 19 12  2  0
 20 14  2  0
 21 14  1  0
 22 18  2  0
 23 21  2  0
 24 20  1  0
 25 23  1  0
  8  5  1  0
 24 25  2  0
 19 22  1  0
  7 16  1  0
M  CHG  2   2   1  11  -1
M  END

Alternative Forms

1. Parent:

   

   ALA161465

   6-Phenyl-8-(3-nitrophenyl)-1,7-naphthyridine

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: 327.34

Molecular Weight (Monoisotopic): 327.1008

AlogP: 4.87

#Rotatable Bonds: 3

Polar Surface Area: 68.92

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 1.73

CX LogP: 4.92

CX LogD: 4.92

Aromatic Rings: 4

Heavy Atoms: 25

QED Weighted: 0.40

Np Likeness Score: -1.22

References

1. Hersperger R, Bray-French K, Mazzoni L, Müller T..  (2000)  Palladium-catalyzed cross-coupling reactions for the synthesis of 6, 8-disubstituted 1,7-naphthyridines: a novel class of potent and selective phosphodiesterase type 4D inhibitors.,  43  (4): [PMID:10691693] [10.1021/jm991094u]

Source

Source(1):

• Scientific Literature