US9062043, Table 20b, Compound 28

ID: ALA3703937

PubChem CID: 58485097

Max Phase: Preclinical

Molecular Formula: C19H13ClN4O2

Molecular Weight: 364.79

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1cc2c(Nc3cccc(Cl)c3)nc3cc(C(=O)O)ccc3c2cn1

Standard InChI:  InChI=1S/C19H13ClN4O2/c20-11-2-1-3-12(7-11)23-18-14-8-17(21)22-9-15(14)13-5-4-10(19(25)26)6-16(13)24-18/h1-9H,(H2,21,22)(H,23,24)(H,25,26)

Standard InChI Key:  PCNHIHDEJGRLDW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
    2.3383   -1.3500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2982    3.7531    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2960    5.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5925    6.0085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5873    7.5085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2856    8.2540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0108    7.4995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0521    8.0959    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.0056    5.9995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2991    3.7500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5981    3.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8971    3.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1962    3.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1962    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8971    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5981    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4975    3.7477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5359    3.1462    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4996    4.9477    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13  7  1  0
  5 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 15  1  0
 20 21  2  0
 21  4  1  0
 21 22  1  0
 22 23  2  0
 23  2  1  0
 17 24  1  0
 24 25  2  0
 24 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3703937

   3-Amino-5-(3-chloroanilino)benzo[c][2,6]naphthyridine-8-carboxylic acid

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: 364.79

Molecular Weight (Monoisotopic): 364.0727

AlogP: 4.46

#Rotatable Bonds: 3

Polar Surface Area: 101.13

Molecular Species: ACID

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.21

CX Basic pKa: 7.17

CX LogP: 2.25

CX LogD: 1.83

Aromatic Rings: 4

Heavy Atoms: 26

QED Weighted: 0.46

Np Likeness Score: -0.80

References

1.  (2015)  Fused tricyclic compounds as serine-threonine protein kinase and PARP modulators, 

Source

Source(1):

• BindingDB Database