5-(naphthalen-2-ylamino)benzo[c][2,6]naphthyridine-8-carboxylic acid

ID: ALA5287614

Max Phase: Preclinical

Molecular Formula: C23H15N3O2

Molecular Weight: 365.39

Names and Identifiers

Canonical SMILES:  O=C(O)c1ccc2c(c1)nc(Nc1ccc3ccccc3c1)c1ccncc12

Standard InChI:  InChI=1S/C23H15N3O2/c27-23(28)16-6-8-18-20-13-24-10-9-19(20)22(26-21(18)12-16)25-17-7-5-14-3-1-2-4-15(14)11-17/h1-13H,(H,25,26)(H,27,28)

Standard InChI Key:  RDMBYNWOAJKXAP-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 28 32  0  0  0  0  0  0  0  0999 V2000
    3.2051   -0.2642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4832   -0.6637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4630   -1.4876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1712   -1.9106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8936   -1.5120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9105   -0.6856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7769   -0.2418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7929    0.5835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5148    0.9831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2225    0.5603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0886    1.0042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3721    0.6107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3380    1.0350    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0645    0.6356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0859   -0.1968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3729   -0.6228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3535   -0.2202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0645   -0.6450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0491   -1.4756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3249   -1.8742    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3875   -1.4486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8002   -0.5894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5099   -0.1654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4899    0.6648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7688    1.0563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1942    1.0855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9105    0.6958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1733    1.9106    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  4  3  2  0
  5  4  1  0
  1  6  1  0
  6  5  2  0
  2  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  1 10  1  0
  8 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 16 15  1  0
 16 17  2  0
 17 12  1  0
 17 18  1  0
 19 18  2  0
 20 19  1  0
 16 21  1  0
 21 20  2  0
 22 15  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 14  1  0
 24 26  1  0
 26 27  2  0
 26 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5287614

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 365.39

Molecular Weight (Monoisotopic): 365.1164

AlogP: 5.38

#Rotatable Bonds: 3

Polar Surface Area: 75.11

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.02

CX Basic pKa: 4.61

CX LogP: 3.68

CX LogD: 1.32

Aromatic Rings: 5

Heavy Atoms: 28

QED Weighted: 0.42

Np Likeness Score: -0.84

References

1. Davis-Gilbert ZW, Krämer A, Dunford JE, Howell S, Senbabaoglu F, Wells CI, Bashore FM, Havener TM, Smith JL, Hossain MA, Oppermann U, Drewry DH, Axtman AD..  (2023)  Discovery of a Potent and Selective Naphthyridine-Based Chemical Probe for Casein Kinase 2.,  14  (4): [PMID:37077385] [10.1021/acsmedchemlett.2c00530]

Source

Source(1):

• Scientific Literature