5-(naphthalen-2-ylamino)pyrimido[4,5-c]quinoline-8-carboxylic acid

ID: ALA5288335

Max Phase: Preclinical

Molecular Formula: C22H14N4O2

Molecular Weight: 366.38

Names and Identifiers

Canonical SMILES:  O=C(O)c1ccc2c(c1)nc(Nc1ccc3ccccc3c1)c1ncncc12

Standard InChI:  InChI=1S/C22H14N4O2/c27-22(28)15-6-8-17-18-11-23-12-24-20(18)21(26-19(17)10-15)25-16-7-5-13-3-1-2-4-14(13)9-16/h1-12H,(H,25,26)(H,27,28)

Standard InChI Key:  QVDFUUYVVOAFGS-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   -1.3532    1.6460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6218    2.0273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5846    2.8448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2793    3.2905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0071    2.9111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3880    0.8272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1210    0.4451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8161    0.8895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7757    1.7113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1590   -0.3742    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4684   -0.8168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7348   -0.4344    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0366   -0.8865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0746   -1.7161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8111   -2.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5087   -1.6454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2361   -2.0245    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2806   -2.8438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5870   -3.2905    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8540   -2.9084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6209   -2.1614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3567   -1.7778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3969   -0.9522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6977   -0.5037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1242   -0.5730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1640    0.2436    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8161   -1.0187    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
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  6  5  2  0
  2  7  1  0
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  9 10  2  0
  1 10  1  0
  8 11  1  0
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 12 17  1  0
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 20 21  1  0
 21 16  2  0
 15 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 14 25  1  0
 24 26  1  0
 26 27  2  0
 26 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5288335

   ---

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: 366.38

Molecular Weight (Monoisotopic): 366.1117

AlogP: 4.77

#Rotatable Bonds: 3

Polar Surface Area: 88.00

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.62

CX Basic pKa: 1.18

CX LogP: 4.26

CX LogD: 0.93

Aromatic Rings: 5

Heavy Atoms: 28

QED Weighted: 0.45

Np Likeness Score: -0.91

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