1-(1H-benzo[d]imidazol-6-yl)-8-(pyridin-4-yl)-1H-imidazo[4,5-c][1,7]naphthyridine

ID: ALA3966844

PubChem CID: 134150907

Max Phase: Preclinical

Molecular Formula: C21H13N7

Molecular Weight: 363.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  c1cc(-c2cc3c(cn2)ncc2ncn(-c4ccc5nc[nH]c5c4)c23)ccn1

Standard InChI:  InChI=1S/C21H13N7/c1-2-16-18(26-11-25-16)7-14(1)28-12-27-20-10-24-19-9-23-17(8-15(19)21(20)28)13-3-5-22-6-4-13/h1-12H,(H,25,26)

Standard InChI Key:  KBLDZBNLYGNNJS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    8.1368  -23.6405    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8455  -24.0457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8462  -24.8647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5547  -25.2718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2630  -24.8610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2583  -24.0389    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5492  -23.6355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1386  -25.2778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4292  -24.8657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8180  -25.4130    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1497  -26.1635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9658  -26.0799    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5097  -26.6861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2534  -27.4632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8520  -27.1228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3059  -26.5177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6063  -27.9060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7969  -28.0745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7070  -28.8963    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4609  -29.2358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0165  -28.6237    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.9764  -25.2640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9792  -26.0832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6918  -26.4862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3986  -26.0697    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.3882  -25.2462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6750  -24.8470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 10  2  0
  9  4  2  0
  3  2  2  0
  2  1  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  3  1  0
  9 10  1  0
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 11 12  2  0
 12 13  1  0
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 14 15  2  0
 15 19  1  0
 18 16  1  0
 16 17  2  0
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 13 14  1  0
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 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 18  1  0
  6 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3966844

   ---

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: 363.38

Molecular Weight (Monoisotopic): 363.1232

AlogP: 3.91

#Rotatable Bonds: 2

Polar Surface Area: 85.17

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.22

CX Basic pKa: 6.31

CX LogP: 2.18

CX LogD: 2.15

Aromatic Rings: 6

Heavy Atoms: 28

QED Weighted: 0.50

Np Likeness Score: -1.15

References

1. Glatthar R, Stojanovic A, Troxler T, Mattes H, Möbitz H, Beerli R, Blanz J, Gassmann E, Drückes P, Fendrich G, Gutmann S, Martiny-Baron G, Spence F, Hornfeld J, Peel JE, Sparrer H..  (2016)  Discovery of Imidazoquinolines as a Novel Class of Potent, Selective, and in Vivo Efficacious Cancer Osaka Thyroid (COT) Kinase Inhibitors.,  59  (16): [PMID:27502541] [10.1021/acs.jmedchem.6b00598]

Source

Source(1):

• Scientific Literature