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

ID: ALA3919207

PubChem CID: 134139857

Max Phase: Preclinical

Molecular Formula: C22H14N6

Molecular Weight: 362.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  c1ccc(-c2cc3c(cn2)ncc2ncn(-c4ccc5nc[nH]c5c4)c23)cc1

Standard InChI:  InChI=1S/C22H14N6/c1-2-4-14(5-3-1)18-9-16-20(10-23-18)24-11-21-22(16)28(13-27-21)15-6-7-17-19(8-15)26-12-25-17/h1-13H,(H,25,26)

Standard InChI Key:  KLCTWPGEFCWMHD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   11.6951  -16.3644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4003  -15.9556    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.1089  -16.3608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1096  -17.1798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8182  -17.5869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5264  -17.1761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5217  -16.3540    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.8126  -15.9506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4020  -17.5929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6926  -17.1808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0814  -17.7281    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.4131  -18.4786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2292  -18.3950    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.7731  -19.0012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5169  -19.7783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1154  -19.4379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5693  -18.8328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8697  -20.2211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0603  -20.3896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9704  -21.2114    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.7243  -21.5509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2800  -20.9388    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.2399  -17.5791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2427  -18.3983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9553  -18.8013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6620  -18.3848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6516  -17.5613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9385  -17.1621    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
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13  9  1  0
 14 15  2  0
 15 19  1  0
 18 16  1  0
 16 17  2  0
 17 14  1  0
 13 14  1  0
 18 19  2  0
 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:

   

   ALA3919207

   ---

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: 362.40

Molecular Weight (Monoisotopic): 362.1280

AlogP: 4.51

#Rotatable Bonds: 2

Polar Surface Area: 72.28

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.22

CX Basic pKa: 6.31

CX LogP: 3.40

CX LogD: 3.37

Aromatic Rings: 6

Heavy Atoms: 28

QED Weighted: 0.49

Np Likeness Score: -1.08

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