1-(1H-benzo[d]imidazol-6-yl)-8-(thiophen-3-yl)-1H-imidazo[4,5-c][1,7]naphthyridine

ID: ALA3980906

PubChem CID: 134156928

Max Phase: Preclinical

Molecular Formula: C20H12N6S

Molecular Weight: 368.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  c1nc2ccc(-n3cnc4cnc5cnc(-c6ccsc6)cc5c43)cc2[nH]1

Standard InChI:  InChI=1S/C20H12N6S/c1-2-15-17(24-10-23-15)5-13(1)26-11-25-19-8-22-18-7-21-16(6-14(18)20(19)26)12-3-4-27-9-12/h1-11H,(H,23,24)

Standard InChI Key:  VVXFXVFJMAGVLA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 32  0  0  0  0  0  0  0  0999 V2000
    1.2945   -9.7774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9996   -9.3685    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7083   -9.7738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7090  -10.5928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4176  -10.9998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1258  -10.5890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1211   -9.7669    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4120   -9.3635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0014  -11.0059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2920  -10.5937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6808  -11.1411    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0125  -11.8916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8286  -11.8079    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3725  -12.4141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1162  -13.1913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7148  -12.8508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1687  -12.2457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8352  -10.9970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9238  -11.8094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7238  -11.9762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1297  -11.2668    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.5805  -10.6618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4614  -13.6322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6597  -13.8025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5740  -14.6176    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3227  -14.9511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8711  -14.3420    0.0000 N   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 24  1  0
 23 16  1  0
 16 17  2  0
 17 14  1  0
 13 14  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 18  2  0
  6 18  1  0
 23 24  2  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 27 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3980906

   ---

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: 368.43

Molecular Weight (Monoisotopic): 368.0844

AlogP: 4.57

#Rotatable Bonds: 2

Polar Surface Area: 72.28

Molecular Species: NEUTRAL

HBA: 6

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: 3.18

CX LogD: 3.15

Aromatic Rings: 6

Heavy Atoms: 27

QED Weighted: 0.49

Np Likeness Score: -1.65

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