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

ID: ALA3910848

PubChem CID: 134132267

Max Phase: Preclinical

Molecular Formula: C22H13N5S

Molecular Weight: 379.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  c1cnc2ccc(-n3cnc4cnc5cnc(-c6ccsc6)cc5c43)cc2c1

Standard InChI:  InChI=1S/C22H13N5S/c1-2-14-8-16(3-4-18(14)23-6-1)27-13-26-21-11-25-20-10-24-19(9-17(20)22(21)27)15-5-7-28-12-15/h1-13H

Standard InChI Key:  NTHOVVGBWASJDT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 33  0  0  0  0  0  0  0  0999 V2000
    7.8197   -9.8723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5248   -9.4634    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2334   -9.8687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2342  -10.6877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9427  -11.0948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6510  -10.6840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6462   -9.8618    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9371   -9.4585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5266  -11.1008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8171  -10.6887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2059  -11.2360    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5376  -11.9865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3538  -11.9028    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8976  -12.5090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6414  -13.2862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2400  -12.9458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6938  -12.3407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3604  -11.0920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4490  -11.9043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2490  -12.0711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6549  -11.3618    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   12.1056  -10.7567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9906  -13.7262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1849  -13.8974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9319  -14.6794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4836  -15.2907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2915  -15.1149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5407  -14.3332    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  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 23  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3910848

   ---

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: 379.45

Molecular Weight (Monoisotopic): 379.0892

AlogP: 5.25

#Rotatable Bonds: 2

Polar Surface Area: 56.49

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 4.77

CX LogP: 4.05

CX LogD: 4.05

Aromatic Rings: 6

Heavy Atoms: 28

QED Weighted: 0.41

Np Likeness Score: -1.71

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