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

ID: ALA3928098

PubChem CID: 134142091

Max Phase: Preclinical

Molecular Formula: C19H12N8

Molecular Weight: 352.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  c1nc2ccc(-n3cnc4cnc5cnc(-c6cn[nH]c6)cc5c43)cc2[nH]1

Standard InChI:  InChI=1S/C19H12N8/c1-2-14-16(23-9-22-14)3-12(1)27-10-24-18-8-21-17-7-20-15(4-13(17)19(18)27)11-5-25-26-6-11/h1-10H,(H,22,23)(H,25,26)

Standard InChI Key:  KTWDMLLGYHAUNG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 32  0  0  0  0  0  0  0  0999 V2000
    1.1583   -2.2699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8634   -1.8611    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5721   -2.2663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5728   -3.0854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2814   -3.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9896   -3.0816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9849   -2.2595    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2758   -1.8561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8652   -3.4984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1558   -3.0863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5446   -3.6336    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8763   -4.3841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6924   -4.3005    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2363   -4.9067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9800   -5.6838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5786   -5.3434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0325   -4.7383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3329   -6.1266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5235   -6.2951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4336   -7.1169    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1875   -7.4564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7432   -6.8443    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7031   -3.4846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7917   -4.2970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5917   -4.4638    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9975   -3.7544    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4483   -3.1494    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
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 27 23  2  0
  6 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3928098

   ---

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: 352.36

Molecular Weight (Monoisotopic): 352.1185

AlogP: 3.24

#Rotatable Bonds: 2

Polar Surface Area: 100.96

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.91

CX Basic pKa: 6.31

CX LogP: 1.70

CX LogD: 1.67

Aromatic Rings: 6

Heavy Atoms: 27

QED Weighted: 0.50

Np Likeness Score: -1.35

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