2-(4-(8-(thiophen-3-yl)-1H-imidazo[4,5-c]quinolin-1-yl)phenyl)acetonitrile

ID: ALA3928698

PubChem CID: 134141902

Max Phase: Preclinical

Molecular Formula: C22H14N4S

Molecular Weight: 366.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#CCc1ccc(-n2cnc3cnc4ccc(-c5ccsc5)cc4c32)cc1

Standard InChI:  InChI=1S/C22H14N4S/c23-9-7-15-1-4-18(5-2-15)26-14-25-21-12-24-20-6-3-16(11-19(20)22(21)26)17-8-10-27-13-17/h1-6,8,10-14H,7H2

Standard InChI Key:  LAPRMRQFLNUIQX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    2.0079   -1.4195    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7165   -1.8247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7173   -2.6437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4258   -3.0508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1341   -2.6400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1293   -1.8179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4202   -1.4145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0097   -3.0568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3003   -2.6447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6890   -3.1920    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0207   -3.9425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8369   -3.8589    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3807   -4.4651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1245   -5.2422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6689   -5.8506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4696   -5.6831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7231   -4.9018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1770   -4.2967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0156   -6.2912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7621   -7.0680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5091   -7.8432    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8435   -3.0480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9321   -3.8603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7321   -4.0271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1380   -3.3178    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.5887   -2.7128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 10  2  0
  9  4  2  0
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  2  1  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
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  8  3  1  0
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 17 20  1  0
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 21 22  3  0
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 27 23  2  0
  6 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3928698

   ---

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: 366.45

Molecular Weight (Monoisotopic): 366.0939

AlogP: 5.37

#Rotatable Bonds: 3

Polar Surface Area: 54.50

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.87

CX Basic pKa: 2.77

CX LogP: 4.42

CX LogD: 4.42

Aromatic Rings: 5

Heavy Atoms: 27

QED Weighted: 0.43

Np Likeness Score: -1.55

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