4-(6-(5-chloro-2-fluorophenyl)-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-N-cyclopropylnicotinamide

ID: ALA4483492

PubChem CID: 155540539

Max Phase: Preclinical

Molecular Formula: C22H17ClFN5O

Molecular Weight: 421.86

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(NC1CC1)c1cnccc1Nc1cc(-c2cc(Cl)ccc2F)nc2[nH]ccc12

Standard InChI:  InChI=1S/C22H17ClFN5O/c23-12-1-4-17(24)15(9-12)20-10-19(14-5-8-26-21(14)29-20)28-18-6-7-25-11-16(18)22(30)27-13-2-3-13/h1,4-11,13H,2-3H2,(H,27,30)(H2,25,26,28,29)

Standard InChI Key:  LJLGIVAKWSPARG-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    3.0640  -20.3867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7720  -20.7957    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7702  -19.1583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4788  -19.5636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4791  -20.3867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2621  -20.6409    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7458  -19.9748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2617  -19.3090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7678  -18.3411    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0589  -17.9346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0598  -17.1182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3517  -16.7118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6442  -17.1225    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6493  -17.9439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3579  -18.3466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3578  -20.7950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6502  -20.3841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9426  -20.7915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9415  -21.6096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6539  -22.0186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3585  -21.6088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0670  -22.0161    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.7672  -16.7091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4752  -17.1171    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7666  -15.8919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1826  -16.7080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9966  -16.7063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5875  -15.9989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2354  -20.3820    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
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 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
  2 17  1  0
 22 23  1  0
 12 24  1  0
 24 25  1  0
 24 26  2  0
 25 27  1  0
 28 27  1  0
 29 28  1  0
 27 29  1  0
 19 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4483492

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 421.86

Molecular Weight (Monoisotopic): 421.1106

AlogP: 5.05

#Rotatable Bonds: 5

Polar Surface Area: 82.70

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.97

CX Basic pKa: 6.64

CX LogP: 5.06

CX LogD: 5.00

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.42

Np Likeness Score: -1.36

References

1. Wang H, Lawson JD, Scorah N, Kamran R, Hixon MS, Atienza J, Dougan DR, Sabat M..  (2016)  Design, synthesis and optimization of novel Alk5 (activin-like kinase 5) inhibitors.,  26  (17): [PMID:27460209] [10.1016/j.bmcl.2016.07.030]

Source

Source(1):

• Scientific Literature