4-(6-Chloro-4-((5-methyl-1H-pyrazol-3-yl)amino)quinazoline-2-carbonyl)piperazin-2-one

ID: ALA4095155

PubChem CID: 135198805

Max Phase: Preclinical

Molecular Formula: C17H16ClN7O2

Molecular Weight: 385.82

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(Nc2nc(C(=O)N3CCNC(=O)C3)nc3ccc(Cl)cc23)n[nH]1

Standard InChI:  InChI=1S/C17H16ClN7O2/c1-9-6-13(24-23-9)21-15-11-7-10(18)2-3-12(11)20-16(22-15)17(27)25-5-4-19-14(26)8-25/h2-3,6-7H,4-5,8H2,1H3,(H,19,26)(H2,20,21,22,23,24)

Standard InChI Key:  DCJXIFWOSUVWRA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
   21.6140  -21.2290    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.3237  -20.8196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3209  -19.9969    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.6122  -19.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9060  -20.8200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9083  -20.0023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2023  -19.5932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4936  -20.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4953  -20.8217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2018  -21.2270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7859  -19.5923    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   21.6087  -18.7745    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.3147  -18.3628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0600  -18.6899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6043  -18.0803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1926  -17.3743    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.3941  -17.5477    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.4173  -18.1622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0320  -21.2271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0333  -22.0443    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.7391  -20.8174    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.4458  -21.2305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1507  -20.8242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1537  -20.0067    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.4455  -19.5970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7344  -20.0049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8575  -21.2344    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  6  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10  5  2  0
  8 11  1  0
  4 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 13  2  0
 15 18  1  0
  2 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 21 26  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 23 27  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4095155

   ---

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: 385.82

Molecular Weight (Monoisotopic): 385.1054

AlogP: 1.63

#Rotatable Bonds: 3

Polar Surface Area: 115.90

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.20

CX Basic pKa: 3.12

CX LogP: 1.75

CX LogD: 1.75

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.63

Np Likeness Score: -1.75

References

1. Hao C, Zhao F, Song H, Guo J, Li X, Jiang X, Huan R, Song S, Zhang Q, Wang R, Wang K, Pang Y, Liu T, Lu T, Huang W, Wang J, Lin B, He Z, Li H, Li F, Zhao D, Cheng M..  (2018)  Structure-Based Design of 6-Chloro-4-aminoquinazoline-2-carboxamide Derivatives as Potent and Selective p21-Activated Kinase 4 (PAK4) Inhibitors.,  61  (1): [PMID:29190083] [10.1021/acs.jmedchem.7b01342]

Source

Source(1):

• Scientific Literature