(6-Chloro-4-((5-methyl-1H-pyrazol-3-yl)amino)quinazolin-2-yl)(4-(methylamino)piperidin-1-yl)methanone

ID: ALA4097984

PubChem CID: 135198764

Max Phase: Preclinical

Molecular Formula: C19H22ClN7O

Molecular Weight: 399.89

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CNC1CCN(C(=O)c2nc(Nc3cc(C)[nH]n3)c3cc(Cl)ccc3n2)CC1

Standard InChI:  InChI=1S/C19H22ClN7O/c1-11-9-16(26-25-11)23-17-14-10-12(20)3-4-15(14)22-18(24-17)19(28)27-7-5-13(21-2)6-8-27/h3-4,9-10,13,21H,5-8H2,1-2H3,(H2,22,23,24,25,26)

Standard InChI Key:  SQNQEVSSPGGWOF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
   12.5589  -12.3513    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.2685  -11.9419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2657  -11.1192    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.5571  -10.7140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8508  -11.9424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8531  -11.1246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1472  -10.7156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4385  -11.1231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4402  -11.9440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1467  -12.3494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7307  -10.7146    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   12.5536   -9.8968    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.2596   -9.4852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0049   -9.8123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5491   -9.2026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1375   -8.4966    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3389   -8.6701    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.3622   -9.2846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9769  -12.3494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9782  -13.1666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6840  -11.9397    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.3907  -12.3528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0956  -11.9466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0985  -11.1290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3904  -10.7194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6792  -11.1272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8072  -10.7220    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.5140  -11.1322    0.0000 C   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
 24 27  1  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4097984

   ---

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: 399.89

Molecular Weight (Monoisotopic): 399.1574

AlogP: 2.88

#Rotatable Bonds: 4

Polar Surface Area: 98.83

Molecular Species: BASE

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.28

CX Basic pKa: 10.34

CX LogP: 2.44

CX LogD: -0.25

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.62

Np Likeness Score: -1.53

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