N4-((1R,2R)-2-(dimethylamino)cyclopentyl)-N2-(4-((S)-N-methylethylsulfonimidoyl)phenyl)-5-(trifluoromethyl)pyrimidine-2,4-diamine

ID: ALA2448536

PubChem CID: 70692073

Max Phase: Preclinical

Molecular Formula: C21H29F3N6OS

Molecular Weight: 470.57

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC[S+]([O-])(=NC)c1ccc(Nc2ncc(C(F)(F)F)c(N[C@@H]3CCC[C@H]3N(C)C)n2)cc1

Standard InChI:  InChI=1S/C21H29F3N6OS/c1-5-32(31,25-2)15-11-9-14(10-12-15)27-20-26-13-16(21(22,23)24)19(29-20)28-17-7-6-8-18(17)30(3)4/h9-13,17-18H,5-8H2,1-4H3,(H2-,25,26,27,28,29,31)/t17-,18-,32?/m1/s1

Standard InChI Key:  MIZGEGJKPOLHOH-XZQBWAKSSA-N

Molfile:  

     RDKit          2D

 32 34  0  0  0  0  0  0  0  0999 V2000
   14.2037   -6.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4892   -5.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7748   -6.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7748   -7.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4892   -7.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2037   -7.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0603   -7.5667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.0603   -8.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7748   -8.8042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.7748   -9.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0603  -10.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3458   -9.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3458   -8.8042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.9182   -5.9167    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   14.5057   -5.2023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6327   -5.5042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3307   -6.6312    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.0603  -10.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0603  -11.6917    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   11.2353  -10.8667    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   12.8853  -10.8667    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   13.4892  -10.0417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.4892  -10.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1567  -11.3517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9017  -12.1363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0767  -12.1363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8218  -11.3517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9413  -11.0967    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.5544  -11.6488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1128  -10.2898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1557   -6.6312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6807   -5.2023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  2  0
 14 16  1  0
  7  8  1  0
 14 17  2  0
 11 18  1  0
  8  9  2  0
 18 19  1  0
  4  5  1  0
 18 20  1  0
  9 10  1  0
 18 21  1  0
  2  3  1  0
 10 22  1  0
 10 11  2  0
 23 22  1  1
 23 24  1  0
  5  6  2  0
 11 12  1  0
  6  1  1  0
 12 13  2  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 23  1  0
 13  8  1  0
 24 28  1  6
  1  2  2  0
 28 29  1  0
 14  1  1  0
 28 30  1  0
  4  7  1  0
 17 31  1  0
 14 15  1  0
 15 32  1  0
M  CHG  2  14   1  16  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2448536

   CID 70692073

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: 470.57

Molecular Weight (Monoisotopic): 470.2076

AlogP: 4.61

#Rotatable Bonds: 7

Polar Surface Area: 88.50

Molecular Species: BASE

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.32

CX Basic pKa: 9.31

CX LogP: 3.69

CX LogD: 1.78

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.57

Np Likeness Score: -0.88

References

1. Walker DP, Zawistoski MP, McGlynn MA, Li JC, Kung DW, Bonnette PC, Baumann A, Buckbinder L, Houser JA, Boer J, Mistry A, Han S, Xing L, Guzman-Perez A..  (2009)  Sulfoximine-substituted trifluoromethylpyrimidine analogs as inhibitors of proline-rich tyrosine kinase 2 (PYK2) show reduced hERG activity.,  19  (12): [PMID:19428251] [10.1016/j.bmcl.2009.04.093]

Source

Source(1):

• Scientific Literature