4-(((1S,3S)-3-Hydroxy-2,2-dimethylcylobutyl)amino)-2-(((4-(trifluoromethyl)pyridin-3-yl)methyl)amino)pyrimidine-5-carbonitrile

ID: ALA4873812

PubChem CID: 118182830

Max Phase: Preclinical

Molecular Formula: C18H19F3N6O

Molecular Weight: 392.39

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC1(C)[C@@H](Nc2nc(NCc3cnccc3C(F)(F)F)ncc2C#N)C[C@@H]1O

Standard InChI:  InChI=1S/C18H19F3N6O/c1-17(2)13(5-14(17)28)26-15-10(6-22)8-24-16(27-15)25-9-11-7-23-4-3-12(11)18(19,20)21/h3-4,7-8,13-14,28H,5,9H2,1-2H3,(H2,24,25,26,27)/t13-,14-/m0/s1

Standard InChI Key:  QHLWNCNFYOUHJB-KBPBESRZSA-N

Molfile:  

 
     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
   22.0064   -4.3790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7163   -4.7876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7152   -3.9685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1804   -8.2214    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   18.9729   -8.4361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7625   -7.6425    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   23.2228   -6.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5139   -7.2132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8046   -6.8049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0998   -7.2138    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.1002   -8.0310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8053   -8.4393    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.5142   -8.0304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9275   -6.3953    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.3913   -8.4399    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.3917   -9.2571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6832  -10.4791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6828   -9.6619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9735   -9.2537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2687   -9.6626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2691  -10.4798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9743  -10.8881    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.8042   -5.9877    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.6806   -8.0276    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   22.5117   -5.5788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2975   -5.7910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5087   -5.0016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2162   -4.5927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  5  4  1  0
  6  5  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
  8 13  2  0
  7 14  3  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 17 22  2  0
 19  5  1  0
 16 18  1  0
 15 16  1  0
 11 15  1  0
  9 23  1  0
  5 24  1  0
 25 23  1  6
 25 26  1  0
 26 27  1  0
 27  2  1  0
  2 25  1  0
 27 28  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4873812

   4-[[(1S,3S)-3-hydroxy-2,2-dimethylcyclobutyl]amino]-2-[[4-(trifluoromethyl)pyridin-3-yl]methylamino]pyrimidine-5-carbonitrile

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: 392.39

Molecular Weight (Monoisotopic): 392.1572

AlogP: 2.95

#Rotatable Bonds: 5

Polar Surface Area: 106.75

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.57

CX LogP: 1.86

CX LogD: 1.86

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.72

Np Likeness Score: -0.78

References

1. Papa P, Whitefield B, Mortensen DS, Cashion D, Huang D, Torres E, Parnes J, Sapienza J, Hansen J, Correa M, Delgado M, Harris R, Hegde S, Norris S, Bahmanyar S, Plantevin-Krenitsky V, Liu Z, Leftheris K, Kulkarni A, Bennett B, Hur EM, Ringheim G, Khambatta G, Chan H, Muir J, Blease K, Burnett K, LeBrun L, Morrison L, Celeridad M, Khattri R, Cathers BE..  (2021)  Discovery of the Selective Protein Kinase C-θ Kinase Inhibitor, CC-90005.,  64  (16.0): [PMID:34355886] [10.1021/acs.jmedchem.1c00388]

Source

Source(1):

• Scientific Literature