4-((((cis)-3-Hydroxycyclobutyl)methyl)amino)-6-(((4-(trifluoromethyl)pyridin-3-yl)methyl)amino)nicotinonitrile

ID: ALA4878438

Max Phase: Preclinical

Molecular Formula: C18H18F3N5O

Molecular Weight: 377.37

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  N#Cc1cnc(NCc2cnccc2C(F)(F)F)cc1NC[C@H]1C[C@@H](O)C1

Standard InChI:  InChI=1S/C18H18F3N5O/c19-18(20,21)15-1-2-23-8-13(15)10-26-17-5-16(12(6-22)9-25-17)24-7-11-3-14(27)4-11/h1-2,5,8-9,11,14,27H,3-4,7,10H2,(H2,24,25,26)/t11-,14+

Standard InChI Key:  JTFXUGXTGVGJAZ-VDISTLRHSA-N

Molfile:  

 
     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
    1.8242  -13.3062    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.6414  -13.3062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2328  -12.5985    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.9151  -11.7519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1993  -12.1455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5014  -11.7262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7856  -12.1197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7719  -12.9367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4698  -13.3602    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1856  -12.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6309  -11.3542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0561  -13.3344    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0423  -14.1514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3128  -15.3620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3265  -14.5450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6286  -14.1257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9128  -14.5234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8990  -15.3404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5970  -15.7597    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3568  -12.9121    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.5171  -10.9091    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2325  -10.5142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2481   -9.6971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8379   -9.1351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2712   -8.5463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6824   -9.1130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2869   -7.7293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  5 10  2  0
  4 11  3  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 14 19  2  0
 16  2  1  0
 13 15  1  0
 12 13  1  0
  8 12  1  0
  2 20  1  0
  6 21  1  0
 21 22  1  0
 23 22  1  1
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 23  1  0
 25 27  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4878438

   ---

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: 377.37

Molecular Weight (Monoisotopic): 377.1463

AlogP: 3.16

#Rotatable Bonds: 6

Polar Surface Area: 93.86

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.56

CX LogP: 1.37

CX LogD: 1.32

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.72

Np Likeness Score: -0.95

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