US9452998, 89

ID: ALA3987185

PubChem CID: 118873270

Max Phase: Preclinical

Molecular Formula: C24H27F3N8O3

Molecular Weight: 532.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOCC1(N)CCN(c2cccnc2NC(=O)c2nc(-c3ncccc3OC(F)(F)F)cnc2N)CC1

Standard InChI:  InChI=1S/C24H27F3N8O3/c1-2-37-14-23(29)7-11-35(12-8-23)16-5-3-10-31-21(16)34-22(36)19-20(28)32-13-15(33-19)18-17(6-4-9-30-18)38-24(25,26)27/h3-6,9-10,13H,2,7-8,11-12,14,29H2,1H3,(H2,28,32)(H,31,34,36)

Standard InChI Key:  IUQRWIKPYXRDAP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 38 41  0  0  0  0  0  0  0  0999 V2000
   -1.0761   -5.0822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0372   -4.4818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0368   -2.9810    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2626   -2.2300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3233   -0.1247    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5987    1.5004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8967    0.7484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1969    1.4963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1993    2.9963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9014    3.7484    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6012    3.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3042    3.7556    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3088    5.2564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3501    5.8529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0118    6.0116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2885    5.2638    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5863    6.0160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5838    7.5160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2835    8.2638    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0142    7.5117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0544    8.1100    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8873    5.2678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1840    6.0219    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4854    5.2761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4903    3.7762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1937    3.0219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8922    3.7677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5965    3.0104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6036    1.5096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5676    0.9040    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.6458    0.9148    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.6098    0.3096    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11  5  1  0
  9 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
 26 27  1  0
 23 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 28  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 35 37  1  0
 35 38  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3987185

   ---

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: 532.53

Molecular Weight (Monoisotopic): 532.2158

AlogP: 3.00

#Rotatable Bonds: 8

Polar Surface Area: 154.40

Molecular Species: BASE

HBA: 10

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 13.20

CX Basic pKa: 9.60

CX LogP: 2.99

CX LogD: 0.85

Aromatic Rings: 3

Heavy Atoms: 38

QED Weighted: 0.39

Np Likeness Score: -0.82

References

1.  (2016)  Protein kinase C inhibitors and methods of their use, 

Source

Source(1):

• BindingDB Database