US8846917, I-1

ID: ALA3695214

PubChem CID: 71521971

Max Phase: Preclinical

Molecular Formula: C21H20N6O2S

Molecular Weight: 420.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)S(=O)(=O)c1ccc(-c2cnc(N)c(-c3cn(-c4ccccc4)nn3)n2)cc1

Standard InChI:  InChI=1S/C21H20N6O2S/c1-14(2)30(28,29)17-10-8-15(9-11-17)18-12-23-21(22)20(24-18)19-13-27(26-25-19)16-6-4-3-5-7-16/h3-14H,1-2H3,(H2,22,23)

Standard InChI Key:  GJAQQKJDEHDCCU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
    3.6390   -3.6012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5997   -3.0012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5607   -3.6016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5988   -1.5004    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.6383   -2.0999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6378   -0.9001    0.0000 O   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
    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 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
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   -2.5987    1.5004    0.0000 C   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
   -3.9015    3.7484    0.0000 N   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
   -6.2395    3.5946    0.0000 N   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
   -3.8967    0.7484    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4954    0.7438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8488    1.3606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8489    0.2427    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0948   -1.0540    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6286   -0.7374    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3419    0.3948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0545    1.7091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.5540    1.7484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.3378    0.4695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.6221   -0.8487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1226   -0.8881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  4  6  2  0
  4  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  7  1  0
 10 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 13  1  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 24 20  1  0
 22 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3695214

   5-(4-(isopropylsulfonyl)phenyl)-3-(1-phenyl-1H-1,2,3-triazol-4-yl)pyrazin-2-amine

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: 420.50

Molecular Weight (Monoisotopic): 420.1368

AlogP: 3.16

#Rotatable Bonds: 5

Polar Surface Area: 116.65

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 1.27

CX LogP: 3.38

CX LogD: 3.38

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.53

Np Likeness Score: -1.57

References

1.  (2014)  Compounds useful as inhibitors of ATR kinase, 

2. Knegtel R, Charrier JD, Durrant S, Davis C, O'Donnell M, Storck P, MacCormick S, Kay D, Pinder J, Virani A, Twin H, Griffiths M, Reaper P, Littlewood P, Young S, Golec J, Pollard J..  (2019)  Rational Design of 5-(4-(Isopropylsulfonyl)phenyl)-3-(3-(4-((methylamino)methyl)phenyl)isoxazol-5-yl)pyrazin-2-amine (VX-970, M6620): Optimization of Intra- and Intermolecular Polar Interactions of a New Ataxia Telangiectasia Mutated and Rad3-Related (ATR) Kinase Inhibitor.,  62  (11): [PMID:31074988] [10.1021/acs.jmedchem.9b00426]

Source

Source(2):

• Scientific Literature
• BindingDB Database