N4-(2-(isopropylsulfonyl)phenyl)-N2-(2-methoxyphenyl)-7Hpyrrolo-[2,3-d]pyrimidine-2,4-diamine

ID: ALA4061742

PubChem CID: 121320413

Max Phase: Preclinical

Molecular Formula: C22H23N5O3S

Molecular Weight: 437.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccccc1Nc1nc(Nc2ccccc2S(=O)(=O)C(C)C)c2cc[nH]c2n1

Standard InChI:  InChI=1S/C22H23N5O3S/c1-14(2)31(28,29)19-11-7-5-9-17(19)24-21-15-12-13-23-20(15)26-22(27-21)25-16-8-4-6-10-18(16)30-3/h4-14H,1-3H3,(H3,23,24,25,26,27)

Standard InChI Key:  SGKJYFBLBQTTQE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
   13.6791   -8.2737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0919   -8.9825    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   14.5003   -8.2712    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5418  -11.8659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2512  -11.4605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9582  -11.8745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9564  -12.6918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2491  -13.1007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5343  -12.6846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6640  -13.0964    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3755  -12.6868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0911  -13.0964    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.7943  -12.6868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7943  -11.8674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0911  -11.4619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3755  -11.8674    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.5686  -12.9353    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.5686  -11.6174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0475  -12.2729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0911  -10.6369    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3762  -10.2252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3762   -9.4059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6730   -8.9962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9615   -9.4059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9615  -10.2252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6730  -10.6349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8117   -9.3871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8228  -10.2095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5121   -8.9763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2478  -13.9179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5395  -14.3254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  4  9  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 11 16  2  0
 18 19  2  0
 17 19  1  0
 13 17  1  0
 14 18  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 21 26  2  0
 27 28  1  0
 27 29  1  0
  2 27  1  0
 22  2  1  0
 20 21  1  0
 15 20  1  0
 10 11  1  0
  7 10  1  0
  8 30  1  0
 30 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4061742

   ---

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: 437.53

Molecular Weight (Monoisotopic): 437.1522

AlogP: 4.64

#Rotatable Bonds: 7

Polar Surface Area: 109.00

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.63

CX Basic pKa: 4.40

CX LogP: 4.43

CX LogD: 4.43

Aromatic Rings: 4

Heavy Atoms: 31

QED Weighted: 0.39

Np Likeness Score: -1.23

References

1. Sugimoto Y, Sawant DB, Fisk HA, Mao L, Li C, Chettiar S, Li PK, Darby MV, Brueggemeier RW..  (2017)  Novel pyrrolopyrimidines as Mps1/TTK kinase inhibitors for breast cancer.,  25  (7): [PMID:28259529] [10.1016/j.bmc.2017.02.030]

Source

Source(1):

• Scientific Literature