N4-Cyclohexyl-N2-(2-methoxy-4-morpholinophenyl)-7Hpyrrolo[2,3-d]pyrimidine-2,4-diamine

ID: ALA4076767

PubChem CID: 121320416

Max Phase: Preclinical

Molecular Formula: C23H30N6O2

Molecular Weight: 422.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(N2CCOCC2)ccc1Nc1nc(NC2CCCCC2)c2cc[nH]c2n1

Standard InChI:  InChI=1S/C23H30N6O2/c1-30-20-15-17(29-11-13-31-14-12-29)7-8-19(20)26-23-27-21-18(9-10-24-21)22(28-23)25-16-5-3-2-4-6-16/h7-10,15-16H,2-6,11-14H2,1H3,(H3,24,25,26,27,28)

Standard InChI Key:  YIGQSLKUNKHIBI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 35  0  0  0  0  0  0  0  0999 V2000
    9.8291  -11.4534    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.1218  -11.8623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4107  -11.4483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4146  -10.6275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1239  -10.2221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8346  -10.6382    0.0000 C   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
   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
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  1  6  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
  7 12  2  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
 21 22  2  0
 20 22  1  0
 16 20  1  0
 17 21  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 24 29  1  0
 23 24  1  0
 18 23  1  0
 13 14  1  0
 10 13  1  0
  1  7  1  0
 11 30  1  0
 30 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4076767

   ---

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: 422.53

Molecular Weight (Monoisotopic): 422.2430

AlogP: 4.29

#Rotatable Bonds: 6

Polar Surface Area: 87.33

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.40

CX Basic pKa: 6.61

CX LogP: 4.23

CX LogD: 4.17

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.55

Np Likeness Score: -1.41

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