N-Cyclopentyl-4-methyl-5-(2-((5-(4-(methylsulfonyl)piperazin-1-yl)pyridin-2-yl)amino)pyrimidin-4-yl)thiazol-2-amine

ID: ALA4069886

PubChem CID: 135296342

Max Phase: Preclinical

Molecular Formula: C23H30N8O2S2

Molecular Weight: 514.68

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1nc(NC2CCCC2)sc1-c1ccnc(Nc2ccc(N3CCN(S(C)(=O)=O)CC3)cn2)n1

Standard InChI:  InChI=1S/C23H30N8O2S2/c1-16-21(34-23(26-16)27-17-5-3-4-6-17)19-9-10-24-22(28-19)29-20-8-7-18(15-25-20)30-11-13-31(14-12-30)35(2,32)33/h7-10,15,17H,3-6,11-14H2,1-2H3,(H,26,27)(H,24,25,28,29)

Standard InChI Key:  ZIWFXQFVSGOWAZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 35 39  0  0  0  0  0  0  0  0999 V2000
   33.4194   -9.4527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.8352  -10.1681    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   34.2467   -9.4502    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.1215  -10.5794    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.1169  -11.4044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4000  -11.8129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4093  -10.1629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6925  -10.5714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6880  -11.3964    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.9711  -11.8050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9666  -12.6299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2498  -13.0384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2590  -11.3884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5422  -11.7969    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.5377  -12.6219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8209  -13.0304    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.1012  -12.6341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3931  -13.0575    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.6725  -12.6560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6599  -11.8311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3680  -11.4077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3554  -10.5828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6807  -10.1081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9000  -10.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9236   -9.3197    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.7485   -9.3071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2232   -8.6323    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.8762   -7.8839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0667   -7.7247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9679   -6.9056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7164   -6.5586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2777   -7.1632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0154  -10.0878    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   28.0887  -11.8093    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.5490  -10.5865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  4  7  1  0
  7  8  1  0
  8  9  1  0
  6  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 10 13  2  0
 13 14  1  0
 14 15  2  0
 12 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 23 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 28 32  1  0
 26 33  1  0
 22 33  1  0
 21 34  2  0
 17 34  1  0
  2 35  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4069886

   ---

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: 514.68

Molecular Weight (Monoisotopic): 514.1933

AlogP: 3.48

#Rotatable Bonds: 7

Polar Surface Area: 116.24

Molecular Species: NEUTRAL

HBA: 10

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.35

CX Basic pKa: 3.63

CX LogP: 2.55

CX LogD: 2.55

Aromatic Rings: 3

Heavy Atoms: 35

QED Weighted: 0.49

Np Likeness Score: -1.93

References

1. Tadesse S, Yu M, Mekonnen LB, Lam F, Islam S, Tomusange K, Rahaman MH, Noll B, Basnet SK, Teo T, Albrecht H, Milne R, Wang S..  (2017)  Highly Potent, Selective, and Orally Bioavailable 4-Thiazol-N-(pyridin-2-yl)pyrimidin-2-amine Cyclin-Dependent Kinases 4 and 6 Inhibitors as Anticancer Drug Candidates: Design, Synthesis, and Evaluation.,  60  (5): [PMID:28156111] [10.1021/acs.jmedchem.6b01670]

Source

Source(1):

• Scientific Literature