1-(4-(6-((4-(2-(Cyclopentylamino)-4-methylthiazol-5-yl)-pyrimidin-2-yl)amino)pyridin-3-yl)piperazin-1-yl)ethan-1-one

ID: ALA4099517

PubChem CID: 135286306

Max Phase: Preclinical

Molecular Formula: C24H30N8OS

Molecular Weight: 478.63

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)N1CCN(c2ccc(Nc3nccc(-c4sc(NC5CCCC5)nc4C)n3)nc2)CC1

Standard InChI:  InChI=1S/C24H30N8OS/c1-16-22(34-24(27-16)28-18-5-3-4-6-18)20-9-10-25-23(29-20)30-21-8-7-19(15-26-21)32-13-11-31(12-14-32)17(2)33/h7-10,15,18H,3-6,11-14H2,1-2H3,(H,27,28)(H,25,26,29,30)

Standard InChI Key:  ONRJNVZFOSHIQI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 34 38  0  0  0  0  0  0  0  0999 V2000
   38.7816   -3.1834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.5625   -2.9174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.2367   -3.3929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.8972   -2.8986    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   40.6312   -2.1177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.1066   -1.4434    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   40.7217   -0.7137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.0858    0.0316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.4943    0.6044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.7646    0.2241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.9052   -0.5962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.8063   -2.1293    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   40.2484   -4.2177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.9686   -4.6201    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   40.9803   -5.4450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.6979   -5.8451    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   42.4212   -5.4482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.4390   -4.6234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.1623   -4.2265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.8676   -4.6543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.5909   -4.2574    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   44.6087   -3.4327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.3319   -3.0357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.0373   -3.4636    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   46.7604   -3.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.7351   -2.2421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   47.4659   -3.4946    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   46.0194   -4.2884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.2962   -4.6854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.8498   -5.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.1265   -5.8761    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   40.2717   -5.8676    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.5515   -5.4653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.5398   -4.6403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  7 11  1  0
  5 12  2  0
  2 12  1  0
  3 13  1  0
 13 14  2  0
 14 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  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  2  0
 24 28  1  0
 28 29  1  0
 21 29  1  0
 20 30  1  0
 30 31  2  0
 17 31  1  0
 15 32  2  0
 32 33  1  0
 33 34  2  0
 13 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4099517

   ---

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: 478.63

Molecular Weight (Monoisotopic): 478.2263

AlogP: 4.07

#Rotatable Bonds: 6

Polar Surface Area: 99.17

Molecular Species: NEUTRAL

HBA: 9

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.35

CX Basic pKa: 3.63

CX LogP: 3.06

CX LogD: 3.06

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.55

Np Likeness Score: -1.75

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