8-cyclopentyl-6-hydroxy-2-((4-(methylsulfonyl)phenyl)amino)pteridin-7(8H)-one

ID: ALA5290919

Max Phase: Preclinical

Molecular Formula: C18H19N5O4S

Molecular Weight: 401.45

Names and Identifiers

Canonical SMILES:  CS(=O)(=O)c1ccc(Nc2ncc3nc(O)c(=O)n(C4CCCC4)c3n2)cc1

Standard InChI:  InChI=1S/C18H19N5O4S/c1-28(26,27)13-8-6-11(7-9-13)20-18-19-10-14-15(22-18)23(12-4-2-3-5-12)17(25)16(24)21-14/h6-10,12H,2-5H2,1H3,(H,21,24)(H,19,20,22)

Standard InChI Key:  SLMIKKOWKMOEMM-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
    0.4133   -0.2231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1278    0.1891    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8398   -0.2228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8398   -1.0479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1297   -1.4597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4133   -1.0516    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5543    0.1897    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2691   -0.2228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2691   -1.0480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5543   -1.4605    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9837    0.1897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9837   -1.4605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3012    0.1894    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0159   -0.2231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5543    1.0149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8871    1.4997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1420    2.2841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9668    2.2841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2216    1.4997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0161   -1.0484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7290   -1.4591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4438   -1.0464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4453   -0.2253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7335    0.1911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1585   -1.4589    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1585   -2.2841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5718   -0.7430    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9837   -1.4589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  1  6  1  0
  6  5  2  0
  3  7  1  0
  8  7  1  0
  9  8  1  0
 10  9  2  0
  4 10  1  0
  8 11  2  0
  9 12  1  0
  1 13  1  0
 13 14  1  0
 15  7  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 15  1  0
 20 14  2  0
 21 20  1  0
 22 21  2  0
 23 22  1  0
 24 23  2  0
 14 24  1  0
 22 25  1  0
 25 26  1  0
 25 27  2  0
 25 28  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA5290919

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 401.45

Molecular Weight (Monoisotopic): 401.1158

AlogP: 2.15

#Rotatable Bonds: 4

Polar Surface Area: 127.07

Molecular Species: ACID

HBA: 9

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.76

CX Basic pKa: 0.16

CX LogP: 1.98

CX LogD: -1.52

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.68

Np Likeness Score: -1.26

References

1. Wang X, Ding L, Jiang H, Yuan X, Xiang L, Tang C..  (2023)  Synthesis and biological evaluation of novel pteridin-7(8H)-one derivatives as potent CDK2 inhibitors.,  88  [PMID:37060933] [10.1016/j.bmcl.2023.129284]

Source

Source(1):

• Scientific Literature