5-amino-2-((4-methoxypyridin-2-yl)amino)-7-(methylthio)pyrazolo[1,5-a]pyrimidine-3,6-dicarbonitrile

ID: ALA5274868

Max Phase: Preclinical

Molecular Formula: C15H12N8OS

Molecular Weight: 352.38

Names and Identifiers

Canonical SMILES:  COc1ccnc(Nc2nn3c(SC)c(C#N)c(N)nc3c2C#N)c1

Standard InChI:  InChI=1S/C15H12N8OS/c1-24-8-3-4-19-11(5-8)20-13-10(7-17)14-21-12(18)9(6-16)15(25-2)23(14)22-13/h3-5H,1-2H3,(H2,18,21)(H,19,20,22)

Standard InChI Key:  RMSJQJOHBDAMEL-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   -1.7473    2.2237    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1639    1.6404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5806    1.0570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2264    1.2286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6390    0.5140    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0868   -0.0990    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6668    0.2365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3817   -0.1762    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3817   -1.0017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6696   -1.4137    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6696   -2.2392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3799   -2.6512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0966   -2.2430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8110   -2.6554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5255   -2.2430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0966   -1.4141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4676    0.5140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8756    1.2309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4635    1.9410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6382    1.9410    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8760    2.6554    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7005    1.2309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5255    1.2309    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8801   -0.2001    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.7051   -0.2001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  3  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  3  7  1  0
  8  7  1  0
  9  8  1  0
 10  9  1  0
 11 10  2  0
 12 11  1  0
 13 12  2  0
 13 14  1  0
 14 15  1  0
 16 13  1  0
  9 16  2  0
  5 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
  4 20  1  0
 19 21  1  0
 18 22  1  0
 22 23  3  0
 17 24  1  0
 24 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5274868

   ---

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: 352.38

Molecular Weight (Monoisotopic): 352.0855

AlogP: 1.92

#Rotatable Bonds: 4

Polar Surface Area: 137.94

Molecular Species: NEUTRAL

HBA: 10

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.70

CX Basic pKa: 4.72

CX LogP: 2.10

CX LogD: 2.10

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.53

Np Likeness Score: -1.16

References

1. Hammouda MM, Gaffer HE, Elattar KM..  (2022)  Insights into the medicinal chemistry of heterocycles integrated with a pyrazolo[1,5-a]pyrimidine scaffold.,  13  (10.0): [PMID:36325400] [10.1039/d2md00192f]

Source

Source(1):

• Scientific Literature