5-(5-(1H-imidazol-1-yl)-3-methyl-1-phenyl-1H-pyrazol-4-yl)-7-amino-2,4-dioxo-2,3,4,5-tetrahydro-1H-pyrano[2,3-d]pyrimidine-6-carbonitrile

ID: ALA5270268

Max Phase: Preclinical

Molecular Formula: C21H16N8O3

Molecular Weight: 428.41

Names and Identifiers

Canonical SMILES:  Cc1nn(-c2ccccc2)c(-n2ccnc2)c1C1C(C#N)=C(N)Oc2[nH]c(=O)[nH]c(=O)c21

Standard InChI:  InChI=1S/C21H16N8O3/c1-11-14(15-13(9-22)17(23)32-19-16(15)18(30)25-21(31)26-19)20(28-8-7-24-10-28)29(27-11)12-5-3-2-4-6-12/h2-8,10,15H,23H2,1H3,(H2,25,26,30,31)

Standard InChI Key:  MSMOXPRRTALCEH-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 32 36  0  0  0  0  0  0  0  0999 V2000
    2.5011   -3.2097    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7866   -2.7971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0719   -3.2097    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -2.7971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3574   -3.2097    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0721   -2.7971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7866   -3.2096    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0721   -1.9719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3574   -1.5592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3574   -0.2009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3100    0.2839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1069    0.0704    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4024   -0.6562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2259   -0.6562    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4394    0.1402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7477    0.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0551    1.0687    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4675    1.7831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2961    1.7831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7042    2.4996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2924    3.2097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4671    3.2097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0552    2.4978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7700    1.0687    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0249    0.2839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8218    0.0704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -1.9719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0719   -1.5592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0719   -0.7342    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7866   -1.9719    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7866   -1.5593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5011   -1.1468    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  1  0
  5  4  1  0
  6  5  1  0
  6  7  1  0
  8  6  2  0
  8  9  1  0
  9 10  1  0
 11 10  2  0
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 15 14  1  0
 16 15  2  0
 12 16  1  0
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 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 18  2  0
 24 17  1  0
 25 24  2  0
 25 10  1  0
 25 26  1  0
 27  9  1  0
  4 27  2  0
 27 28  1  0
 28 29  2  0
 30 28  1  0
  2 30  1  0
 31  8  1  0
 31 32  3  0
M  END

Alternative Forms

1. Parent:

   

   ALA5270268

   ---

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: 428.41

Molecular Weight (Monoisotopic): 428.1345

AlogP: 0.96

#Rotatable Bonds: 3

Polar Surface Area: 160.40

Molecular Species: NEUTRAL

HBA: 9

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.38

CX Basic pKa: 5.86

CX LogP: 0.56

CX LogD: 0.51

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.44

Np Likeness Score: -1.83

References

1. Elattar KM, El-Khateeb AY, Hamed SE..  (2022)  Insights into the recent progress in the medicinal chemistry of pyranopyrimidine analogs.,  13  (5.0): [PMID:35694689] [10.1039/d2md00076h]

Source

Source(1):

• Scientific Literature