N-(3-cyano-1-methyl-1H-indol-5-yl)-2-methyl-6-oxo-1,6-dihydropyrimidine-4-carboxamide

ID: ALA5202914

PubChem CID: 168293957

Max Phase: Preclinical

Molecular Formula: C20H19N5O2

Molecular Weight: 361.41

Names and Identifiers

Canonical SMILES:  Cc1nc(C(=O)Nc2ccc3c(C#N)cn(C4CCCC4)c3c2)cc(=O)[nH]1

Standard InChI:  InChI=1S/C20H19N5O2/c1-12-22-17(9-19(26)23-12)20(27)24-14-6-7-16-13(10-21)11-25(18(16)8-14)15-4-2-3-5-15/h6-9,11,15H,2-5H2,1H3,(H,24,27)(H,22,23,26)

Standard InChI Key:  CJEAXKVMWTZHGT-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    1.2317    1.1419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9435    0.7300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9435   -0.0951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2335   -0.5069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5171   -0.0988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7265   -0.3410    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2186    0.3265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7477    0.9802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9613    1.7772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1749    2.5743    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1975   -0.5114    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9121   -0.0988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6267   -0.5114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9121    0.7263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6267   -1.3366    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3413   -1.7492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0560   -1.3366    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0560   -0.5114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3414   -0.0988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7706   -0.0988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9401   -1.1381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7371   -1.3517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7706   -2.1932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0174   -2.4787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4999   -1.8307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3413   -2.5743    0.0000 C   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
  6  5  2  0
  1  6  1  0
  4  7  1  0
  7  8  1  0
  9  8  2  0
  3  9  1  0
 10  9  1  0
 10 11  3  0
  6 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 16 14  1  0
 17 16  2  0
 18 17  1  0
 19 18  1  0
 20 19  1  0
 14 20  2  0
 19 21  2  0
  7 22  1  0
 23 22  1  0
 23 24  1  0
 24 25  1  0
 26 25  1  0
 22 26  1  0
 17 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5202914

   ---

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: 361.41

Molecular Weight (Monoisotopic): 361.1539

AlogP: 3.27

#Rotatable Bonds: 3

Polar Surface Area: 103.57

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.22

CX Basic pKa: ┄

CX LogP: 2.09

CX LogD: 2.03

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.75

Np Likeness Score: -1.59

References

1. Zhang B, Duan Y, Yang Y, Mao Q, Lin F, Gao J, Dai X, Zhang P, Li Q, Li J, Dai R, Wang S..  (2022)  Design, synthesis, and biological evaluation of N-(3-cyano-1H-indol-5/6-yl)-6-oxo-1,6-dihydropyrimidine-4-carboxamides and 5-(6-oxo-1,6-dihydropyrimidin-2-yl)-1H-indole-3-carbonitriles as novel xanthine oxidase inhibitors.,  227  [PMID:34688012] [10.1016/j.ejmech.2021.113928]

Source

Source(1):

• Scientific Literature