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

ID: ALA5202994

PubChem CID: 156780189

Max Phase: Preclinical

Molecular Formula: C19H17N5O2

Molecular Weight: 347.38

Names and Identifiers

Canonical SMILES:  N#Cc1cn(C2CCCC2)c2cc(NC(=O)c3cc(=O)[nH]cn3)ccc12

Standard InChI:  InChI=1S/C19H17N5O2/c20-9-12-10-24(14-3-1-2-4-14)17-7-13(5-6-15(12)17)23-19(26)16-8-18(25)22-11-21-16/h5-8,10-11,14H,1-4H2,(H,23,26)(H,21,22,25)

Standard InChI Key:  JXYHZEQBEJIBKS-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    0.5474    0.6778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2620    1.0901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9739    0.6782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9739   -0.1468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2638   -0.5586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5474   -0.1505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7568   -0.3928    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2488    0.2747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7780    0.9284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9916    1.7255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2052    2.5226    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1671   -0.5632    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8818   -0.1505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5964   -0.5632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8818    0.6745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5964   -1.3883    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3110   -1.8009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0257   -1.3883    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0257   -0.5631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3111   -0.1505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7403   -0.1505    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9704   -1.1898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7403   -1.4854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6972   -2.3091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9005   -2.5226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4513   -1.8308    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
 25 26  1  0
 26 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5202994

   ---

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: 347.38

Molecular Weight (Monoisotopic): 347.1382

AlogP: 2.96

#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: 8.37

CX Basic pKa: ┄

CX LogP: 2.04

CX LogD: 2.00

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.76

Np Likeness Score: -1.41

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