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

ID: ALA5206013

PubChem CID: 156780192

Max Phase: Preclinical

Molecular Formula: C22H17N5O3

Molecular Weight: 399.41

Names and Identifiers

Canonical SMILES:  COc1ccc(Cn2cc(C#N)c3cc(NC(=O)c4cc(=O)[nH]cn4)ccc32)cc1

Standard InChI:  InChI=1S/C22H17N5O3/c1-30-17-5-2-14(3-6-17)11-27-12-15(10-23)18-8-16(4-7-20(18)27)26-22(29)19-9-21(28)25-13-24-19/h2-9,12-13H,11H2,1H3,(H,26,29)(H,24,25,28)

Standard InChI Key:  ABWYGBNUWFPWLM-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
   -1.3096    0.3075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5950    0.7198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1168    0.3079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1168   -0.5172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5933   -0.9290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3096   -0.5209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8997   -0.7631    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3917   -0.0955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9210    0.5581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1346    1.3552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3481    2.1522    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1133   -1.5602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9103   -1.7737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4940   -1.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2885   -1.4041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5022   -2.2013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9227   -2.7831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1248   -2.5742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0242    0.7201    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7389    0.3075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4535    0.7201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1681    0.3075    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8827    0.7201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8827    1.5453    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1681    1.9579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4535    1.5453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1681    2.7831    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7389   -0.5176    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2992   -2.4149    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8827   -1.8314    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
  7 12  1  0
 12 13  1  0
 14 13  2  0
 15 14  1  0
 16 15  2  0
 17 16  1  0
 18 17  2  0
 13 18  1  0
  1 19  1  0
 19 20  1  0
 20 21  1  0
 22 21  1  0
 23 22  2  0
 24 23  1  0
 25 24  1  0
 26 25  1  0
 21 26  2  0
 25 27  2  0
 20 28  2  0
 16 29  1  0
 29 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5206013

   ---

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: 399.41

Molecular Weight (Monoisotopic): 399.1331

AlogP: 2.91

#Rotatable Bonds: 5

Polar Surface Area: 112.80

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.36

CX Basic pKa: ┄

CX LogP: 2.25

CX LogD: 2.21

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.54

Np Likeness Score: -1.62

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