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

ID: ALA5208499

PubChem CID: 156780199

Max Phase: Preclinical

Molecular Formula: C17H13N5O2

Molecular Weight: 319.32

Names and Identifiers

Canonical SMILES:  C=CCn1cc(C#N)c2ccc(NC(=O)c3cc(=O)[nH]cn3)cc21

Standard InChI:  InChI=1S/C17H13N5O2/c1-2-5-22-9-11(8-18)13-4-3-12(6-15(13)22)21-17(24)14-7-16(23)20-10-19-14/h2-4,6-7,9-10H,1,5H2,(H,21,24)(H,19,20,23)

Standard InChI Key:  RUOZGWDXBRRPKV-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
    0.4828    0.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1974    0.9790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9093    0.5671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9093   -0.2579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1992   -0.6697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4828   -0.2616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6922   -0.5038    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1842    0.1636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7135    0.8173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9271    1.6144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1406    2.4115    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2317   -0.6743    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9464   -0.2616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6610   -0.6743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9464    0.5634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6610   -1.4994    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3756   -1.9120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0902   -1.4994    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0903   -0.6742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3756   -0.2616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8049   -0.2616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9058   -1.3009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6757   -1.5964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8049   -2.4115    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  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA5208499

   ---

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: 319.32

Molecular Weight (Monoisotopic): 319.1069

AlogP: 2.03

#Rotatable Bonds: 4

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: 1.41

CX LogD: 1.37

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.72

Np Likeness Score: -1.71

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