3-(5-cyano-2,6-dihydroxypyrimidin-4-ylamino)-N-methylbenzamide

ID: ALA3622451

PubChem CID: 52233987

Max Phase: Preclinical

Molecular Formula: C13H11N5O3

Molecular Weight: 285.26

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CNC(=O)c1cccc(Nc2nc(O)nc(O)c2C#N)c1

Standard InChI:  InChI=1S/C13H11N5O3/c1-15-11(19)7-3-2-4-8(5-7)16-10-9(6-14)12(20)18-13(21)17-10/h2-5H,1H3,(H,15,19)(H3,16,17,18,20,21)

Standard InChI Key:  DDXKJYKMVXEWKI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
    1.2990   -0.7500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3383    1.3500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.7000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5988   -1.5004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6380   -2.1004    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5973    1.5031    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5951    3.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8916    3.7585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8864    5.2585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5847    6.0040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2883    5.2495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2935    3.7495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1820    6.0160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2243    5.4214    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1747    7.5168    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2106    8.1226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  2  7  1  0
  6  8  1  0
  9 10  3  0
  5  9  1  0
  4 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
 14 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3622451

   3-[(5-cyano-2,4-dioxo-1H-pyrimidin-6-yl)amino]-N-methylbenzamide

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 285.26

Molecular Weight (Monoisotopic): 285.0862

AlogP: 0.86

#Rotatable Bonds: 3

Polar Surface Area: 131.16

Molecular Species: NEUTRAL

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.02

CX Basic pKa: ┄

CX LogP: 1.68

CX LogD: 1.68

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.66

Np Likeness Score: -1.58

References

1. Pala N, Stevaert A, Dallocchio R, Dessì A, Rogolino D, Carcelli M, Sanna V, Sechi M, Naesens L..  (2015)  Virtual Screening and Biological Validation of Novel Influenza Virus PA Endonuclease Inhibitors.,  6  (8): [PMID:26288686] [10.1021/acsmedchemlett.5b00109]

Source

Source(1):

• Scientific Literature