1-(4-(3-Cyano-6-(3-methoxyphenyl)-2-oxo-1,2-dihydropyridin-4-yl)phenyl)-3-ethylurea

ID: ALA3394155

PubChem CID: 118725940

Max Phase: Preclinical

Molecular Formula: C22H20N4O3

Molecular Weight: 388.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCNC(=O)Nc1ccc(-c2cc(-c3cccc(OC)c3)[nH]c(=O)c2C#N)cc1

Standard InChI:  InChI=1S/C22H20N4O3/c1-3-24-22(28)25-16-9-7-14(8-10-16)18-12-20(26-21(27)19(18)13-23)15-5-4-6-17(11-15)29-2/h4-12H,3H2,1-2H3,(H,26,27)(H2,24,25,28)

Standard InChI Key:  YOURKDRSECYPCZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
    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
    1.5548   -3.6021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8933   -3.7570    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8912   -5.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9292   -5.8600    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
    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
   -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
   -3.9015    3.7484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6012    3.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5987    1.5004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8967    0.7484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1969    1.4963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1993    2.9963    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9034    4.9484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4954    0.7438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4955   -0.7562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7945   -1.5062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0936   -0.7562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0936    0.7438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7945    1.4938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7976   -3.0071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8377   -3.6056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3027    3.7530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2644    4.3546    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  5  6  1  0
  4  5  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
  7 12  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 13 18  1  0
 13 19  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 20 25  2  0
 26 27  1  0
 22 26  1  0
 17 20  1  0
 28 29  3  0
 14 28  1  0
 10 15  1  0
  1  7  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3394155

   ---

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: 388.43

Molecular Weight (Monoisotopic): 388.1535

AlogP: 3.73

#Rotatable Bonds: 5

Polar Surface Area: 107.01

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.99

CX Basic pKa: ┄

CX LogP: 1.97

CX LogD: 1.53

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.62

Np Likeness Score: -1.51

References

1. Naik M, Raichurkar A, Bandodkar BS, Varun BV, Bhat S, Kalkhambkar R, Murugan K, Menon R, Bhat J, Paul B, Iyer H, Hussein S, Tucker JA, Vogtherr M, Embrey KJ, McMiken H, Prasad S, Gill A, Ugarkar BG, Venkatraman J, Read J, Panda M..  (2015)  Structure guided lead generation for M. tuberculosis thymidylate kinase (Mtb TMK): discovery of 3-cyanopyridone and 1,6-naphthyridin-2-one as potent inhibitors.,  58  (2): [PMID:25486447] [10.1021/jm5012947]

Source

Source(1):

• Scientific Literature