3-methyl-N-{4-[2-(2-oxoindolin-3-yl)hydrazinecarbonyl]phenyl}benzamide

ID: ALA4101154

PubChem CID: 137658669

Max Phase: Preclinical

Molecular Formula: C23H20N4O3

Molecular Weight: 400.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cccc(C(=O)Nc2ccc(C(=O)NNC3C(=O)Nc4ccccc43)cc2)c1

Standard InChI:  InChI=1S/C23H20N4O3/c1-14-5-4-6-16(13-14)21(28)24-17-11-9-15(10-12-17)22(29)27-26-20-18-7-2-3-8-19(18)25-23(20)30/h2-13,20,26H,1H3,(H,24,28)(H,25,30)(H,27,29)

Standard InChI Key:  BMZKKFXAJCTMTM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
   28.0720   -2.3236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0708   -3.1431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7789   -3.5521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4886   -3.1427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4857   -2.3200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7771   -1.9147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7747   -1.0975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3628   -3.5512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6554   -3.1420    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.3622   -4.3684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.9474   -3.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2408   -3.1387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5332   -3.5461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5321   -4.3641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2445   -4.7731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9491   -4.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8246   -4.7731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1167   -4.3649    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.8251   -5.5903    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.4092   -4.7739    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.7013   -4.3656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6165   -3.5533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8171   -3.3838    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.9561   -4.6987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4129   -4.0929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6187   -4.2610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3665   -5.0343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9147   -5.6398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7069   -5.4686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2239   -3.0065    0.0000 O   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
  6  7  1  0
  2  8  1  0
  8  9  1  0
  8 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
 14 17  1  0
 17 18  1  0
 17 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 25  1  0
 24 21  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 24  1  0
 22 30  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4101154

   ---

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: 400.44

Molecular Weight (Monoisotopic): 400.1535

AlogP: 3.18

#Rotatable Bonds: 5

Polar Surface Area: 99.33

Molecular Species: NEUTRAL

HBA: 4

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.43

CX Basic pKa: 1.55

CX LogP: 3.23

CX LogD: 3.23

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.49

Np Likeness Score: -1.20

References

1. Morgillo F, Amendola G, Della Corte CM, Giacomelli C, Botta L, Di Maro S, Messere A, Ciaramella V, Taliani S, Marinelli L, Trincavelli ML, Martini C, Novellino E, Ciardiello F, Cosconati S..  (2017)  Dual MET and SMO Negative Modulators Overcome Resistance to EGFR Inhibitors in Human Nonsmall Cell Lung Cancer.,  60  (17): [PMID:28787156] [10.1021/acs.jmedchem.7b00794]

Source

Source(1):

• Scientific Literature