(E)-N-(4-(2-(3-bromo-4-hydroxy-5-methoxybenzylidene)-1-methylhydrazinecarbonyl)phenyl)benzamide

ID: ALA3394925

PubChem CID: 137007118

Max Phase: Preclinical

Molecular Formula: C23H20BrN3O4

Molecular Weight: 482.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(/C=N/N(C)C(=O)c2ccc(NC(=O)c3ccccc3)cc2)cc(Br)c1O

Standard InChI:  InChI=1S/C23H20BrN3O4/c1-27(25-14-15-12-19(24)21(28)20(13-15)31-2)23(30)17-8-10-18(11-9-17)26-22(29)16-6-4-3-5-7-16/h3-14,28H,1-2H3,(H,26,29)/b25-14+

Standard InChI Key:  FWLKYGCLWNASQW-AFUMVMLFSA-N

Molfile:  

     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
    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
   -2.5972   -1.5031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5955   -2.7031    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 Br  0  0  0  0  0  0  0  0  0  0  0  0
   12.9879  -10.5043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2870   -9.7543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2869   -8.2543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9879   -7.5043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6888   -8.2543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6889   -9.7543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3875   -7.5065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0888   -8.2588    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.3855   -6.3065    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7875   -7.5110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4885   -8.2610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1895   -7.5109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1894   -6.0109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4885   -5.2610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7876   -6.0110    0.0000 C   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
    3.8933   -3.7570    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8509   -5.8560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5951   -3.0039    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -1.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9336   -3.1588    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
  5  7  1  0
  7  8  1  0
  4  9  1  0
  3 10  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
 15 17  1  0
 17 18  1  0
 17 19  2  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 23 26  1  0
 26 27  1  0
 26 28  2  0
 27 29  1  0
 29 30  2  0
 30  1  1  0
 27 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3394925

   ---

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: 482.33

Molecular Weight (Monoisotopic): 481.0637

AlogP: 4.52

#Rotatable Bonds: 6

Polar Surface Area: 91.23

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.29

CX Basic pKa: 0.67

CX LogP: 4.59

CX LogD: 4.53

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.40

Np Likeness Score: -0.86

References

1. Miknis GF, Stevens SJ, Smith LE, Ostrov DA, Churchill ME..  (2015)  Development of novel Asf1-H3/H4 inhibitors.,  25  (4): [PMID:25582598] [10.1016/j.bmcl.2014.11.067]

2. Miknis, Greg F; Stevens, Sarah J; Smith, Luke E; Ostrov, David A and Churchill, Mair E A.  2015-02-15  Development of novel Asf1-H3/H4 inhibitors.  [PMID:25582598]

Source

Source(1):

• Scientific Literature