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

ID: ALA3394894

PubChem CID: 136001903

Max Phase: Preclinical

Molecular Formula: C22H18BrN3O4

Molecular Weight: 468.31

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C22H18BrN3O4/c1-30-19-12-14(11-18(23)20(19)27)13-24-26-22(29)16-7-9-17(10-8-16)25-21(28)15-5-3-2-4-6-15/h2-13,27H,1H3,(H,25,28)(H,26,29)/b24-13+

Standard InChI Key:  VLMHBNNOEWUVNP-ZMOGYAJESA-N

Molfile:  

     RDKit          2D

 30 32  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
    0.0031   -3.0008    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0432   -3.5993    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
   -2.3383    1.3500    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.5972    1.5031    0.0000 C   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
    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
    5.1894    6.0109    0.0000 C   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
    5.1894    7.5110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4884    8.2610    0.0000 C   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
    7.7875    6.0110    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
    9.0888    8.2588    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.3875    7.5066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6887    8.2544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3854    6.3066    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9878    7.5044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2869    8.2545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2869    9.7545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9878   10.5044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6888    9.7544    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
  6  7  1  0
  7  8  1  0
  5  9  1  0
  4 10  1  0
  2 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 15 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 15  1  0
 19 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  2  0
 24 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3394894

   ---

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: 468.31

Molecular Weight (Monoisotopic): 467.0481

AlogP: 4.18

#Rotatable Bonds: 6

Polar Surface Area: 100.02

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.29

CX Basic pKa: 0.76

CX LogP: 4.36

CX LogD: 4.31

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.37

Np Likeness Score: -1.14

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