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

ID: ALA3394921

PubChem CID: 118726357

Max Phase: Preclinical

Molecular Formula: C23H20BrN3O4

Molecular Weight: 482.33

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C23H20BrN3O4/c1-31-20-14-15(13-19(24)21(20)28)11-12-25-27-23(30)17-7-9-18(10-8-17)26-22(29)16-5-3-2-4-6-16/h2-10,12-14,28H,11H2,1H3,(H,26,29)(H,27,30)/b25-12+

Standard InChI Key:  HXGGEEUUJXMVEQ-BRJLIKDPSA-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 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
   -3.6375   -0.9049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8933   -3.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8934   -5.2570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1924   -6.0071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4914   -5.2571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4915   -3.7571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1925   -3.0071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7927   -6.0049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0914   -5.2527    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7948   -7.2049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3927   -6.0004    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6914   -5.2482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.9927   -5.9960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.2914   -5.2437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.5931   -5.9892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -16.8895   -5.2348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -16.8844   -3.7348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.5828   -2.9892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.2863   -3.7437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.5745   -1.4884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -14.5324   -0.8935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -17.9215   -3.1312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -17.9308   -5.8312    0.0000 Br  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
  7  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 10  1  0
 13 16  1  0
 16 17  1  0
 16 18  2  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
 26 28  1  0
 28 29  1  0
 25 30  1  0
 24 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3394921

   ---

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: 4.37

#Rotatable Bonds: 7

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: 8.62

CX Basic pKa: 0.89

CX LogP: 4.13

CX LogD: 4.10

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.34

Np Likeness Score: -0.75

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