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

ID: ALA3394895

PubChem CID: 136001911

Max Phase: Preclinical

Molecular Formula: C20H22BrN3O4

Molecular Weight: 448.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCC(=O)Nc1ccc(C(=O)N/N=C/c2cc(Br)c(O)c(OC)c2)cc1

Standard InChI:  InChI=1S/C20H22BrN3O4/c1-3-4-5-18(25)23-15-8-6-14(7-9-15)20(27)24-22-12-13-10-16(21)19(26)17(11-13)28-2/h6-12,26H,3-5H2,1-2H3,(H,23,25)(H,24,27)/b22-12+

Standard InChI Key:  JDYIARKCILFUMT-WSDLNYQXSA-N

Molfile:  

     RDKit          2D

 28 29  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
   12.9874    7.5021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2887    8.2499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3271    7.6485    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
 26 24  1  0
 26 27  1  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3394895

   ---

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: 448.32

Molecular Weight (Monoisotopic): 447.0794

AlogP: 4.06

#Rotatable Bonds: 8

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: 0.88

CX LogP: 4.10

CX LogD: 4.05

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.42

Np Likeness Score: -1.21

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