3-[4-(3-aminopropoxy)-3-bromophenyl]-N-[2-(4-chlorophenyl)ethyl]-2-hydroxyiminopropanamide hydrochloride

ID: ALA537643

Max Phase: Preclinical

Molecular Formula: C20H24BrCl2N3O3

Molecular Weight: 468.78

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cl.NCCCOc1ccc(C/C(=N/O)C(=O)NCCc2ccc(Cl)cc2)cc1Br

Standard InChI:  InChI=1S/C20H23BrClN3O3.ClH/c21-17-12-15(4-7-19(17)28-11-1-9-23)13-18(25-27)20(26)24-10-8-14-2-5-16(22)6-3-14;/h2-7,12,27H,1,8-11,13,23H2,(H,24,26);1H/b25-18-;

Standard InChI Key:  PWSYEAWKFWMEHL-OYEQKBROSA-N

Molfile:  

     RDKit          2D

 29 29  0  0  0  0  0  0  0  0999 V2000
    7.6894   -2.2522    0.0000 Cl  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
   -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 C   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
   -1.2925   -3.7494    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2872   -4.9494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8912   -5.2578    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9336   -3.1588    0.0000 O   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
   -5.1872   -7.5117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4854   -8.2648    0.0000 C   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 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5951    3.0039    0.0000 C   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
    3.8912    5.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9291    5.8600    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4855   -9.7649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7845  -10.5149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0836   -9.7649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0836   -8.2649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7846   -7.5149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1228  -10.3650    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  2  7  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 10 13  1  0
 10 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
  2 18  1  0
  3 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 17 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 17 28  1  0
 27 28  2  0
 26 29  1  0
M  END

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: 468.78

Molecular Weight (Monoisotopic): 467.0611

AlogP: 3.56

#Rotatable Bonds: 10

Polar Surface Area: 96.94

Molecular Species: BASE

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.64

CX Basic pKa: 9.96

CX LogP: 2.79

CX LogD: 1.76

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.21

Np Likeness Score: -0.14

References

1. Zhu G, Yang F, Balachandran R, Höök P, Vallee RB, Curran DP, Day BW..  (2006)  Synthesis and biological evaluation of purealin and analogues as cytoplasmic dynein heavy chain inhibitors.,  49  (6): [PMID:16539395] [10.1021/jm051030l]

Source

Source(1):

• Scientific Literature