3-[2-(3-aminopropoxy)-3,5-dibromophenyl]-N-[2-(4-chlorophenyl)ethyl]-2-hydroxyiminopropanamide hydrochloride

ID: ALA538576

Max Phase: Preclinical

Molecular Formula: C20H23Br2Cl2N3O3

Molecular Weight: 547.68

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cl.NCCCOc1c(Br)cc(Br)cc1C/C(=N/O)C(=O)NCCc1ccc(Cl)cc1

Standard InChI:  InChI=1S/C20H22Br2ClN3O3.ClH/c21-15-10-14(19(17(22)12-15)29-9-1-7-24)11-18(26-28)20(27)25-8-6-13-2-4-16(23)5-3-13;/h2-5,10,12,28H,1,6-9,11,24H2,(H,25,27);1H/b26-18-;

Standard InChI Key:  IGJVTLFRLSJUNT-ZVOSEVRTSA-N

Molfile:  

     RDKit          2D

 30 30  0  0  0  0  0  0  0  0999 V2000
    5.0987   -2.2494    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
   -0.0031   -3.0008    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3039   -3.7494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3070   -5.2502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6078   -5.9988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6103   -7.1988    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6003   -1.4978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8990   -0.7455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2003   -1.4932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4990   -0.7410    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2024   -2.6932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8933    0.7553    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9299    1.3599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8003   -1.4887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0990   -0.7365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4003   -1.4842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6994   -0.7342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.9984   -1.4842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.9984   -2.9842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6994   -3.7342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4004   -2.9843    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
    0.0000    2.7000    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  -14.0377   -3.5842    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
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
  6 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 14 18  2  0
 18 19  1  0
 16 20  1  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
 22 27  1  0
 26 27  2  0
  2 28  1  0
  4 29  1  0
 25 30  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: 547.68

Molecular Weight (Monoisotopic): 544.9716

AlogP: 4.32

#Rotatable Bonds: 10

Polar Surface Area: 96.94

Molecular Species: BASE

HBA: 5

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.41

CX Basic pKa: 9.95

CX LogP: 3.55

CX LogD: 2.66

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.18

Np Likeness Score: -0.16

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