3-[2-(3-aminopropoxy)-3,5-dibromophenyl]-2-hydroxyimino-N-[2-(1H-indol-3-yl)ethyl]propanamide hydrochloride

ID: ALA557359

Max Phase: Preclinical

Molecular Formula: C22H25Br2ClN4O3

Molecular Weight: 552.27

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cl.NCCCOc1c(Br)cc(Br)cc1C/C(=N/O)C(=O)NCCc1c[nH]c2ccccc12

Standard InChI:  InChI=1S/C22H24Br2N4O3.ClH/c23-16-10-15(21(18(24)12-16)31-9-3-7-25)11-20(28-30)22(29)26-8-6-14-13-27-19-5-2-1-4-17(14)19;/h1-2,4-5,10,12-13,27,30H,3,6-9,11,25H2,(H,26,29);1H/b28-20-;

Standard InChI Key:  JDFRVIUGYNEEFH-ZOIOKFABSA-N

Molfile:  

     RDKit          2D

 32 33  0  0  0  0  0  0  0  0999 V2000
   14.0276    4.9876    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.9249    9.5665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9224   10.6823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4549   10.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9898    8.9460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9923    7.8301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4598    8.1405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4606    7.0220    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9933    5.5958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9941    4.4773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5268    3.0511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3270    2.1569    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5241    6.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0553    6.0958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5870    4.6698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1182    4.3614    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3875    3.7758    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0564    7.2160    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8813    6.9729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6500    2.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1812    2.6271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138    1.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0990    9.8148    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    6.6529   11.2647    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    1.7138   -1.2033    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5889    0.0182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028    1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028   -1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917   -0.7475    0.0000 C   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
  2 23  1  0
  4 24  1  0
 22 26  2  0
 25 26  1  0
 22 27  1  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 25 32  1  0
 27 32  2  0
 31 32  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: 552.27

Molecular Weight (Monoisotopic): 550.0215

AlogP: 4.15

#Rotatable Bonds: 10

Polar Surface Area: 112.73

Molecular Species: BASE

HBA: 5

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.53

CX Basic pKa: 9.95

CX LogP: 3.05

CX LogD: 2.08

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.13

Np Likeness Score: 0.02

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