3-[4-(3-aminopropoxy)-3-bromophenyl]-2-hydroxyimino-N-[2-(1H-indol-3-yl)ethyl]propanamide hydrochloride

ID: ALA558971

Max Phase: Preclinical

Molecular Formula: C22H26BrClN4O3

Molecular Weight: 473.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cl.NCCCOc1ccc(C/C(=N/O)C(=O)NCCc2c[nH]c3ccccc23)cc1Br

Standard InChI:  InChI=1S/C22H25BrN4O3.ClH/c23-18-12-15(6-7-21(18)30-11-3-9-24)13-20(27-29)22(28)25-10-8-16-14-26-19-5-2-1-4-17(16)19;/h1-2,4-7,12,14,26,29H,3,8-11,13,24H2,(H,25,28);1H/b27-20-;

Standard InChI Key:  BFJNITIQXYHKER-HNKVEKQCSA-N

Molfile:  

     RDKit          2D

 31 32  0  0  0  0  0  0  0  0999 V2000
   15.7648    7.0318    0.0000 Cl  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
    8.9224   10.6823    0.0000 C   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
    9.4598    8.1405    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
    6.9898    8.9460    0.0000 C   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
    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
    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
    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
    6.6529   11.2647    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    9.3907   12.1083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8595   12.4166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3277   13.8425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7966   14.1509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1710   15.2910    0.0000 N   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
    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
  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
  2 17  1  0
  3 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 16 23  1  0
 23 25  2  0
 24 25  1  0
 23 26  1  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 24 31  1  0
 26 31  2  0
 30 31  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: 473.37

Molecular Weight (Monoisotopic): 472.1110

AlogP: 3.39

#Rotatable Bonds: 10

Polar Surface Area: 112.73

Molecular Species: BASE

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.77

CX Basic pKa: 9.97

CX LogP: 2.29

CX LogD: 1.18

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.16

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