Dibutyl-(3-{4-[2-(5-chloro-benzothiazol-2-yl)-vinyl]-phenoxy}-propyl)-amine hydrochloride

ID: ALA50136

PubChem CID: 14146377

Max Phase: Preclinical

Molecular Formula: C26H33ClN2OS

Molecular Weight: 457.08

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCN(CCCC)CCCOc1ccc(/C=C/c2nc3cc(Cl)ccc3s2)cc1

Standard InChI:  InChI=1S/C26H33ClN2OS/c1-3-5-16-29(17-6-4-2)18-7-19-30-23-12-8-21(9-13-23)10-15-26-28-24-20-22(27)11-14-25(24)31-26/h8-15,20H,3-7,16-19H2,1-2H3/b15-10+

Standard InChI Key:  DAWKHNZOXMWFDC-XNTDXEJSSA-N

Molfile:  

     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
    0.3875   -3.1000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8667   -3.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3792   -4.4292    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3958   -3.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4000   -4.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6917   -3.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1083   -2.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1042   -4.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1083   -4.5875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8208   -3.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9292   -4.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8917   -5.9125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5792   -4.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8208   -4.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5250   -2.9417    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.3417   -3.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3417   -5.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1667   -5.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1667   -3.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6500   -5.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4042   -4.4875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0625   -5.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8167   -5.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3042   -5.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3000   -6.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1250   -6.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1292   -5.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5375   -7.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5500   -4.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3625   -7.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3750   -4.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  1  1  0
  5  4  2  0
  6  2  1  0
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  8  6  2  0
  9  5  1  0
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 13 18  2  0
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 15 10  1  0
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 17 11  2  0
 18 17  1  0
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 20 23  1  0
 21 13  1  0
 22 20  1  0
 23 21  1  0
 24 12  1  0
 25 12  1  0
 26 25  1  0
 27 24  1  0
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 29 27  1  0
 30 28  1  0
 31 29  1  0
  5  3  1  0
 14  9  2  0
 13 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA50136

   Dibutyl-(3-{4-[2-(5-chloro-benzothiazol-2-yl)-vinyl]-phenoxy}-propyl)-amine;hydrochloride

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: 457.08

Molecular Weight (Monoisotopic): 456.2002

AlogP: 7.79

#Rotatable Bonds: 13

Polar Surface Area: 25.36

Molecular Species: BASE

HBA: 4

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 10.35

CX LogP: 7.85

CX LogD: 5.01

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.25

Np Likeness Score: -1.35

References

1. Sanfilippo PJ, Urbanski M, Press JB, Hajos ZG, Shriver DA, Scott CK..  (1988)  Synthesis of (aryloxy)alkylamines. 1. Novel antisecretory agents with H+K+-ATPase inhibitory activity.,  31  (9): [PMID:2842503] [10.1021/jm00117a018]

Source

Source(1):

• Scientific Literature