2-{2-[4-(4-Pyrrolidin-1-yl-butoxy)-phenyl]-vinyl}-benzothiazole hydrochloride hydrate

ID: ALA1202629

PubChem CID: 49860315

Max Phase: Preclinical

Molecular Formula: C23H29ClN2O2S

Molecular Weight: 378.54

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C(=C/c1nc2ccccc2s1)\c1ccc(OCCCCN2CCCC2)cc1.Cl.O

Standard InChI:  InChI=1S/C23H26N2OS.ClH.H2O/c1-2-8-22-21(7-1)24-23(27-22)14-11-19-9-12-20(13-10-19)26-18-6-5-17-25-15-3-4-16-25;;/h1-2,7-14H,3-6,15-18H2;1H;1H2/b14-11+;;

Standard InChI Key:  ORFVGRWWQMDZIB-IVKCLRODSA-N

Molfile:  

     RDKit          2D

 29 30  0  0  0  0  0  0  0  0999 V2000
   20.3233    1.3007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0864    0.1373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8201    1.4465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3208    1.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0545    2.7759    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.5332    2.9357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8233    4.4074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5132    5.1381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4135    4.1179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5857    0.1172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8519   -1.1920    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3512   -1.2122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6160   -2.5196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1161   -2.5366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3513   -1.2462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8506   -1.2602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0872    0.0320    0.0000 C   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
    1.7138    1.2033    0.0000 N   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
    1.7138   -1.2033    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.0866    0.0613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5865    0.0783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8233    1.3007    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9  5  1  0
  2 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 25 26  1  0
 26 18  1  0
 15 27  1  0
 27 28  2  0
 28 12  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: 378.54

Molecular Weight (Monoisotopic): 378.1766

AlogP: 5.72

#Rotatable Bonds: 8

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: 9.92

CX LogP: 5.52

CX LogD: 3.05

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.47

Np Likeness Score: -1.43

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