2-{2-[4-(3-Imidazol-1-yl-propoxy)-phenyl]-vinyl}-benzothiazole hydrochloride

ID: ALA1202659

PubChem CID: 49860341

Max Phase: Preclinical

Molecular Formula: C21H20ClN3OS

Molecular Weight: 361.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C(=C/c1nc2ccccc2s1)\c1ccc(OCCCn2ccnc2)cc1.Cl

Standard InChI:  InChI=1S/C21H19N3OS.ClH/c1-2-5-20-19(4-1)23-21(26-20)11-8-17-6-9-18(10-7-17)25-15-3-13-24-14-12-22-16-24;/h1-2,4-12,14,16H,3,13,15H2;1H/b11-8+;

Standard InChI Key:  JMWCTPNJWIFGPH-YGCVIUNWSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
   20.1156    0.0766    0.0000 Cl  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
   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
   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 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.1668    2.6899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5985    2.2426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6156    0.7427    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.1943    0.2630    0.0000 C   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  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
 18 19  1  0
 19 11  1  0
  8 20  1  0
 20 21  2  0
 21  5  1  0
  2 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 23  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: 361.47

Molecular Weight (Monoisotopic): 361.1249

AlogP: 5.13

#Rotatable Bonds: 7

Polar Surface Area: 39.94

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 6.53

CX LogP: 4.49

CX LogD: 4.45

Aromatic Rings: 4

Heavy Atoms: 26

QED Weighted: 0.43

Np Likeness Score: -1.67

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