(Z)-2-(3-(2-(4-Chlorophenoxy)ethoxy)benzylidene)-6,7-dihydro-2H-imidazo[2,1-b][1,3]thiazin-3(5H)-one

ID: ALA4161619

PubChem CID: 145960178

Max Phase: Preclinical

Molecular Formula: C21H19ClN2O3S

Molecular Weight: 414.91

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1/C(=C/c2cccc(OCCOc3ccc(Cl)cc3)c2)N=C2SCCCN12

Standard InChI:  InChI=1S/C21H19ClN2O3S/c22-16-5-7-17(8-6-16)26-10-11-27-18-4-1-3-15(13-18)14-19-20(25)24-9-2-12-28-21(24)23-19/h1,3-8,13-14H,2,9-12H2/b19-14-

Standard InChI Key:  AIGWIEWLFLLFAA-RGEXLXHISA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
   21.5819  -11.0277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4032  -11.0279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8116  -11.7398    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.6329  -11.7400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0422  -12.4526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8627  -12.4531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2723  -11.7409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8595  -11.0266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0403  -11.0295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2658  -10.3134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0871  -10.3107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5725  -10.9711    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.5682   -9.6448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3504   -9.8946    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.3510  -10.7141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0576  -11.1190    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   28.7682  -10.7131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7676   -9.8936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0564   -9.4800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3117   -8.8648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.1693  -10.3157    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.5822   -9.6081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4006   -9.6120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8092   -8.9011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4008   -8.1882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5752   -8.1906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1661   -8.9021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8086   -7.4759    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 15  2  0
 14 13  1  0
 13 11  1  0
 14 15  1  0
 14 19  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 13 20  2  0
  1 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
 25 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4161619

   ---

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: 414.91

Molecular Weight (Monoisotopic): 414.0805

AlogP: 4.47

#Rotatable Bonds: 6

Polar Surface Area: 51.13

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.50

CX LogD: 4.50

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.52

Np Likeness Score: -1.38

References

1. Schoeder CT, Kaleta M, Mahardhika AB, Olejarz-Maciej A, Łażewska D, Kieć-Kononowicz K, Müller CE..  (2018)  Structure-activity relationships of imidazothiazinones and analogs as antagonists of the cannabinoid-activated orphan G protein-coupled receptor GPR18.,  155  [PMID:29902723] [10.1016/j.ejmech.2018.05.050]

Source

Source(1):

• Scientific Literature