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

ID: ALA4168388

PubChem CID: 145954816

Max Phase: Preclinical

Molecular Formula: C20H17BrN2O2S

Molecular Weight: 429.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1/C(=C/c2cccc(OCc3ccc(Br)cc3)c2)N=C2SCCCN12

Standard InChI:  InChI=1S/C20H17BrN2O2S/c21-16-7-5-14(6-8-16)13-25-17-4-1-3-15(11-17)12-18-19(24)23-9-2-10-26-20(23)22-18/h1,3-8,11-12H,2,9-10,13H2/b18-12-

Standard InChI Key:  WGRUZPUCMYXYQH-PDGQHHTCSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
   24.0617   -5.5691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8812   -5.5702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2881   -4.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8808   -4.1555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0581   -4.1583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6508   -4.8634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1095   -4.8618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5220   -5.5737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.3433   -5.5739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7484   -6.2865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5690   -6.2871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9827   -5.5748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5658   -4.8605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7466   -4.8634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9762   -4.1515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7975   -4.1488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2788   -4.8050    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.2744   -3.4787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0566   -3.7286    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.0572   -4.5481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7639   -4.9571    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   32.4744   -4.5470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4738   -3.7275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7627   -3.3181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0179   -2.6987    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.8294   -4.8658    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  3  7  1  0
  7  8  1  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  9  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 20  2  0
 19 18  1  0
 18 16  1  0
 19 20  1  0
 19 24  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 18 25  2  0
  6 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4168388

   ---

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: 429.34

Molecular Weight (Monoisotopic): 428.0194

AlogP: 4.70

#Rotatable Bonds: 4

Polar Surface Area: 41.90

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.74

CX LogD: 4.74

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.66

Np Likeness Score: -1.28

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