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

ID: ALA4172931

PubChem CID: 145951404

Max Phase: Preclinical

Molecular Formula: C21H20N2O2S

Molecular Weight: 364.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(COc2cccc(/C=C3\N=C4SCCCN4C3=O)c2)cc1

Standard InChI:  InChI=1S/C21H20N2O2S/c1-15-6-8-16(9-7-15)14-25-18-5-2-4-17(12-18)13-19-20(24)23-10-3-11-26-21(23)22-19/h2,4-9,12-13H,3,10-11,14H2,1H3/b19-13-

Standard InChI Key:  GYHAYDDOOBGCGG-UYRXBGFRSA-N

Molfile:  

     RDKit          2D

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   35.4528   -5.0532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2724   -5.0543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6793   -4.3457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2719   -3.6396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4493   -3.6424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0419   -4.3475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.5006   -4.3459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9132   -5.0578    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.7345   -5.0580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.1396   -5.7706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.9601   -5.7711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.3739   -5.0589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.9569   -4.3446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.1377   -4.3475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.3673   -3.6355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.1886   -3.6329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.6741   -4.2891    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   41.6697   -2.9628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.4478   -3.2126    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   42.4484   -4.0321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.1550   -4.4412    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   43.8656   -4.0311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.8650   -3.2116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.1538   -2.8022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.4091   -2.1828    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.2206   -4.3499    0.0000 C   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
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 13 14  2  0
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 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:

   

   ALA4172931

   ---

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: 364.47

Molecular Weight (Monoisotopic): 364.1245

AlogP: 4.25

#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: 4.49

CX LogD: 4.49

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.76

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