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

ID: ALA4169536

PubChem CID: 145952824

Max Phase: Preclinical

Molecular Formula: C22H22N2O2S

Molecular Weight: 378.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1/C(=C/c2cccc(OCCCc3ccccc3)c2)N=C2SCCCN12

Standard InChI:  InChI=1S/C22H22N2O2S/c25-21-20(23-22-24(21)12-6-14-27-22)16-18-9-4-11-19(15-18)26-13-5-10-17-7-2-1-3-8-17/h1-4,7-9,11,15-16H,5-6,10,12-14H2/b20-16-

Standard InChI Key:  PLSWADCBNSNPGS-SILNSSARSA-N

Molfile:  

     RDKit          2D

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   12.4813  -10.6482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8898  -11.3601    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7111  -11.3603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1203  -12.0729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9409  -12.0734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3505  -11.3612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9377  -10.6469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1185  -10.6498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3439   -9.9337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1652   -9.9310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6507  -10.5914    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.6463   -9.2610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4285   -9.5108    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.4291  -10.3303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1358  -10.7393    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   18.8463  -10.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8457   -9.5097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1345   -9.1003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3898   -8.4809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2475   -9.9360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6604   -9.2243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4787   -9.2282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8874   -8.5173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4789   -7.8044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6534   -7.8068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2443   -8.5183    0.0000 C   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
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  9  4  1  0
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 15 16  1  0
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 17 18  1  0
 18 19  1  0
 13 20  2  0
  1 21  1  0
 21 22  1  0
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 25 26  1  0
 26 27  2  0
 27 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4169536

   ---

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: 378.50

Molecular Weight (Monoisotopic): 378.1402

AlogP: 4.37

#Rotatable Bonds: 6

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: 4.71

CX LogD: 4.71

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.55

Np Likeness Score: -1.09

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