(Z)-5-(3-((4-Chlorobenzyl)oxy)benzylidene)-2-((4-chlorobenzyl)thio)-3,5-dihydro-4H-imidazole-4-one

ID: ALA4170355

PubChem CID: 145955833

Max Phase: Preclinical

Molecular Formula: C24H18Cl2N2O2S

Molecular Weight: 469.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1NC(SCc2ccc(Cl)cc2)=N/C1=C\c1cccc(OCc2ccc(Cl)cc2)c1

Standard InChI:  InChI=1S/C24H18Cl2N2O2S/c25-19-8-4-16(5-9-19)14-30-21-3-1-2-18(12-21)13-22-23(29)28-24(27-22)31-15-17-6-10-20(26)11-7-17/h1-13H,14-15H2,(H,27,28,29)/b22-13-

Standard InChI Key:  QAEUIFPDAOXNND-XKZIYDEJSA-N

Molfile:  

     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
    2.5010  -16.3040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3206  -16.3051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7275  -15.5965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3201  -14.8904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4975  -14.8932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0901  -15.5983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5488  -15.5967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9614  -16.3086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7827  -16.3088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1878  -17.0214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0084  -17.0220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4221  -16.3097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0051  -15.5954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1859  -15.5984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4155  -14.8864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2368  -14.8837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7181  -15.5399    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138  -14.2136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4960  -14.4635    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4966  -15.2830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2032  -15.6920    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.4573  -13.4336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2688  -15.6007    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   10.2023  -16.5092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9096  -16.9186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9046  -17.7358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6110  -18.1451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3202  -17.7372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3185  -16.9158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6114  -16.5102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0280  -18.1456    0.0000 Cl  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
 20 21  1  0
 18 22  2  0
  6 23  1  0
 21 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 25  1  0
 28 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4170355

   ---

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: 469.39

Molecular Weight (Monoisotopic): 468.0466

AlogP: 6.33

#Rotatable Bonds: 6

Polar Surface Area: 50.69

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.75

CX Basic pKa: ┄

CX LogP: 6.79

CX LogD: 6.79

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.43

Np Likeness Score: -1.05

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