(Z)-5-(3-((4-Chlorobenzyl)oxy)benzylidene)-2-(methylthio)-1,5-dihydro-4H-imidazole-4-one

ID: ALA4163505

PubChem CID: 145958034

Max Phase: Preclinical

Molecular Formula: C18H15ClN2O2S

Molecular Weight: 358.85

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CSC1=NC(=O)/C(=C/c2cccc(OCc3ccc(Cl)cc3)c2)N1

Standard InChI:  InChI=1S/C18H15ClN2O2S/c1-24-18-20-16(17(22)21-18)10-13-3-2-4-15(9-13)23-11-12-5-7-14(19)8-6-12/h2-10H,11H2,1H3,(H,20,21,22)/b16-10-

Standard InChI Key:  WQJGSVBTMYODME-YBEGLDIGSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
    3.3182  -11.0211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1378  -11.0223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5447  -10.3137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1373   -9.6076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3147   -9.6104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9073  -10.3154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3660  -10.3139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7786  -11.0258    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5999  -11.0260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0050  -11.7386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8255  -11.7391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2393  -11.0269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8223  -10.3126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0031  -10.3155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2327   -9.6035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0540   -9.6008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5353  -10.2571    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5310   -8.9308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3132   -9.1806    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.3138  -10.0001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0204  -10.4091    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.2745   -8.1508    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0860  -10.3179    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   11.0195  -11.2263    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
 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  1  0
 19 18  1  0
 18 16  1  0
 19 20  2  0
 20 21  1  0
 18 22  2  0
  6 23  1  0
 21 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4163505

   ---

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: 358.85

Molecular Weight (Monoisotopic): 358.0543

AlogP: 4.11

#Rotatable Bonds: 4

Polar Surface Area: 50.69

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.23

CX LogD: 4.23

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.84

Np Likeness Score: -0.94

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