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

ID: ALA4168457

PubChem CID: 145953879

Max Phase: Preclinical

Molecular Formula: C25H27ClN2O3S

Molecular Weight: 471.02

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1/C(=C/c2cccc(OCCCCCCOc3ccc(Cl)cc3)c2)N=C2SCCCN12

Standard InChI:  InChI=1S/C25H27ClN2O3S/c26-20-9-11-21(12-10-20)30-14-3-1-2-4-15-31-22-8-5-7-19(17-22)18-23-24(29)28-13-6-16-32-25(28)27-23/h5,7-12,17-18H,1-4,6,13-16H2/b23-18-

Standard InChI Key:  GUVYPTUVBVOIOM-NKFKGCMQSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
   27.9502  -17.9368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3586  -18.6488    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.1799  -18.6490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5892  -19.3616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4097  -19.3621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8193  -18.6498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4065  -17.9356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5873  -17.9385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8128  -17.2224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6341  -17.2197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1195  -17.8801    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.1152  -16.5496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8973  -16.8036    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.8980  -17.6231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6046  -18.0280    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   34.3111  -17.6220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3104  -16.8025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6034  -16.3890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8546  -15.7737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.1289  -17.9366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7163  -17.2247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8950  -17.2245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4866  -16.5126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8954  -15.8050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7167  -15.8052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.1296  -15.0934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9518  -15.0977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3605  -14.3868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9520  -13.6739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1265  -13.6763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7173  -14.3878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3598  -12.9616    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  3  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 14  2  0
 13 12  1  0
 12 10  1  0
 13 14  1  0
 13 18  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 12 19  2  0
  1 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 26  1  0
 29 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4168457

   ---

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: 471.02

Molecular Weight (Monoisotopic): 470.1431

AlogP: 6.03

#Rotatable Bonds: 10

Polar Surface Area: 51.13

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.96

CX LogD: 5.96

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.31

Np Likeness Score: -1.12

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