6-((3-(5-chloro-2-methoxyphenoxy)-1-azetidinyl)sulfonyl)-1,3-benzoxazol-2(3H)-one

ID: ALA4284872

PubChem CID: 145991039

Max Phase: Preclinical

Molecular Formula: C17H15ClN2O6S

Molecular Weight: 410.84

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(Cl)cc1OC1CN(S(=O)(=O)c2ccc3[nH]c(=O)oc3c2)C1

Standard InChI:  InChI=1S/C17H15ClN2O6S/c1-24-14-5-2-10(18)6-16(14)25-11-8-20(9-11)27(22,23)12-3-4-13-15(7-12)26-17(21)19-13/h2-7,11H,8-9H2,1H3,(H,19,21)

Standard InChI Key:  WSLXBZIFAXISNU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
   29.5996   -2.2999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.0163   -3.0166    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   30.4286   -2.2974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.5911   -4.6776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3074   -4.2643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3046   -3.4338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5892   -3.0247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8762   -4.2648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8774   -3.4404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0939   -3.1845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.6083   -3.8507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0919   -4.5183    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.7335   -3.4284    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.9490   -4.2277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7474   -4.0116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5314   -3.2133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4629   -4.4224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.4649   -5.2474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7511   -5.6601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7528   -6.4844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4688   -6.8960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1847   -6.4773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1794   -5.6544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8915   -5.2376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.6083   -5.6458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0392   -6.8982    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   25.7833   -3.8495    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  8  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  9  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12  8  1  0
  6  2  1  0
  2 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 13  1  0
 15 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
 23 24  1  0
 24 25  1  0
 20 26  1  0
 11 27  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4284872

   ---

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: 410.84

Molecular Weight (Monoisotopic): 410.0339

AlogP: 2.23

#Rotatable Bonds: 5

Polar Surface Area: 101.84

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.23

CX Basic pKa: ┄

CX LogP: 2.36

CX LogD: 2.36

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.69

Np Likeness Score: -1.18

References

1. Chakka N, Andrews KL, Berry LM, Bregman H, Gunaydin H, Huang L, Guzman-Perez A, Plant MH, Simard JR, Gingras J, DiMauro EF..  (2017)  Applications of parallel synthetic lead hopping and pharmacophore-based virtual screening in the discovery of efficient glycine receptor potentiators.,  137  [PMID:28575722] [10.1016/j.ejmech.2017.05.036]

Source

Source(1):

• Scientific Literature