1-(1,3-benzodioxol-5-ylsulfonyl)-3-(5-fluoro-2-methoxyphenoxy)azetidine

ID: ALA4285964

PubChem CID: 145990853

Max Phase: Preclinical

Molecular Formula: C17H16FNO6S

Molecular Weight: 381.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(F)cc1OC1CN(S(=O)(=O)c2ccc3c(c2)OCO3)C1

Standard InChI:  InChI=1S/C17H16FNO6S/c1-22-14-4-2-11(18)6-17(14)25-12-8-19(9-12)26(20,21)13-3-5-15-16(7-13)24-10-23-15/h2-7,12H,8-10H2,1H3

Standard InChI Key:  ITSWPWUIGSLYHD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
   15.7581   -9.9207    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1748  -10.6373    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   16.5871   -9.9181    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7495  -12.2983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4660  -11.8850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4631  -11.0545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7477  -10.6454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0348  -11.8855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0360  -11.0611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2524  -10.8052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7668  -11.4714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2503  -12.1390    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8921  -11.0491    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.1076  -11.8484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9058  -11.6323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6899  -10.8340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6213  -12.0431    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6233  -12.8681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9097  -13.2808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9113  -14.1051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6274  -14.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3431  -14.0980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3380  -13.2752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0499  -12.8583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.7669  -13.2665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1976  -14.5189    0.0000 F   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
M  END

Alternative Forms

1. Parent:

   

   ALA4285964

   ---

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: 381.38

Molecular Weight (Monoisotopic): 381.0682

AlogP: 2.01

#Rotatable Bonds: 5

Polar Surface Area: 74.30

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.17

CX LogD: 2.17

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.79

Np Likeness Score: -1.14

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