(2R,3R)-1-(1,3-benzodioxol-5-ylsulfonyl)-3-(5-chloro-2-methoxyphenoxy)-2-methylazetidine

ID: ALA4292781

PubChem CID: 145989859

Max Phase: Preclinical

Molecular Formula: C18H18ClNO6S

Molecular Weight: 411.86

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(Cl)cc1O[C@@H]1CN(S(=O)(=O)c2ccc3c(c2)OCO3)[C@@H]1C

Standard InChI:  InChI=1S/C18H18ClNO6S/c1-11-18(26-17-7-12(19)3-5-14(17)23-2)9-20(11)27(21,22)13-4-6-15-16(8-13)25-10-24-15/h3-8,11,18H,9-10H2,1-2H3/t11-,18-/m1/s1

Standard InChI Key:  JSEMZWQCXWGYNX-ADLMAVQZSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
   17.0953  -18.5369    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5119  -19.2536    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   17.9243  -18.5345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0868  -20.9145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8031  -20.5012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8003  -19.6707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0850  -19.2616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3719  -20.5017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3731  -19.6775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5895  -19.4214    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1040  -20.0876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5876  -20.7552    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.2292  -19.6653    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.4447  -20.4646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2431  -20.2485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0270  -19.4503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9585  -20.6593    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9605  -21.4843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2468  -21.8971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2485  -22.7213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9645  -23.1329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6803  -22.7142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6751  -21.8913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3870  -21.4745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.1039  -21.8827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5349  -23.1352    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   19.4381  -18.7350    0.0000 C   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  6
 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
 16 27  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA4292781

   ---

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: 411.86

Molecular Weight (Monoisotopic): 411.0543

AlogP: 2.92

#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: 3.05

CX LogD: 3.05

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.75

Np Likeness Score: -0.67

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