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

ID: ALA4278706

PubChem CID: 145979377

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-/m0/s1

Standard InChI Key:  JSEMZWQCXWGYNX-VOJFVSQTSA-N

Molfile:  

     RDKit          2D

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   29.3962  -18.6961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.8129  -19.4128    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   30.2252  -18.6936    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.3876  -21.0738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1041  -20.6604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1012  -19.8300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3857  -19.4208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6728  -20.6609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6740  -19.8366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8904  -19.5807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.4048  -20.2469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8884  -20.9144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.5302  -19.8245    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.7457  -20.6238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5441  -20.4078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3280  -19.6095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2596  -20.8185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.2615  -21.6435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5478  -22.0564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5494  -22.8806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2655  -23.2922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9813  -22.8735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9762  -22.0506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6881  -21.6338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.4051  -22.0420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8358  -23.2945    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   31.7391  -18.8942    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  1
 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  1
M  END

Alternative Forms

1. Parent:

   

   ALA4278706

   ---

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