5-[(2(S)-Azetidinyl)methoxy]-3-[(N-phenylcarbamoyloxy)-methyl]isoxazole

ID: ALA2165440

PubChem CID: 56949915

Max Phase: Preclinical

Molecular Formula: C15H17N3O4

Molecular Weight: 303.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Nc1ccccc1)OCc1cc(OC[C@@H]2CCN2)on1

Standard InChI:  InChI=1S/C15H17N3O4/c19-15(17-11-4-2-1-3-5-11)21-10-13-8-14(22-18-13)20-9-12-6-7-16-12/h1-5,8,12,16H,6-7,9-10H2,(H,17,19)/t12-/m0/s1

Standard InChI Key:  LRAKKOBBQWUEQH-LBPRGKRZSA-N

Molfile:  

     RDKit          2D

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   20.8544  -22.3046    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.6795  -22.3046    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.9363  -21.5205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2670  -21.0337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6020  -21.5205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6462  -21.1004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8836  -21.1045    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1687  -21.5161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4547  -21.1027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2375  -20.3048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4404  -20.5174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6529  -21.3145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.3651  -21.5052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.3739  -22.3301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0928  -22.7350    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.6639  -22.7503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.1016  -23.5600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3897  -23.9766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3982  -24.8008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1176  -25.2064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8299  -24.7819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8179  -23.9591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  1  1  0
  3  6  1  0
  5  7  1  0
  7  8  1  0
  9  8  1  1
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12  9  1  0
  6 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2165440

   [5-[[(2S)-azetidin-2-yl]methoxy]-1,2-oxazol-3-yl]methyl N-phenylcarbamate

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: 303.32

Molecular Weight (Monoisotopic): 303.1219

AlogP: 2.16

#Rotatable Bonds: 6

Polar Surface Area: 85.62

Molecular Species: BASE

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.03

CX Basic pKa: 9.61

CX LogP: 1.52

CX LogD: -0.66

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.85

Np Likeness Score: -0.94

References

1. Yu LF, Tückmantel W, Eaton JB, Caldarone B, Fedolak A, Hanania T, Brunner D, Lukas RJ, Kozikowski AP..  (2012)  Identification of novel α4β2-nicotinic acetylcholine receptor (nAChR) agonists based on an isoxazole ether scaffold that demonstrate antidepressant-like activity.,  55  (2): [PMID:22148173] [10.1021/jm201301h]

Source

Source(1):

• Scientific Literature