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

ID: ALA2165441

PubChem CID: 56949917

Max Phase: Preclinical

Molecular Formula: C11H17N3O4

Molecular Weight: 255.27

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C11H17N3O4/c1-2-12-11(15)17-7-9-5-10(18-14-9)16-6-8-3-4-13-8/h5,8,13H,2-4,6-7H2,1H3,(H,12,15)/t8-/m0/s1

Standard InChI Key:  DGVVOJAYZVNQDK-QMMMGPOBSA-N

Molfile:  

     RDKit          2D

 18 19  0  0  0  0  0  0  0  0999 V2000
    4.4374  -25.3205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2624  -25.3205    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5192  -24.5364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8499  -24.0497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1849  -24.5364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2291  -24.1164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4667  -24.1205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7516  -24.5321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0377  -24.1187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8205  -23.3208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0234  -23.5333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2359  -24.3305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9480  -24.5212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9568  -25.3461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6757  -25.7509    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2467  -25.7662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6844  -26.5759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4007  -26.9750    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
 18 17  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2165441

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

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: 255.27

Molecular Weight (Monoisotopic): 255.1219

AlogP: 0.66

#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: ┄

CX Basic pKa: 9.61

CX LogP: -0.14

CX LogD: -2.32

Aromatic Rings: 1

Heavy Atoms: 18

QED Weighted: 0.78

Np Likeness Score: -0.75

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