3-[(2(S)-Azetidinyl)methoxy]-5-(phenoxymethyl)isoxazole

ID: ALA2165447

PubChem CID: 56949640

Max Phase: Preclinical

Molecular Formula: C14H16N2O3

Molecular Weight: 260.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  c1ccc(OCc2cc(OC[C@@H]3CCN3)no2)cc1

Standard InChI:  InChI=1S/C14H16N2O3/c1-2-4-12(5-3-1)17-10-13-8-14(16-19-13)18-9-11-6-7-15-11/h1-5,8,11,15H,6-7,9-10H2/t11-/m0/s1

Standard InChI Key:  KZONDTNPVHWVKU-NSHDSACASA-N

Molfile:  

     RDKit          2D

 19 21  0  0  0  0  0  0  0  0999 V2000
   12.3877   -6.4668    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.2127   -6.4668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4695   -5.6827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8002   -5.1960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1352   -5.6827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1795   -5.2626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4169   -5.2667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7019   -5.6783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9879   -5.2649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7707   -4.4671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9736   -4.6796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1861   -5.4767    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.8983   -5.6674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6083   -5.2473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3257   -5.6541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0352   -5.2346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0269   -4.4088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3030   -4.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5964   -4.4260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  1  2  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  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2165447

   3-[[(2S)-azetidin-2-yl]methoxy]-5-(phenoxymethyl)-1,2-oxazole

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: 260.29

Molecular Weight (Monoisotopic): 260.1161

AlogP: 1.99

#Rotatable Bonds: 6

Polar Surface Area: 56.52

Molecular Species: BASE

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.64

CX LogP: 1.85

CX LogD: -0.36

Aromatic Rings: 2

Heavy Atoms: 19

QED Weighted: 0.86

Np Likeness Score: -0.96

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]

2. Yu LF, Zhang HK, Gunosewoyo H, Kozikowski AP..  (2012)  From α4β2 Nicotinic Ligands to the Discovery of σ1 Receptor Ligands: Pharmacophore Analysis and Rational Design.,  3  (12): [PMID:23641311] [10.1021/ml3002715]

Source

Source(1):

• Scientific Literature