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

ID: ALA2165442

PubChem CID: 56949919

Max Phase: Preclinical

Molecular Formula: C14H21N3O4

Molecular Weight: 295.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(NC1CCCC1)OCc1cc(OC[C@@H]2CCN2)on1

Standard InChI:  InChI=1S/C14H21N3O4/c18-14(16-10-3-1-2-4-10)20-9-12-7-13(21-17-12)19-8-11-5-6-15-11/h7,10-11,15H,1-6,8-9H2,(H,16,18)/t11-/m0/s1

Standard InChI Key:  UYZYLDHDYYFCFP-NSHDSACASA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
   13.0079  -26.2701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8329  -26.2701    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.0896  -25.4860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4204  -24.9993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7554  -25.4860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7995  -25.0659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0372  -25.0701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3221  -25.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6082  -25.0682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3910  -24.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5939  -24.4829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8064  -25.2800    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.5184  -25.4707    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5272  -26.2956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2461  -26.7004    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.8172  -26.7158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2549  -27.5254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5946  -28.0177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8579  -28.7995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6829  -28.7907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9293  -28.0033    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  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 17  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2165442

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

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: 295.34

Molecular Weight (Monoisotopic): 295.1532

AlogP: 1.58

#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: 13.96

CX Basic pKa: 9.61

CX LogP: 0.85

CX LogD: -1.32

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.83

Np Likeness Score: -0.78

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