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

ID: ALA2165443

PubChem CID: 56949921

Max Phase: Preclinical

Molecular Formula: C8H11FN2O2

Molecular Weight: 186.19

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  FCc1cc(OC[C@@H]2CCN2)on1

Standard InChI:  InChI=1S/C8H11FN2O2/c9-4-7-3-8(13-11-7)12-5-6-1-2-10-6/h3,6,10H,1-2,4-5H2/t6-/m0/s1

Standard InChI Key:  DTIFFHAURKBXJT-LURJTMIESA-N

Molfile:  

     RDKit          2D

 13 14  0  0  0  0  0  0  0  0999 V2000
   21.2128  -27.4505    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0379  -27.4505    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.2946  -26.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6254  -26.1796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9603  -26.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0045  -26.2463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2420  -26.2504    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.5271  -26.6620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8131  -26.2487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5958  -25.4507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7987  -25.6632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0112  -26.4604    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.7235  -26.6511    0.0000 F   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
M  END

Alternative Forms

1. Parent:

   

   ALA2165443

   5-[[(2S)-azetidin-2-yl]methoxy]-3-(fluoromethyl)-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: 186.19

Molecular Weight (Monoisotopic): 186.0805

AlogP: 0.88

#Rotatable Bonds: 4

Polar Surface Area: 47.29

Molecular Species: BASE

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.61

CX LogP: 0.06

CX LogD: -2.11

Aromatic Rings: 1

Heavy Atoms: 13

QED Weighted: 0.76

Np Likeness Score: -0.31

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