5-[(2(S)-Azetidinyl)methoxy]-3-isoxazolylmethanol

ID: ALA2165451

PubChem CID: 56949768

Max Phase: Preclinical

Molecular Formula: C8H12N2O3

Molecular Weight: 184.19

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C8H12N2O3/c11-4-7-3-8(13-10-7)12-5-6-1-2-9-6/h3,6,9,11H,1-2,4-5H2/t6-/m0/s1

Standard InChI Key:  RWITUAISEGLCND-LURJTMIESA-N

Molfile:  

     RDKit          2D

 13 14  0  0  0  0  0  0  0  0999 V2000
    4.1874  -17.3748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0124  -17.3748    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2692  -16.5907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5999  -16.1039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9349  -16.5907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9791  -16.1706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2166  -16.1748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5016  -16.5864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7877  -16.1730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5705  -15.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7734  -15.5875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9859  -16.3848    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6979  -16.5755    0.0000 O   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:

   

   ALA2165451

   [5-[[(2S)-azetidin-2-yl]methoxy]-1,2-oxazol-3-yl]methanol

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: 184.19

Molecular Weight (Monoisotopic): 184.0848

AlogP: -0.09

#Rotatable Bonds: 4

Polar Surface Area: 67.52

Molecular Species: BASE

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.61

CX Basic pKa: 9.61

CX LogP: -0.83

CX LogD: -3.01

Aromatic Rings: 1

Heavy Atoms: 13

QED Weighted: 0.68

Np Likeness Score: 0.13

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