3-(Phenoxymethyl)-5-[(2(S)-pyrrolidinyl)methoxy]isoxazole

ID: ALA2165453

PubChem CID: 56949772

Max Phase: Preclinical

Molecular Formula: C15H18N2O3

Molecular Weight: 274.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  c1ccc(OCc2cc(OC[C@@H]3CCCN3)on2)cc1

Standard InChI:  InChI=1S/C15H18N2O3/c1-2-6-14(7-3-1)18-11-13-9-15(20-17-13)19-10-12-5-4-8-16-12/h1-3,6-7,9,12,16H,4-5,8,10-11H2/t12-/m0/s1

Standard InChI Key:  BYCCDPZWEJHAMN-LBPRGKRZSA-N

Molfile:  

     RDKit          2D

 20 22  0  0  0  0  0  0  0  0999 V2000
   20.1288  -16.9664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.9538  -16.9664    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.2106  -16.1823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5413  -15.6956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8763  -16.1823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9204  -15.7623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1580  -15.7664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.4431  -16.1780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7291  -15.7646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6393  -16.1671    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.6482  -16.9920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9350  -17.4077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9435  -18.2319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6629  -18.6375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3752  -18.2129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3632  -17.3901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6414  -14.9446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8346  -14.7721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4212  -15.4860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9725  -16.0997    0.0000 N   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
  6 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
  9 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20  9  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2165453

   3-(phenoxymethyl)-5-[[(2S)-pyrrolidin-2-yl]methoxy]-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: 274.32

Molecular Weight (Monoisotopic): 274.1317

AlogP: 2.38

#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: 10.28

CX LogP: 2.02

CX LogD: -0.71

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.88

Np Likeness Score: -0.69

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