5-[(4-tert-butylphenoxy)methyl]-3-phenyl-1,3-oxazolidin-2-one

ID: ALA1096713

PubChem CID: 46887372

Max Phase: Preclinical

Molecular Formula: C20H23NO3

Molecular Weight: 325.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(C)c1ccc(OCC2CN(c3ccccc3)C(=O)O2)cc1

Standard InChI:  InChI=1S/C20H23NO3/c1-20(2,3)15-9-11-17(12-10-15)23-14-18-13-21(19(22)24-18)16-7-5-4-6-8-16/h4-12,18H,13-14H2,1-3H3

Standard InChI Key:  AUWQGNKAKYHFEN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   15.6166  -23.3329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4416  -23.3334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6984  -22.5492    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.0291  -22.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3641  -22.5492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2063  -24.0487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3813  -24.0512    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9710  -24.7670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0279  -21.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4077  -22.1323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1243  -22.5433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8364  -22.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8331  -21.3024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1118  -20.8933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4026  -21.3107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1453  -24.7665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7350  -25.4814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1498  -26.1956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9791  -26.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3855  -25.4749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7405  -26.9119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9155  -26.9155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1561  -27.6245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3208  -27.6208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0
 12 13  2  0
 13 14  1  0
  6  7  1  0
 14 15  2  0
 15 10  1  0
  3 10  1  0
  2  3  1  0
  8 16  2  0
  7  8  1  0
 16 17  1  0
  3  4  1  0
 17 18  2  0
  4  9  2  0
 18 19  1  0
  4  5  1  0
 19 20  2  0
 20  8  1  0
  5  1  1  0
 18 21  1  0
 10 11  2  0
 21 22  1  0
  1  2  1  0
 21 23  1  0
 11 12  1  0
 21 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1096713

   5-[(4-Tert-butylphenoxy)methyl]-3-phenyl-1,3-oxazolidin-2-one

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: 325.41

Molecular Weight (Monoisotopic): 325.1678

AlogP: 4.39

#Rotatable Bonds: 4

Polar Surface Area: 38.77

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.77

CX LogD: 4.77

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.84

Np Likeness Score: -0.96

References

1. Brnardic EJ, Fraley ME, Garbaccio RM, Layton ME, Sanders JM, Culberson C, Jacobson MA, Magliaro BC, Hutson PH, O'Brien JA, Huszar SL, Uslaner JM, Fillgrove KL, Tang C, Kuo Y, Sur SM, Hartman GD..  (2010)  3-Aryl-5-phenoxymethyl-1,3-oxazolidin-2-ones as positive allosteric modulators of mGluR2 for the treatment of schizophrenia: Hit-to-lead efforts.,  20  (10): [PMID:20409708] [10.1016/j.bmcl.2010.03.089]

Source

Source(1):

• Scientific Literature