4-((2-oxo-3-phenyloxazolidin-5-yl)methoxy)benzamide

ID: ALA1097398

PubChem CID: 46887463

Max Phase: Preclinical

Molecular Formula: C17H16N2O4

Molecular Weight: 312.33

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C17H16N2O4/c18-16(20)12-6-8-14(9-7-12)22-11-15-10-19(17(21)23-15)13-4-2-1-3-5-13/h1-9,15H,10-11H2,(H2,18,20)

Standard InChI Key:  ZWXFCUZKPFDPGP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   15.3041  -17.1787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1291  -17.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3859  -16.3951    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.7166  -15.9083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0516  -16.3951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8938  -17.8945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0688  -17.8970    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6585  -18.6128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7154  -15.0833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0952  -15.9781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8118  -16.3891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5239  -15.9741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5206  -15.1482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7993  -14.7391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0901  -15.1565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8328  -18.6124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4225  -19.3273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8373  -20.0414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6666  -20.0362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0730  -19.3207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4280  -20.7577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6030  -20.7614    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.8436  -21.4704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 11 12  1  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  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1097398

   4-((2-Oxo-3-phenyloxazolidin-5-yl)methoxy)benzamide

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: 312.33

Molecular Weight (Monoisotopic): 312.1110

AlogP: 2.19

#Rotatable Bonds: 5

Polar Surface Area: 81.86

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.08

CX LogD: 2.08

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.92

Np Likeness Score: -0.97

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