5-((4-aminophenoxy)methyl)-3-phenyloxazolidin-2-one

ID: ALA1098335

PubChem CID: 18997192

Max Phase: Preclinical

Molecular Formula: C16H16N2O3

Molecular Weight: 284.32

Molecule Type: Small molecule

This compound is available for customization.

Associated Items:

Names and Identifiers

Canonical SMILES:  Nc1ccc(OCC2CN(c3ccccc3)C(=O)O2)cc1

Standard InChI:  InChI=1S/C16H16N2O3/c17-12-6-8-14(9-7-12)20-11-15-10-18(16(19)21-15)13-4-2-1-3-5-13/h1-9,15H,10-11,17H2

Standard InChI Key:  KBDYFHAVKBISDZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
   15.8416  -12.2454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6666  -12.2459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9234  -11.4617    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.2541  -10.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5891  -11.4617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4313  -12.9612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6063  -12.9637    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1960  -13.6795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2529  -10.1500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6327  -11.0448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3493  -11.4558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0614  -11.0408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0581  -10.2149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3368   -9.8058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6276  -10.2232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3703  -13.6790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9600  -14.3939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3748  -15.1081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2041  -15.1029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6105  -14.3874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9655  -15.8244    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 10 11  2  0
  1  2  1  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
M  END

Alternative Forms

Associated Targets(Human)

GRM2 Tchem Metabotropic glutamate receptor 2 (3206 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 284.32Molecular Weight (Monoisotopic): 284.1161AlogP: 2.67#Rotatable Bonds: 4
Polar Surface Area: 64.79Molecular Species: NEUTRALHBA: 4HBD: 1
#RO5 Violations: HBA (Lipinski): 5HBD (Lipinski): 2#RO5 Violations (Lipinski):
CX Acidic pKa: CX Basic pKa: 4.90CX LogP: 2.40CX LogD: 2.40
Aromatic Rings: 2Heavy Atoms: 21QED Weighted: 0.88Np Likeness Score: -0.76

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