rac-3-(3-Chlorophenyl)-5-(4-fluorophenyl)-1,3-oxazolidin-2-one

ID: ALA4104260

PubChem CID: 137657222

Max Phase: Preclinical

Molecular Formula: C15H11ClFNO2

Molecular Weight: 291.71

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1OC(c2ccc(F)cc2)CN1c1cccc(Cl)c1

Standard InChI:  InChI=1S/C15H11ClFNO2/c16-11-2-1-3-13(8-11)18-9-14(20-15(18)19)10-4-6-12(17)7-5-10/h1-8,14H,9H2

Standard InChI Key:  WCEVDLJTVKJBSG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 20 22  0  0  0  0  0  0  0  0999 V2000
   22.7518  -19.9651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.4326  -19.5130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2148  -18.7252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3958  -18.6904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.1138  -19.4564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3267  -19.6764    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.9446  -18.0149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3087  -17.2820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8563  -16.6024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0398  -16.6544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6779  -17.3918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1325  -18.0684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1964  -19.7986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3305  -20.6058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0952  -20.8918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7265  -20.3715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5881  -19.5618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8234  -19.2796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4925  -20.6564    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   22.2190  -15.8701    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  1  1  0
  5  6  2  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  7  1  0
  4  7  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
  2 13  1  0
 16 19  1  0
  9 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4104260

   ---

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: 291.71

Molecular Weight (Monoisotopic): 291.0462

AlogP: 4.18

#Rotatable Bonds: 2

Polar Surface Area: 29.54

Molecular Species: NEUTRAL

HBA: 2

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.05

CX LogD: 4.05

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.83

Np Likeness Score: -1.38

References

1. Fujimoto J, Okamoto R, Noguchi N, Hara R, Masada S, Kawamoto T, Nagase H, Tamura YO, Imanishi M, Takagahara S, Kubo K, Tohyama K, Iida K, Andou T, Miyahisa I, Matsui J, Hayashi R, Maekawa T, Matsunaga N..  (2017)  Discovery of 3,5-Diphenyl-4-methyl-1,3-oxazolidin-2-ones as Novel, Potent, and Orally Available Δ-5 Desaturase (D5D) Inhibitors.,  60  (21): [PMID:29023121] [10.1021/acs.jmedchem.7b01210]

Source

Source(1):

• Scientific Literature