rac-3-(2,4-Dichloro-5-hydroxybenzyl)-5-phenyl-1,3-oxazolidin-2-one

ID: ALA4063561

PubChem CID: 137635527

Max Phase: Preclinical

Molecular Formula: C16H13Cl2NO3

Molecular Weight: 338.19

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1OC(c2ccccc2)CN1Cc1cc(O)c(Cl)cc1Cl

Standard InChI:  InChI=1S/C16H13Cl2NO3/c17-12-7-13(18)14(20)6-11(12)8-19-9-15(22-16(19)21)10-4-2-1-3-5-10/h1-7,15,20H,8-9H2

Standard InChI Key:  JRDMZVFOGVPJRO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
    7.5865  -20.8342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5852  -21.6616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3001  -22.0745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0166  -21.6612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0137  -20.8306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2983  -20.4214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8718  -20.4226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7853  -19.6022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9783  -19.4309    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5659  -20.1455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1182  -20.7584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7454  -20.2320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6425  -18.6772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8220  -18.5912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4903  -17.8376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6705  -17.7513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1849  -18.4194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5248  -19.1758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3435  -19.2585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9767  -17.1712    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.3643  -18.3344    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.0423  -19.8451    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11  7  1  0
  1  7  1  0
 10 12  2  0
  9 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 15 20  1  0
 17 21  1  0
 18 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4063561

   ---

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: 338.19

Molecular Weight (Monoisotopic): 337.0272

AlogP: 4.39

#Rotatable Bonds: 3

Polar Surface Area: 49.77

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.35

CX Basic pKa: ┄

CX LogP: 4.28

CX LogD: 3.95

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.90

Np Likeness Score: -0.14

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