5-(4-fluorophenyl)-3-(3-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)phenyl)oxazolidin-2-one

ID: ALA4095615

PubChem CID: 137652904

Max Phase: Preclinical

Molecular Formula: C21H22FNO8

Molecular Weight: 435.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1OC(c2ccc(F)cc2)CN1c1cccc(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)c1

Standard InChI:  InChI=1S/C21H22FNO8/c22-12-6-4-11(5-7-12)15-9-23(21(28)31-15)13-2-1-3-14(8-13)29-20-19(27)18(26)17(25)16(10-24)30-20/h1-8,15-20,24-27H,9-10H2/t15?,16-,17-,18+,19-,20-/m1/s1

Standard InChI Key:  ZKYYBLDNDWMVMH-FJVJWUHISA-N

Molfile:  

     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
   13.7788   -1.9737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4808   -0.4923    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1154   -0.3597    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0444   -1.7069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0625   -2.5820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1318   -2.9771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5915   -1.9076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9425   -1.1669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7645   -1.1005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2261   -1.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8752   -2.5157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3424   -3.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7714   -4.8247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3116   -6.0687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9924   -5.6166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9556   -4.7940    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.6736   -5.5600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8865   -5.7800    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5044   -4.1185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8685   -3.3856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4161   -2.7060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5997   -2.7580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2378   -3.4954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6923   -4.1720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7563   -5.9022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8903   -6.7094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6550   -6.9954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2863   -6.4751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1479   -5.6655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3832   -5.3832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0523   -6.7600    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  6 12  1  0
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  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  1
  7  1  1  1
  8  2  1  6
  9  3  1  1
 10  4  1  6
 14 15  1  0
 15 13  1  0
 13 16  1  0
 16 17  1  0
 17 14  1  0
 17 18  2  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
 16 19  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 25  1  0
 15 25  1  0
 28 31  1  0
 21  1  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4095615

   ---

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: 435.40

Molecular Weight (Monoisotopic): 435.1329

AlogP: 0.70

#Rotatable Bonds: 5

Polar Surface Area: 128.92

Molecular Species: NEUTRAL

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.20

CX Basic pKa: ┄

CX LogP: 0.88

CX LogD: 0.88

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.54

Np Likeness Score: 0.37

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