2-(5-methyl-2-oxo-5-{2-[(3,4,5-trimethoxyphenyl)methoxy]phenyl}-1,3-oxazolidin-3-yl)acetic acid

ID: ALA5279118

Max Phase: Preclinical

Molecular Formula: C22H25NO8

Molecular Weight: 431.44

Names and Identifiers

Canonical SMILES:  COc1cc(COc2ccccc2C2(C)CN(CC(=O)O)C(=O)O2)cc(OC)c1OC

Standard InChI:  InChI=1S/C22H25NO8/c1-22(13-23(11-19(24)25)21(26)31-22)15-7-5-6-8-16(15)30-12-14-9-17(27-2)20(29-4)18(10-14)28-3/h5-10H,11-13H2,1-4H3,(H,24,25)

Standard InChI Key:  IOLZNHDJBITFKN-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    1.7867    0.2998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0723    0.7124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7397    1.1972    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4848    1.9817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6597    1.9817    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4049    1.1972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2472    2.6964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5777    2.6964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9903    3.4111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9903    1.9817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8974    2.6964    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3579    0.2998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7867   -0.5249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5012   -0.9374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2155   -0.5249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2155    0.2998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5012    0.7124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0723   -0.9374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3577   -0.5248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3567   -0.9374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3569   -1.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0698   -2.1732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7846   -1.7605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862   -0.9395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0744   -0.5230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5008   -0.5269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2155   -0.9395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4992   -2.1730    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4992   -2.9983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0698   -2.9984    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3550   -3.4111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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  3  4  1  0
  5  4  1  0
  6  5  1  0
  2  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  4 11  2  0
  2 12  1  0
  1 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 17  1  2  0
 16 17  1  0
 13 18  1  0
 18 19  1  0
 19 20  1  0
 21 20  2  0
 22 21  1  0
 23 22  2  0
 24 23  1  0
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 20 25  1  0
 24 26  1  0
 26 27  1  0
 23 28  1  0
 28 29  1  0
 22 30  1  0
 30 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5279118

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 431.44

Molecular Weight (Monoisotopic): 431.1580

AlogP: 3.04

#Rotatable Bonds: 9

Polar Surface Area: 103.76

Molecular Species: ACID

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.50

CX Basic pKa: ┄

CX LogP: 2.50

CX LogD: -0.87

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.65

Np Likeness Score: 0.17

References

1. Fernandes GFS, Scarim CB, Kim SH, Wu J, Castagnolo D..  (2023)  Oxazolidinones as versatile scaffolds in medicinal chemistry.,  14  (5): [PMID:37252095] [10.1039/d2md00415a]

Source

Source(1):

• Scientific Literature