2-(6-bromo-2-(4-methoxyphenyl)-2'-oxospiro[chromane-4,5'-oxazolidin]-3'-yl)acetic acid

ID: ALA5289568

Max Phase: Preclinical

Molecular Formula: C20H18BrNO6

Molecular Weight: 448.27

Names and Identifiers

Canonical SMILES:  COc1ccc(C2CC3(CN(CC(=O)O)C(=O)O3)c3cc(Br)ccc3O2)cc1

Standard InChI:  InChI=1S/C20H18BrNO6/c1-26-14-5-2-12(3-6-14)17-9-20(11-22(10-18(23)24)19(25)28-20)15-8-13(21)4-7-16(15)27-17/h2-8,17H,9-11H2,1H3,(H,23,24)

Standard InChI Key:  HQTKHUJWZXDFCW-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
    1.4286   -0.3189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7141    0.0935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3816    0.5784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1266    1.3630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3017    1.3630    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0467    0.5784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0002   -0.3189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0002   -1.1438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7141   -1.5563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4286   -1.1438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1431   -1.5563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8575   -1.1438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8575   -0.3189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1431    0.0935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5392    2.0777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1108    2.0777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9360    2.0777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3486    2.7924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3486    1.3630    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5721    0.0937    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -0.7148   -1.5564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7150   -2.3817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4280   -2.7924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1428   -2.3796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1444   -1.5585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4326   -1.1420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8575   -2.7922    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5721   -2.3796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  5  4  1  0
  6  5  1  0
  2  6  1  0
  2  7  1  0
  7  8  1  0
  8  9  1  0
  1 10  1  0
 10  9  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 14  1  2  0
 13 14  1  0
  4 15  2  0
  5 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 13 20  1  0
 21  8  1  0
 22 21  2  0
 23 22  1  0
 24 23  2  0
 25 24  1  0
 26 25  2  0
 21 26  1  0
 24 27  1  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5289568

   ---

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: 448.27

Molecular Weight (Monoisotopic): 447.0317

AlogP: 3.71

#Rotatable Bonds: 4

Polar Surface Area: 85.30

Molecular Species: ACID

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.83

CX Basic pKa: ┄

CX LogP: 3.18

CX LogD: -0.31

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.77

Np Likeness Score: 0.31

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