Sodium (2S)-2-{(2S)-2-[5-(3-chlorobenzyl)-2-oxooxazolidin-3-yl]-4-methylpentanamido}-1-hydroxy-3-[(S)-2-oxopyrrolidin-3-yl]propane-1-sulfonate

ID: ALA4166569

PubChem CID: 145954027

Max Phase: Preclinical

Molecular Formula: C23H31ClN3NaO8S

Molecular Weight: 546.04

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)C[C@@H](C(=O)N[C@@H](C[C@@H]1CCNC1=O)C(O)S(=O)(=O)[O-])N1CC(Cc2cccc(Cl)c2)OC1=O.[Na+]

Standard InChI:  InChI=1S/C23H32ClN3O8S.Na/c1-13(2)8-19(27-12-17(35-23(27)31)10-14-4-3-5-16(24)9-14)21(29)26-18(22(30)36(32,33)34)11-15-6-7-25-20(15)28;/h3-5,9,13,15,17-19,22,30H,6-8,10-12H2,1-2H3,(H,25,28)(H,26,29)(H,32,33,34);/q;+1/p-1/t15-,17?,18-,19-,22?;/m0./s1

Standard InChI Key:  IDFSZOBFENHNGI-CWEIXUFESA-M

Molfile:  

     RDKit          2D

 37 38  0  0  0  0  0  0  0  0999 V2000
   19.9418   -1.5584    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
   20.8334   -2.2459    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.4252   -2.9626    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   21.2500   -2.9578    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.2835   -4.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9979   -3.7917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.5690   -3.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2835   -5.0292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7124   -4.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4269   -3.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7124   -5.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4269   -5.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8545   -4.2042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.0992   -3.8730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5472   -4.4861    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.9598   -5.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7666   -5.0289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5174   -6.2598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3245   -6.4313    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.7370   -5.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1848   -5.1037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6242   -5.9543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9059   -6.8135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8037   -6.0406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3217   -5.3734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5020   -5.4593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1657   -6.2137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6553   -6.8829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4734   -6.7936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5690   -2.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2835   -2.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2835   -1.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9979   -2.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9254   -3.0664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.1413   -4.2042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7098   -2.5516    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0173   -4.7917    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0
  4  3  2  0
  5  6  1  0
  5  7  1  0
  5  8  2  0
  9  6  1  6
  9 10  1  0
  9 11  1  0
 12 11  1  6
  7 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 13  1  0
 12 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 12 21  1  0
 16 22  1  0
 18 23  2  0
 22 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 24  1  0
  7 30  1  1
 30 31  1  0
 31 32  1  0
 31 33  1  0
 14 34  2  0
 10 35  1  0
 10  3  1  0
  3 36  1  0
 26 37  1  0
M  CHG  2   1   1  36  -1
M  END

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: 546.04

Molecular Weight (Monoisotopic): 545.1599

AlogP: 1.34

#Rotatable Bonds: 11

Polar Surface Area: 162.34

Molecular Species: ACID

HBA: 7

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: -0.86

CX Basic pKa: ┄

CX LogP: 0.48

CX LogD: -0.84

Aromatic Rings: 1

Heavy Atoms: 36

QED Weighted: 0.30

Np Likeness Score: -0.01

References

1. Damalanka VC, Kim Y, Galasiti Kankanamalage AC, Rathnayake AD, Mehzabeen N, Battaile KP, Lovell S, Nguyen HN, Lushington GH, Chang KO, Groutas WC..  (2018)  Structure-guided design, synthesis and evaluation of oxazolidinone-based inhibitors of norovirus 3CL protease.,  143  [PMID:29227928] [10.1016/j.ejmech.2017.12.014]

2. Damalanka VC, Kim Y, Galasiti Kankanamalage AC, Rathnayake AD, Mehzabeen N, Battaile KP, Lovell S, Nguyen HN, Lushington GH, Chang KO, Groutas WC..  (2018)  Structure-guided design, synthesis and evaluation of oxazolidinone-based inhibitors of norovirus 3CL protease.,  143  [PMID:29227928] [10.1016/j.ejmech.2017.12.014]

Source

Source(1):

• Scientific Literature