(2S)-2-[5-(3-chlorobenzyl)-2-oxooxazolidin-3-yl]-4-methyl-N-[(S)-1-oxo-3-{(S)-2-oxopyrrolidin-3-yl}propan-2-yl]pentanamide

ID: ALA4173836

PubChem CID: 145952521

Max Phase: Preclinical

Molecular Formula: C23H30ClN3O5

Molecular Weight: 463.96

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C23H30ClN3O5/c1-14(2)8-20(22(30)26-18(13-28)11-16-6-7-25-21(16)29)27-12-19(32-23(27)31)10-15-4-3-5-17(24)9-15/h3-5,9,13-14,16,18-20H,6-8,10-12H2,1-2H3,(H,25,29)(H,26,30)/t16-,18-,19?,20-/m0/s1

Standard InChI Key:  HPMLVVHQNDVVJA-ZXBFEJPJSA-N

Molfile:  

     RDKit          2D

 32 34  0  0  0  0  0  0  0  0999 V2000
    6.8667   -4.1083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5812   -3.6959    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1523   -3.6959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8667   -4.9333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2957   -4.1083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0101   -3.6959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2957   -4.9333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7246   -4.1083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0101   -5.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4378   -4.1083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6825   -3.7771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1304   -4.3902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5430   -5.1048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3499   -4.9331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1007   -6.1639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9077   -6.3354    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.3203   -5.6209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7681   -5.0079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2075   -5.8585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4892   -6.7176    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3870   -5.9447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9050   -5.2776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0853   -5.3635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7490   -6.1178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2386   -6.7871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0567   -6.6978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1523   -2.8709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8667   -2.4584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8667   -1.6334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5812   -2.8709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5087   -2.9706    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6006   -4.6959    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  1  0
  1  4  2  0
  2  5  1  0
  5  6  1  6
  5  7  1  0
  6  8  2  0
  9  7  1  6
  3 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 10  1  0
  9 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
  9 18  1  0
 13 19  1  0
 15 20  2  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
  3 27  1  1
 27 28  1  0
 28 29  1  0
 28 30  1  0
 11 31  2  0
 23 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4173836

   ---

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: 463.96

Molecular Weight (Monoisotopic): 463.1874

AlogP: 2.33

#Rotatable Bonds: 10

Polar Surface Area: 104.81

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.54

CX Basic pKa: ┄

CX LogP: 2.28

CX LogD: 2.28

Aromatic Rings: 1

Heavy Atoms: 32

QED Weighted: 0.52

Np Likeness Score: 0.07

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