Benzyl (S)-4-methyl-1-oxo-1-((S)-1-oxo-3-((S)-2-oxopyrrolidin-3-yl)propan-2-ylamino)pentan-2-ylcarbamate

ID: ALA4850298

PubChem CID: 141697527

Max Phase: Preclinical

Molecular Formula: C21H29N3O5

Molecular Weight: 403.48

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)C[C@H](NC(=O)OCc1ccccc1)C(=O)N[C@H](C=O)C[C@@H]1CCNC1=O

Standard InChI:  InChI=1S/C21H29N3O5/c1-14(2)10-18(24-21(28)29-13-15-6-4-3-5-7-15)20(27)23-17(12-25)11-16-8-9-22-19(16)26/h3-7,12,14,16-18H,8-11,13H2,1-2H3,(H,22,26)(H,23,27)(H,24,28)/t16-,17-,18-/m0/s1

Standard InChI Key:  QYENXTYKACLCGO-BZSNNMDCSA-N

Molfile:  

 
     RDKit          2D

 29 30  0  0  0  0  0  0  0  0999 V2000
   35.9900  -20.7829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8150  -20.7829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0687  -19.9980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4046  -19.5114    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.7364  -19.9980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7071  -22.4504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4206  -22.0333    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.1372  -22.4451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1403  -23.2701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8548  -22.0278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8569  -23.6778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8599  -24.5029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5662  -23.2648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5631  -22.4398    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.8476  -21.2028    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.2766  -22.0225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9932  -22.4344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9963  -23.2595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.2735  -21.1975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9516  -19.7403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.9906  -22.0386    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.7102  -23.2755    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.2771  -22.4559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5605  -22.0439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5612  -21.2186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8454  -20.8109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1351  -21.2240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1408  -22.0533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8530  -22.4615    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
  4  5  1  0
  5  1  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  6
  8 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  1  0
 10 14  1  0
 10 15  2  0
 16 14  1  1
 16 17  1  0
 17 18  2  0
 16 19  1  0
  1 19  1  1
  5 20  2  0
  6 21  1  0
  6 22  2  0
 21 23  1  0
 23 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
M  END

Alternative Forms

1. Parent:

   

   ALA4850298

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 403.48

Molecular Weight (Monoisotopic): 403.2107

AlogP: 1.54

#Rotatable Bonds: 10

Polar Surface Area: 113.60

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.68

CX Basic pKa: ┄

CX LogP: 1.28

CX LogD: 1.28

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.51

Np Likeness Score: 0.37

References

1. Vankadara S, Wong YX, Liu B, See YY, Tan LH, Tan QW, Wang G, Karuna R, Guo X, Tan ST, Fong JY, Joy J, Chia CSB..  (2021)  A head-to-head comparison of the inhibitory activities of 15 peptidomimetic SARS-CoV-2 3CLpro inhibitors.,  48  [PMID:34271072] [10.1016/j.bmcl.2021.128263]

2. Vuong W, Fischer C, Khan MB, van Belkum MJ, Lamer T, Willoughby KD, Lu J, Arutyunova E, Joyce MA, Saffran HA, Shields JA, Young HS, Nieman JA, Tyrrell DL, Lemieux MJ, Vederas JC..  (2021)  Improved SARS-CoV-2 M^pro inhibitors based on feline antiviral drug GC376: Structural enhancements, increased solubility, and micellar studies.,  222  [PMID:34118724] [10.1016/j.ejmech.2021.113584]

3. La Monica G, Bono A, Lauria A, Martorana A..  (2022)  Targeting SARS-CoV-2 Main Protease for Treatment of COVID-19: Covalent Inhibitors Structure-Activity Relationship Insights and Evolution Perspectives.,  65  (19.0): [PMID:36169610] [10.1021/acs.jmedchem.2c01005]

4. Gao K, Wang R, Chen J, Tepe JJ, Huang F, Wei GW..  (2021)  Perspectives on SARS-CoV-2 Main Protease Inhibitors.,  64  (23.0): [PMID:34798775] [10.1021/acs.jmedchem.1c00409]

5. Chen R, Gao Y, Liu H, Li H, Chen W, Ma J..  (2023)  Advances in research on 3C-like protease (3CL^pro) inhibitors against SARS-CoV-2 since 2020.,  14  (1): [PMID:36760740] [10.1039/d2md00344a]

Source

Source(1):

• Scientific Literature