3-Chlorophenethyl ((S)-3-cyclohexyl-1-oxo-1-(((S)-1-oxo-3-((S)-2-oxopyrrolidin-3-yl)propan-2-yl)amino)propan-2-yl)carbamate

ID: ALA4103451

PubChem CID: 137656755

Max Phase: Preclinical

Molecular Formula: C25H34ClN3O5

Molecular Weight: 492.02

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C[C@H](C[C@@H]1CCNC1=O)NC(=O)[C@H](CC1CCCCC1)NC(=O)OCCc1cccc(Cl)c1

Standard InChI:  InChI=1S/C25H34ClN3O5/c26-20-8-4-7-18(13-20)10-12-34-25(33)29-22(14-17-5-2-1-3-6-17)24(32)28-21(16-30)15-19-9-11-27-23(19)31/h4,7-8,13,16-17,19,21-22H,1-3,5-6,9-12,14-15H2,(H,27,31)(H,28,32)(H,29,33)/t19-,21-,22-/m0/s1

Standard InChI Key:  DIYFESMLIMIHAX-BVSLBCMMSA-N

Molfile:  

     RDKit          2D

 34 36  0  0  0  0  0  0  0  0999 V2000
    9.7511  -18.7529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0419  -18.3444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0419  -17.5190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7511  -19.5743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4601  -18.3443    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3287  -18.7531    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.8824  -18.3442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1692  -18.7528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1693  -19.5742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7733  -20.9721    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.9666  -20.8014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8825  -19.9868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6339  -19.6483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1860  -20.2588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3602  -21.3492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5957  -18.7527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7509  -17.1062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7509  -16.2849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4599  -15.8762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1691  -16.2848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1691  -17.1061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4601  -17.5189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6224  -18.3421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9133  -18.7484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6251  -17.5250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2070  -18.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4979  -18.7438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7916  -18.3329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7968  -17.5184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0913  -17.1076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3813  -17.5139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3812  -18.3354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0873  -18.7425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6736  -18.7441    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  1
  1  4  2  0
  1  5  1  0
  2  6  1  0
  8  7  1  6
  8  9  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 10 14  1  0
 11 15  2  0
 12  9  1  6
  7 16  2  0
  5  8  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 17 22  1  0
  3 17  1  0
  6 23  1  0
 23 24  1  0
 23 25  2  0
 24 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 28  1  0
 32 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4103451

   ---

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: 492.02

Molecular Weight (Monoisotopic): 491.2187

AlogP: 3.16

#Rotatable Bonds: 11

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: 12.74

CX Basic pKa: ┄

CX LogP: 3.04

CX LogD: 3.04

Aromatic Rings: 1

Heavy Atoms: 34

QED Weighted: 0.41

Np Likeness Score: 0.09

References

1. Galasiti Kankanamalage AC, Kim Y, Rathnayake AD, Damalanka VC, Weerawarna PM, Doyle ST, Alsoudi AF, Dissanayake DMP, Lushington GH, Mehzabeen N, Battaile KP, Lovell S, Chang KO, Groutas WC..  (2017)  Structure-based exploration and exploitation of the S4 subsite of norovirus 3CL protease in the design of potent and permeable inhibitors.,  126  [PMID:27914364] [10.1016/j.ejmech.2016.11.027]

Source

Source(1):

• Scientific Literature