sodium-(5S,8S)-5-Isobutyl-3,6,11-trioxo-8-(((S)-2-oxopyrrolidin-3-yl)-methyl)-1-phenyl-2,10-dioxa-4,7-diazahexadecane-9-sulfonate

ID: ALA4068460

PubChem CID: 137631811

Max Phase: Preclinical

Molecular Formula: C27H40N3NaO9S

Molecular Weight: 583.70

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCC(=O)OC([C@H](C[C@@H]1CCNC1=O)NC(=O)[C@H](CC(C)C)NC(=O)OCc1ccccc1)S(=O)(=O)[O-].[Na+]

Standard InChI:  InChI=1S/C27H41N3O9S.Na/c1-4-5-7-12-23(31)39-26(40(35,36)37)22(16-20-13-14-28-24(20)32)29-25(33)21(15-18(2)3)30-27(34)38-17-19-10-8-6-9-11-19;/h6,8-11,18,20-22,26H,4-5,7,12-17H2,1-3H3,(H,28,32)(H,29,33)(H,30,34)(H,35,36,37);/q;+1/p-1/t20-,21-,22-,26?;/m0./s1

Standard InChI Key:  LLFRIYQRGIGTCQ-AZWYUVBXSA-M

Molfile:  

     RDKit          2D

 42 42  0  0  0  0  0  0  0  0999 V2000
   21.1855  -10.3904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.7766   -9.6761    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   20.3653  -10.3865    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2093   -9.7096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2076  -10.5391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9212  -10.9507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6373  -10.5384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6371   -9.7082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9226   -9.2983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3478   -9.2933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0633   -9.7001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7781   -9.2852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4916   -9.6994    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.7735   -8.4634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1998   -9.2762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9151   -9.6872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   17.9099   -8.0354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9053   -7.2135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6253   -8.4463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9198  -10.5090    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6328   -9.2803    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.3522   -9.6842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0670   -9.2693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3568  -10.5102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0723  -10.9212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1631  -11.7356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9730  -11.9156    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.3780  -11.1915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8275  -10.5807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5529  -12.2909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0624   -8.4475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.7772   -8.0326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7725   -7.2066    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.4973   -9.2653    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.4927   -8.4435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2828  -11.1604    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   22.2035   -8.0311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9162   -8.4404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6269   -8.0280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3395   -8.4373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5730   -9.5853    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 13 15  1  0
 15 16  1  0
 15 17  1  1
 17 18  1  0
 18 19  1  0
 18 20  1  0
 16 21  2  0
 16 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  6
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 26 30  1  0
 27 31  2  0
 24  2  1  0
 24 32  1  0
 32 33  1  0
 33 34  2  0
  2 35  1  0
 33 36  1  0
 26 37  1  1
 36 38  1  0
 38 39  1  0
 39 40  1  0
 40 41  1  0
M  CHG  2  35  -1  42   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: 583.70

Molecular Weight (Monoisotopic): 583.2564

AlogP: 2.68

#Rotatable Bonds: 16

Polar Surface Area: 177.20

Molecular Species: ACID

HBA: 8

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: -0.78

CX Basic pKa: ┄

CX LogP: 2.05

CX LogD: 0.63

Aromatic Rings: 1

Heavy Atoms: 40

QED Weighted: 0.13

Np Likeness Score: 0.28

References

1. Galasiti Kankanamalage AC, Kim Y, Rathnayake AD, Alliston KR, Butler MM, Cardinale SC, Bowlin TL, Groutas WC, Chang KO..  (2017)  Design, Synthesis, and Evaluation of Novel Prodrugs of Transition State Inhibitors of Norovirus 3CL Protease.,  60  (14): [PMID:28671827] [10.1021/acs.jmedchem.7b00497]

Source

Source(1):

• Scientific Literature