sodium-(5S,8S)-1-(3-Chlorophenyl)-5-(cyclohexylmethyl)-12-methyl-3,6,11-trioxo-8-(((S)-2-oxopyrrolidin-3-yl)methyl)-2,10-dioxa-4,7-diazatridecane-9-sulfonate

ID: ALA4088757

PubChem CID: 137642098

Max Phase: Preclinical

Molecular Formula: C28H39ClN3NaO9S

Molecular Weight: 630.16

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)C(=O)OC([C@H](C[C@@H]1CCNC1=O)NC(=O)[C@H](CC1CCCCC1)NC(=O)OCc1cccc(Cl)c1)S(=O)(=O)[O-].[Na+]

Standard InChI:  InChI=1S/C28H40ClN3O9S.Na/c1-17(2)26(35)41-27(42(37,38)39)23(15-20-11-12-30-24(20)33)31-25(34)22(14-18-7-4-3-5-8-18)32-28(36)40-16-19-9-6-10-21(29)13-19;/h6,9-10,13,17-18,20,22-23,27H,3-5,7-8,11-12,14-16H2,1-2H3,(H,30,33)(H,31,34)(H,32,36)(H,37,38,39);/q;+1/p-1/t20-,22-,23-,27?;/m0./s1

Standard InChI Key:  WYWGNRSPQAVAKH-PYQRGXIDSA-M

Molfile:  

     RDKit          2D

 44 45  0  0  0  0  0  0  0  0999 V2000
   33.9615  -23.2884    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
   32.9800  -24.0942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.5715  -23.3804    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   32.1603  -24.0903    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.9944  -23.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9927  -24.2405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7058  -24.6518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4214  -24.2398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4212  -23.4102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7072  -23.0005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1316  -22.9955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8465  -23.4021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.5610  -22.9874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2845  -23.4075    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.5563  -22.1662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.9960  -22.9823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   29.7157  -24.2144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.4299  -22.9854    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.1478  -23.3885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8622  -22.9738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1525  -24.2140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8674  -24.6246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9582  -25.4386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7676  -25.6184    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.1723  -24.8948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6223  -24.2844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3484  -25.9935    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.8576  -22.1525    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.5720  -21.7378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5673  -20.9124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2916  -22.9699    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.2870  -22.1486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.0785  -24.8637    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   30.4207  -22.1564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1330  -21.7451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1354  -20.9187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4191  -20.5052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7006  -20.9180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7055  -25.4731    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   33.2763  -20.4977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8538  -20.5058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0
  4  3  2  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 14 16  1  0
 16 17  1  0
 16 18  1  1
 18 19  1  0
 17 20  2  0
 17 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  6
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 25 29  1  0
 26 30  2  0
 23  3  1  0
 23 31  1  0
 31 32  1  0
 32 33  1  0
  3 34  1  0
 32 35  2  0
 25 36  1  1
 19 37  1  0
 19 41  1  0
 37 38  1  0
 38 39  1  0
 39 40  1  0
 40 41  1  0
  7 42  1  0
 33 43  1  0
 33 44  1  0
M  CHG  2   1   1  34  -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: 630.16

Molecular Weight (Monoisotopic): 629.2174

AlogP: 3.33

#Rotatable Bonds: 13

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: -0.89

CX Basic pKa: ┄

CX LogP: 2.60

CX LogD: 1.32

Aromatic Rings: 1

Heavy Atoms: 42

QED Weighted: 0.19

Np Likeness Score: 0.03

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