sodium-(5S,8S)-5-(Cyclohexylmethyl)-13-methyl-3,6,11,14-tetraoxo-8-(((S)-2-oxopyrrolidin-3-yl)methyl)-1-phenyl-2,10,15-trioxa-4,7,12-triazahexadecane-9-sulfonate

ID: ALA4088437

PubChem CID: 137642745

Max Phase: Preclinical

Molecular Formula: C29H41N4NaO11S

Molecular Weight: 654.74

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)C(C)NC(=O)OC([C@H](C[C@@H]1CCNC1=O)NC(=O)[C@H](CC1CCCCC1)NC(=O)OCc1ccccc1)S(=O)(=O)[O-].[Na+]

Standard InChI:  InChI=1S/C29H42N4O11S.Na/c1-18(26(36)42-2)31-29(38)44-27(45(39,40)41)23(16-21-13-14-30-24(21)34)32-25(35)22(15-19-9-5-3-6-10-19)33-28(37)43-17-20-11-7-4-8-12-20;/h4,7-8,11-12,18-19,21-23,27H,3,5-6,9-10,13-17H2,1-2H3,(H,30,34)(H,31,38)(H,32,35)(H,33,37)(H,39,40,41);/q;+1/p-1/t18?,21-,22-,23-,27?;/m0./s1

Standard InChI Key:  HKKKLIZQJRUUCW-XRIGPHBZSA-M

Molfile:  

     RDKit          2D

 47 48  0  0  0  0  0  0  0  0999 V2000
   22.3182  -14.5437    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
   21.0184  -15.2566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6098  -14.5424    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   20.1984  -15.2526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0296  -14.5736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0279  -15.4029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7413  -15.8142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4571  -15.4022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4570  -14.5723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7427  -14.1624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1675  -14.1574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8828  -14.5641    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5974  -14.1493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3193  -14.5609    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.5927  -13.3277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0329  -14.1443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7482  -14.5551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0282  -13.3185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7430  -12.9036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7529  -15.3766    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.4655  -14.1387    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.1856  -14.5506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9002  -14.1357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1902  -15.3762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9055  -15.7872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9963  -16.6015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8041  -16.7727    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.2108  -16.0573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6606  -15.4467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3863  -17.1565    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8955  -13.3142    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6103  -12.8992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6056  -12.0735    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.3301  -14.1317    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.3255  -13.3101    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1162  -16.0263    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   21.3147  -11.6587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0286  -12.0655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7377  -11.6506    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.4516  -12.0573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0332  -12.8870    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.3100  -10.8371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4621  -13.3203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1747  -12.9090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1770  -12.0823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4606  -11.6684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7418  -12.0815    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
 33 37  1  0
 37 38  1  0
 38 39  1  0
 39 40  1  0
 38 41  2  0
 37 42  1  0
 19 43  1  0
 19 47  1  0
 43 44  1  0
 44 45  1  0
 45 46  1  0
 46 47  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: 654.74

Molecular Weight (Monoisotopic): 654.2571

AlogP: 1.76

#Rotatable Bonds: 14

Polar Surface Area: 215.53

Molecular Species: ACID

HBA: 10

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 15

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: -1.13

CX Basic pKa: ┄

CX LogP: 0.78

CX LogD: -0.45

Aromatic Rings: 1

Heavy Atoms: 45

QED Weighted: 0.11

Np Likeness Score: 0.11

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