Sodium (8S,11S)-8-(cyclohexylmethyl)-12-hydroxy-6,9-dioxo-11-(((S)-2-oxo-pyrrolidin-3-yl)methyl)-1-phenyl-2,5-dioxa-7,10-diazadodecane-12-sulfonate

ID: ALA4101004

PubChem CID: 137659845

Max Phase: Preclinical

Molecular Formula: C26H38N3NaO9S

Molecular Weight: 569.68

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(N[C@@H](CC1CCCCC1)C(=O)N[C@@H](C[C@@H]1CCNC1=O)C(O)S(=O)(=O)[O-])OCCOCc1ccccc1.[Na+]

Standard InChI:  InChI=1S/C26H39N3O9S.Na/c30-23-20(11-12-27-23)16-22(25(32)39(34,35)36)28-24(31)21(15-18-7-3-1-4-8-18)29-26(33)38-14-13-37-17-19-9-5-2-6-10-19;/h2,5-6,9-10,18,20-22,25,32H,1,3-4,7-8,11-17H2,(H,27,30)(H,28,31)(H,29,33)(H,34,35,36);/q;+1/p-1/t20-,21-,22-,25?;/m0./s1

Standard InChI Key:  GNBAPFQUNCJYFP-FLABFKKQSA-M

Molfile:  

     RDKit          2D

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   25.4073  -19.4685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   19.3935  -18.3334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6844  -18.7396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9781  -18.3287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   16.5682  -17.5092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8626  -17.0983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   26.9581  -17.1229    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
  2 17  1  0
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  4 15  1  0
  1 12  1  6
  9 23  1  0
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  6  3  1  0
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  1 27  1  0
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  7 25  1  0
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  9 10  1  0
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 23  8  2  0
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  3  7  1  0
  5  2  2  0
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 31 32  1  0
 32 33  1  0
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 34 35  1  0
 35 36  2  0
 36 37  1  0
 37 38  2  0
 38 39  1  0
 39 40  2  0
 40 35  1  0
M  CHG  2  17  -1  41   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: 569.68

Molecular Weight (Monoisotopic): 569.2407

AlogP: 1.49

#Rotatable Bonds: 14

Polar Surface Area: 180.36

Molecular Species: ACID

HBA: 8

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: -1.14

CX Basic pKa: ┄

CX LogP: 0.19

CX LogD: -1.02

Aromatic Rings: 1

Heavy Atoms: 39

QED Weighted: 0.16

Np Likeness Score: 0.06

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