(1R,2S,5S)-N-((S)-4-amino-1-cyclobutyl-3,4-dioxobutan-2-yl)-3-((S)-2-(3-tert-butylureido)-3,3-dimethylbutanoyl)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxamide

ID: ALA1233448

Cas Number: 569677-40-3

PubChem CID: 10324368

Max Phase: Preclinical

Molecular Formula: C27H45N5O5

Molecular Weight: 519.69

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(C)NC(=O)N[C@H](C(=O)N1C[C@H]2[C@@H]([C@H]1C(=O)N[C@@H](CC1CCC1)C(=O)C(N)=O)C2(C)C)C(C)(C)C

Standard InChI:  InChI=1S/C27H45N5O5/c1-25(2,3)20(30-24(37)31-26(4,5)6)23(36)32-13-15-17(27(15,7)8)18(32)22(35)29-16(19(33)21(28)34)12-14-10-9-11-14/h14-18,20H,9-13H2,1-8H3,(H2,28,34)(H,29,35)(H2,30,31,37)/t15-,16-,17-,18-,20+/m0/s1

Standard InChI Key:  LHHCSNFAOIFYRV-ZYNAIFEFSA-N

Molfile:  

     RDKit          2D

 39 41  0  0  0  0  0  0  0  0999 V2000
   11.0366   -2.8245    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8946   -6.7453    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3363   -6.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5123   -6.7885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8946   -5.9204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6277   -1.9854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0381   -7.1579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7526   -5.9204    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2965   -5.9246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5612   -4.1601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4657   -6.7453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5499   -3.3352    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3157   -7.5662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1323   -4.1796    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7512   -5.5079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4657   -5.9204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1575   -2.9995    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.8628   -5.4076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4527   -1.9874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4235   -4.6018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4347   -5.4267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4737   -5.9621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1802   -5.5079    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.0381   -4.6829    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6091   -7.1579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7035   -4.1990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0381   -5.5079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2924   -5.3878    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0384   -2.7009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6241   -3.4143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8524   -4.5823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7490   -6.3287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6091   -5.5079    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.9899   -4.1406    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.3236   -5.9204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4491   -3.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2812   -4.5628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3236   -6.7453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3693   -4.1989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 35 27  1  0
 16 32  1  0
  4  3  1  0
 20 21  2  0
 26 20  1  1
 26 36  1  0
  9 22  1  0
 19 29  1  0
 18 22  1  0
 20 14  1  0
  5 33  1  0
 37 34  1  0
 30 29  1  0
 39 24  1  0
 23  5  1  0
 10 37  1  0
 16 23  1  0
 37 28  2  0
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  5  2  2  0
 24 26  1  0
 29  6  1  0
 14 31  1  0
 10 12  2  0
 31 10  1  0
 38 25  1  0
 36 30  1  0
 31 18  1  6
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 16 15  1  0
 27  8  2  0
 29 36  1  0
 30 39  1  0
 33 35  1  0
 35 38  1  6
 36 17  1  1
 30  1  1  1
 38 13  1  0
  3  9  1  0
 22  4  1  0
 27 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1233448

   (1r,2s,5s)-N-[(1s)-3-Amino-1-(Cyclobutylmethyl)-2,3-Dioxopropyl]-3-[(2s)-2-{[(Tert-Butylamino)carbonyl]amino}-3,3-Dimethylbutanoyl]-6,6-Dimethyl-3-Azabicyclo[3.1.0]hexane-2-Carboxamide

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: 519.69

Molecular Weight (Monoisotopic): 519.3421

AlogP: 1.71

#Rotatable Bonds: 8

Polar Surface Area: 150.70

Molecular Species: NEUTRAL

HBA: 5

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.44

CX Basic pKa: ┄

CX LogP: 1.78

CX LogD: 1.78

Aromatic Rings: ┄

Heavy Atoms: 37

QED Weighted: 0.36

Np Likeness Score: 0.23

References

1. Ghosal A, Yuan Y, Tong W, Su AD, Gu C, Chowdhury SK, Kishnani NS, Alton KB..  (2011)  Characterization of human liver enzymes involved in the biotransformation of boceprevir, a hepatitis C virus protease inhibitor.,  39  (3): [PMID:21123164] [10.1124/dmd.110.036996]

2. Ghosal A, Yuan Y, Tong W, Su AD, Gu C, Chowdhury SK, Kishnani NS, Alton KB..  (2011)  Characterization of human liver enzymes involved in the biotransformation of boceprevir, a hepatitis C virus protease inhibitor.,  39  (3): [PMID:21123164] [10.1124/dmd.110.036996]

3. Bernhard Ellinger, Denisa Bojkova, Andrea Zaliani, Jindrich Cinatl, Carsten Claussen, Sandra Westhaus, Jeanette Reinshagen, Maria Kuzikov, Markus Wolf, Gerd Geisslinger, Philip Gribbon, Sandra Ciesek.  (2020)  Identification of inhibitors of SARS-CoV-2 in-vitro cellular toxicity in human (Caco-2) cells using a large scale drug repurposing collection,  [10.21203/rs.3.rs-23951/v1]

4. Maria Kuzikov, Elisa Costanzi, Jeanette Reinshagen, Francesca Esposito, Laura Vangeel, Markus Wolf, Bernhard Ellinger, Carsten Claussen, Gerd Geisslinger, Angela Corona, Daniela Iaconis, Carmine Talarico, Candida Manelfi, Rolando Cannalire, Giulia Rossetti, Jonas Gossen, Simone Albani, Francesco Musiani, Katja Herzog, Yang Ye, Barbara Giabbai, Nicola Demitri, Dirk Jochmans, Steven De Jonghe, Jasper Rymenants, Vincenzo Summa, Enzo Tramontano, Andrea R. Beccari, Pieter Leyssen, Paola Storici, Johan Neyts, Philip Gribbon, and Andrea Zaliani.  (2020)  Identification of inhibitors of SARS-Cov2 M-Pro enzymatic activity using a small molecule repurposing screen,  [10.6019/CHEMBL4495564]

5. Andrea Zaliani, Laura Vangeel, Jeanette Reinshagen, Daniela Iaconis, Maria Kuzikov, Oliver Keminer, Markus Wolf, Bernhard Ellinger, Francesca Esposito, Angela Corona, Enzo Tramontano, Candida Manelfi, Katja Herzog, Dirk Jochmans, Steven De Jonghe, Winston Chiu, Thibault Francken, Joost Schepers, Caroline Collard, Kayvan Abbasi, Carsten Claussen , Vincenzo Summa, Andrea R. Beccari, Johan Neyts, Philip Gribbon and Pieter Leyssen.  (2020)  Cytopathic SARS-Cov2 screening on VERO-E6 cells in a large repurposing effort,  [10.6019/CHEMBL4495565]

Source

Source(2):

• Scientific Literature
• SARS-CoV-2 Screening Data 2020-21