1-(2,3-dihydrobenzo[b][1,4]dioxin-6-ylsulfonyl)-4-(4-methoxyphenylsulfonyl)piperazine

ID: ALA1088762

Cas Number: 562867-96-3

PubChem CID: 650361

Max Phase: Preclinical

Molecular Formula: C19H22N2O7S2

Molecular Weight: 454.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(S(=O)(=O)N2CCN(S(=O)(=O)c3ccc4c(c3)OCCO4)CC2)cc1

Standard InChI:  InChI=1S/C19H22N2O7S2/c1-26-15-2-4-16(5-3-15)29(22,23)20-8-10-21(11-9-20)30(24,25)17-6-7-18-19(14-17)28-13-12-27-18/h2-7,14H,8-13H2,1H3

Standard InChI Key:  HMGDKYUJSFVHIY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
   -4.6256    3.2179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6256    2.3929    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9112    1.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9112    1.1554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1967    0.7429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1967    2.3929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4822    1.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4822    1.1554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7678    0.7429    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1803    0.0284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3553    1.4574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0533    0.3304    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3388    0.7429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3757    0.3304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0533   -0.4946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3388   -0.9071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3757   -0.4946    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0901   -0.9071    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.5026   -0.1926    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6776   -1.6216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8046   -1.3196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5191   -0.9071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2335   -1.3196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9480   -0.9071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6625   -1.3196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6625   -2.1446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9480   -2.5571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2335   -2.1446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5191   -2.5571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8046   -2.1446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  0
  4  3  2  0
  6  3  1  0
  4  5  1  0
  5  8  2  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
 10  9  2  0
 12  9  1  0
 11  9  2  0
 15 12  1  0
 13 12  1  0
 13 14  1  0
 14 17  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 20 18  2  0
 19 18  2  0
 21 18  1  0
 30 21  2  0
 22 21  1  0
 22 23  2  0
 28 23  1  0
 23 24  1  0
 25 24  1  0
 26 25  1  0
 26 27  1  0
 28 27  1  0
 29 28  2  0
 30 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1088762

   1-(2,3-Dihydro-1,4-benzodioxin-6-ylsulfonyl)-4-[(4-methoxyphenyl)sulfonyl]piperazine

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: 454.53

Molecular Weight (Monoisotopic): 454.0868

AlogP: 1.16

#Rotatable Bonds: 5

Polar Surface Area: 102.45

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 1.07

CX LogD: 1.07

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.67

Np Likeness Score: -1.16

References

1. Boxer MB, Jiang JK, Vander Heiden MG, Shen M, Skoumbourdis AP, Southall N, Veith H, Leister W, Austin CP, Park HW, Inglese J, Cantley LC, Auld DS, Thomas CJ..  (2010)  Evaluation of substituted N,N'-diarylsulfonamides as activators of the tumor cell specific M2 isoform of pyruvate kinase.,  53  (3): [PMID:20017496] [10.1021/jm901577g]

2. PubChem BioAssay data set, 

3. PubChem BioAssay data set, 

4. PubChem BioAssay data set, 

5. PubChem BioAssay data set, 

6. 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]

7. 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(3):

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