(1,6-trimethyl ammonium)hexane; dibromide

ID: ALA332524

Cas Number: 55-97-0

PubChem CID: 5938

Product Number: H170991, Order Now?

Max Phase: Phase

Molecular Formula: C12H30Br2N2

Molecular Weight: 202.39

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Hexamethone bromide | Hexamethonium bromide | NSC-163965 | HEXAMETHONIUM BROMIDE|55-97-0|Simpatoblock|Hexamethonium dibromide|Gangliostat|Hexamethionium bromide|Bistrium bromide|Hexamethonium (Bromide)|Esametina|Hexameton|Vegolysen|Vegolysin|Hexonium dibromide|1,6-Hexanediaminium, N,N,N,N',N',N'-hexamethyl-, dibromide|Hexamethylenebis(trimethylammonium bromide)|HEXAMETHONE BROMIDE|Hexane-1,6-bis(trimethylammonium bromide)|Hexamethylenebis(trimethylammonium) bromide|8J77X3S603|NSC-163965|N1,N1,N1Show More⌵

Canonical SMILES:  C[N+](C)(C)CCCCCC[N+](C)(C)C.[Br-].[Br-]

Standard InChI:  InChI=1S/C12H30N2.2BrH/c1-13(2,3)11-9-7-8-10-12-14(4,5)6;;/h7-12H2,1-6H3;2*1H/q+2;;/p-2

Standard InChI Key:  FAPSXSAPXXJTOU-UHFFFAOYSA-L

Molfile:  

     RDKit          2D

 16 13  0  0  0  0  0  0  0  0999 V2000
    2.7250    0.9833    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.3667   -0.8292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3583   -0.4917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3875   -1.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4167   -0.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0667    0.4208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3458    0.0333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8375   -1.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6958    0.7333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8292   -1.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3417   -1.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4375   -0.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4667   -0.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4792   -0.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4500   -0.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8833    1.4250    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0
  4 12  1  0
  5  2  1  0
  6  2  1  0
  7  3  1  0
  8  3  1  0
  9  3  1  0
 10  2  1  0
 11  2  1  0
 12 15  1  0
 13  5  1  0
 14 13  1  0
 15 14  1  0
M  CHG  4   1  -1   2   1   3   1  16  -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: Yes

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 202.39

Molecular Weight (Monoisotopic): 202.2398

AlogP: 1.96

#Rotatable Bonds: 7

Polar Surface Area: 0.00

Molecular Species: ┄

HBA: ┄

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: -6.65

CX LogD: -6.65

Aromatic Rings: ┄

Heavy Atoms: 14

QED Weighted: 0.44

Np Likeness Score: 0.56

References

1. Calas M, Cordina G, Bompart J, Ben Bari M, Jei T, Ancelin ML, Vial H..  (1997)  Antimalarial activity of molecules interfering with Plasmodium falciparum phospholipid metabolism. Structure-activity relationship analysis.,  40  (22): [PMID:9357523] [10.1021/jm9701886]

2. Gu Y, Lee H, Hudson RA..  (1994)  Bis-catechol-substituted redox-reactive analogues of hexamethonium and decamethonium: stimulated affinity-dependent reactivity through iron peroxide catalysis.,  37  (25): [PMID:7996555] [10.1021/jm00051a021]

3. Calas M, Ancelin ML, Cordina G, Portefaix P, Piquet G, Vidal-Sailhan V, Vial H..  (2000)  Antimalarial activity of compounds interfering with Plasmodium falciparum phospholipid metabolism: comparison between mono- and bisquaternary ammonium salts.,  43  (3): [PMID:10669577] [10.1021/jm9911027]

4. Tischer M, Sologub L, Pradel G, Holzgrabe U..  (2010)  The bisnaphthalimides as new active lead compounds against Plasmodium falciparum.,  18  (9): [PMID:20382538] [10.1016/j.bmc.2010.03.067]

5. Diamandis P, Wildenhain J, Clarke ID, Sacher AG, Graham J, Bellows DS, Ling EK, Ward RJ, Jamieson LG, Tyers M, Dirks PB..  (2007)  Chemical genetics reveals a complex functional ground state of neural stem cells.,  3  (5): [PMID:17417631] [10.1038/nchembio873]

6. PubChem BioAssay data set, 

7. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

8. PubChem BioAssay data set, 

9. PubChem BioAssay data set, 

10. De Bruyn T, van Westen GJ, Ijzerman AP, Stieger B, de Witte P, Augustijns PF, Annaert PP..  (2013)  Structure-based identification of OATP1B1/3 inhibitors.,  83  (6): [PMID:23571415] [10.1124/mol.112.084152]

11. 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]

12. 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]

13. 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(4):

• Scientific Literature
• PubChem BioAssays
• USP Dictionary of USAN and International Drug Names
• SARS-CoV-2 Screening Data 2020-21