1-(4-Amino-2-propyl-pyrimidin-5-ylmethyl)-2-methyl-pyridinium chloride

ID: ALA1318296

Cas Number: 3053-18-7

PubChem CID: 8732

Product Number: A421432, Order Now?

Max Phase: Phase

Molecular Formula: C14H20Cl2N4

Molecular Weight: 243.33

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Amprocidum | Amprol | Amprolium hydrochloride | Amprovine | Corid | Mepyrium | Thiacoccid | NSC-523454 | Amprolium hydrochloride|137-88-2|Amprolium HCl|amprolium|Mepyrium|Amprol|Thiacoccid|Amprovine|Amprol 25|Amprolsol vet|Corid vet|Amprol 25 per cent|Corid 20%|Amprolium (hydrochloride)|Corid|1-((4-Amino-2-propylpyrimidin-5-yl)methyl)-2-methylpyridin-1-ium chloride hydrochloride|EINECS 205-307-5|NSC 523454|UNII-95CO6N199Q|AMPROCIDUM|3053-18-7|DTXSID0045547|95CO6N199Q|NSC-523454|DTXCID8025547|1-(Show More⌵

Canonical SMILES:  CCCc1ncc(C[n+]2ccccc2C)c(N)n1.Cl.[Cl-]

Standard InChI:  InChI=1S/C14H19N4.2ClH/c1-3-6-13-16-9-12(14(15)17-13)10-18-8-5-4-7-11(18)2;;/h4-5,7-9H,3,6,10H2,1-2H3,(H2,15,16,17);2*1H/q+1;;/p-1

Standard InChI Key:  PJBQYZZKGNOKNJ-UHFFFAOYSA-M

Molfile:  

     RDKit          2D

 20 19  0  0  0  0  0  0  0  0999 V2000
   -0.3969   -6.6000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0320   -4.1250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3969   -4.1250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7465   -5.3625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3175   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0320   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3175   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3175   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3969   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3969   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1114   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1114   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3175   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8259   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8259   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3175   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0320   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0320   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.2393    0.0000    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  0
  1 10  2  0
  1 11  1  0
  2  6  2  0
  2  8  1  0
  3  8  2  0
  3  9  1  0
  4  6  1  0
  5  6  1  0
  5  7  1  0
  5  9  2  0
  8 13  1  0
 10 12  1  0
 10 16  1  0
 11 14  2  0
 12 15  2  0
 13 17  1  0
 14 15  1  0
 17 18  1  0
M  CHG  2   1   1  19  -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: 243.33

Molecular Weight (Monoisotopic): 243.1604

AlogP: 1.66

#Rotatable Bonds: 4

Polar Surface Area: 55.68

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 5.33

CX LogP: -2.31

CX LogD: -2.31

Aromatic Rings: 2

Heavy Atoms: 18

QED Weighted: 0.83

Np Likeness Score: -0.88

References

1. Bochis RJ, Chabala JC, Harris E, Peterson LH, Barash L, Beattie T, Brown JE, Graham DW, Waksmunski FS, Tischler M..  (1991)  Benzylated 1,2,3-triazoles as anticoccidiostats.,  34  (9): [PMID:1895303] [10.1021/jm00113a024]

2. Wang CC..  (1984)  Parasite enzymes as potential targets for antiparasitic chemotherapy.,  27  (1): [PMID:6317859] [10.1021/jm00367a001]

3. González-Díaz H, Olazábal E, Santana L, Uriarte E, González-Díaz Y, Castañedo N..  (2007)  QSAR study of anticoccidial activity for diverse chemical compounds: prediction and experimental assay of trans-2-(2-nitrovinyl)furan.,  15  (2): [PMID:17081758] [10.1016/j.bmc.2006.10.032]

4. PubChem BioAssay data set, 

5. PubChem BioAssay data set, 

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. Franck Touret, Magali Gilles, Karine Barral, Antoine Nougairède, Etienne Decroly, Xavier de Lamballerie, Bruno Coutard.  (2020)  In vitro screening of a FDA approved chemical library reveals potential inhibitors of SARS-CoV-2 replication,  [10.1101/2020.04.03.023846]

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