Paraquat

ID: ALA74469

Chembl Id: CHEMBL74469

Cas Number: 4685-14-7

PubChem CID: 15939

Max Phase: Preclinical

Molecular Formula: C12H14N2+2

Molecular Weight: 186.26

Molecule Type: Small molecule

Names and Identifiers

Synonyms from Alternative Forms(2): Methyl Viologen | Paraquat

Canonical SMILES:  C[n+]1ccc(-c2cc[n+](C)cc2)cc1

Standard InChI:  InChI=1S/C12H14N2/c1-13-7-3-11(4-8-13)12-5-9-14(2)10-6-12/h3-10H,1-2H3/q+2

Standard InChI Key:  INFDPOAKFNIJBF-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA74469

   PARAQUAT

2. Alternative Forms:

   

   ALA74469

   Methyl viologen dichloride
3. 

   ALA74469

   1,1'-Dimethyl-4,4'-bipyridinium bis(hexafluoro-phosphate)
4. 

   ALA74469

   Paraquat diiodide

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: 186.26

Molecular Weight (Monoisotopic): 186.1146

AlogP: 1.00

#Rotatable Bonds: 1

Polar Surface Area: 7.76

Molecular Species: NEUTRAL

HBA: 0

HBD: 0

#RO5 Violations: 0

HBA (Lipinski): 2

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa:

CX LogP: -6.70

CX LogD: -6.70

Aromatic Rings: 2

Heavy Atoms: 14

QED Weighted: 0.59

Np Likeness Score: -0.04

References

1. Rollema H, Johnson EA, Booth RG, Caldera P, Lampen P, Youngster SK, Trevor AJ, Naiman N, Castagnoli N..  (1990)  In vivo intracerebral microdialysis studies in rats of MPP+ analogues and related charged species.,  33  (8): [PMID:2374149] [10.1021/jm00170a029]

2. Dupont M, James CE, Chevalier J, Pagès JM..  (2007)  An early response to environmental stress involves regulation of OmpX and OmpF, two enterobacterial outer membrane pore-forming proteins.,  51  (9): [PMID:17606680] [10.1128/aac.01481-06]

3. Kularatne SA, Venkatesh C, Santhapuram HK, Wang K, Vaitilingam B, Henne WA, Low PS..  (2010)  Synthesis and biological analysis of prostate-specific membrane antigen-targeted anticancer prodrugs.,  53  (21): [PMID:20936874] [10.1021/jm100729b]

4. Pelletier DJ, Gehlhaar D, Tilloy-Ellul A, Johnson TO, Greene N..  (2007)  Evaluation of a published in silico model and construction of a novel Bayesian model for predicting phospholipidosis inducing potential.,  47  (1): [PMID:17428028] [10.1021/ci6004542]

5. Lowe R, Glen RC, Mitchell JB..  (2010)  Predicting phospholipidosis using machine learning.,  7  (5): [PMID:20799726] [10.1021/mp100103e]

6. Greene N, Fisk L, Naven RT, Note RR, Patel ML, Pelletier DJ..  (2010)  Developing structure-activity relationships for the prediction of hepatotoxicity.,  23  (7): [PMID:20553011] [10.1021/tx1000865]

7. Ekins S, Williams AJ, Xu JJ..  (2010)  A predictive ligand-based Bayesian model for human drug-induced liver injury.,  38  (12): [PMID:20843939] [10.1124/dmd.110.035113]

8. Kruhlak NL, Choi SS, Contrera JF, Weaver JL, Willard JM, Hastings KL, Sancilio LF..  (2008)  Development of a phospholipidosis database and predictive quantitative structure-activity relationship (QSAR) models.,  18  (2): [PMID:20020916] [10.1080/15376510701857262]

9. Pervez H, Manzoor N, Yaqub M, Nasim F, Khan KM.  (2012)  Synthesis and biological evaluation of some N4-substituted 5-nitroisatin-3-thiosemicarbazones,  21  (9): [10.1007/s00044-011-9745-7]

10. Qasem JR..  (2007)  Chemical control of Prosopis farcta (Banks and Sol.) Macbride in the Jordan Valley,  26  (4): [10.1016/j.cropro.2006.04.025]

11. González-Ibarra M, Farfán N, Trejo C, Uribe S, Lotina-Hennsen B..  (2005)  Selective herbicide activity of 2,5-di(benzylamine)-p-benzoquinone against the monocot weed Echinochloa crusgalli. An in vivo analysis of photosynthesis and growth.,  53  (9): [PMID:15853381] [10.1021/jf047883o]

12. Qasem JR..  (2006)  Chemical weed control in seedbed sown onion (Allium cepa L.),  25  (6): [10.1016/j.cropro.2005.09.008]

13. Pervez H, Saira N, Iqbal MS, Yaqub M, Khan KM.  (2013)  Synthesis and biological evaluation of some N 4-aryl-substituted 5-fluoroisatin-3-thiosemicarbazones,  22  (12): [10.1007/s00044-013-0575-7]

14. Holla BS, Rao BS, Shridhara K, Akberali PM..  (2000)  Studies on arylfuran derivatives. Part XI. Synthesis, characterisation and biological studies on some Mannich bases carrying 2,4-dichlorophenylfurfural moiety.,  55  (5): [PMID:10983278] [10.1016/s0014-827x(00)00033-1]

15. Rana P, Naven R, Narayanan A, Will Y, Jones LH.  (2013)  Chemical motifs that redox cycle and their associated toxicity,  4  (8): [10.1039/C3MD00149K]

Source

Source(1):

• Scientific Literature