ID: ALA2228155

Max Phase: Preclinical

Molecular Formula: C7H14N4O3

Molecular Weight: 202.21

Molecule Type: Small molecule

Representations

Canonical SMILES:  CN/C(=N/CC1CCOC1)N[N+](=O)[O-]

Standard InChI:  InChI=1S/C7H14N4O3/c1-8-7(10-11(12)13)9-4-6-2-3-14-5-6/h6H,2-5H2,1H3,(H2,8,9,10)

Standard InChI Key:  YKBZOVFACRVRJN-UHFFFAOYSA-N

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

Properties

Molecular Weight: 202.21

Molecular Weight (Monoisotopic): 202.1066

AlogP: -0.62

#Rotatable Bonds: 3

Polar Surface Area: 88.79

Molecular Species: BASE

HBA: 4

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 8.41

CX Basic pKa: 11.43

CX LogP: -0.75

CX LogD: -1.75

Aromatic Rings: 0

Heavy Atoms: 14

QED Weighted: 0.28

Np Likeness Score: -0.19

References

1. Ford KA, Gulevich AG, Swenson TL, Casida JE..  (2011)  Neonicotinoid insecticides: oxidative stress in planta and metallo-oxidase inhibition.,  59  (9): [PMID:21476569] [10.1021/jf200485k]

2. Ohno I, Tomizawa M, Durkin KA, Casida JE, Kagabu S..  (2009)  Neonicotinoid substituents forming a water bridge at the nicotinic acetylcholine receptor.,  57  (6): [PMID:19253973] [10.1021/jf803985r]

3. Wakita T..  (2011)  Molecular design of dinotefuran with unique insecticidal properties.,  59  (7): [PMID:20919736] [10.1021/jf1030778]

4. Wakita T, Kinoshita K, Yasui N, Yamada E, Kawahara N, Kodaka K.  (2004)  Synthesis and Structure-Activity Relationships of Dinotefuran Derivatives: Modification in the Nitroguanidine Part,  29  (4): [10.1584/jpestics.29.348]

5. Wakita T, Kinoshita K, Kodaka K, Yasui N, Naoi A, Banba S.  (2004)  Synthesis and Structure-Activity Relationships of Dinotefuran Derivatives: Modification in the Tetrahydro-3-furylmethyl Part,  29  (4): [10.1584/jpestics.29.356]

6. Zhang A, Kayser H, Maienfisch P, Casida JE..  (2000)  Insect nicotinic acetylcholine receptor: conserved neonicotinoid specificity of [(3)H]imidacloprid binding site.,  75  (3): [PMID:10936213] [10.1046/j.1471-4159.2000.751294.x]

7. Yokoyama A, Ohtsu K, Iwafune T, Nagai T, Ishihara S, Kobara Y, Horio T, Endo S.  (2009)  A useful new insecticide bioassay using first-instar larvae of a net-spinning caddisfly, Cheumatopsyche brevilineata (Trichoptera: Hydropsychidae),  34  (1): [10.1584/jpestics.G08-26]

8. Morales-Rodriguez A, Ospina A, Peck DC..  (2010)  Variation in the laboratory susceptibility of turf-infesting white grubs (Coleoptera: Scarabaeidae) to biological, biorational and chemical control products.,  66  (1): [PMID:19742452] [10.1002/ps.1835]

9. KAGABU S, MATSUDA K, KOMAI K.  (2002)  Preparation of Dinotefuran Related Compounds and Agonistic Action on SAD2 Hybrid Nicotinic Acetylcholine Receptors Expressed in Xenopus laevis Oocytes,  27  (4): [10.1584/jpestics.27.374]

10. Wakita T, Yasui N, Yamada E, Kishi D.  (2005)  Development of a Novel Insecticide, Dinotefuran,  30  (2): [10.1584/jpestics.30.122]

11. Shi X, Jiang L, Wang H, Qiao K, Wang D, Wang K..  (2011)  Toxicities and sublethal effects of seven neonicotinoid insecticides on survival, growth and reproduction of imidacloprid-resistant cotton aphid, Aphis gossypii.,  67  (12): [PMID:21714058] [10.1002/ps.2207]

12. Cutler P, Slater R, Edmunds AJ, Maienfisch P, Hall RG, Earley FG, Pitterna T, Pal S, Paul VL, Goodchild J, Blacker M, Hagmann L, Crossthwaite AJ..  (2013)  Investigating the mode of action of sulfoxaflor: a fourth-generation neonicotinoid.,  69  (5): [PMID:23112103] [10.1002/ps.3413]

13. PubChem BioAssay data set, 

Source

Source(2):

• Scientific Literature
• PubChem BioAssays