SID22413311

ID: ALA1391421

Chembl Id: CHEMBL1391421

Cas Number: 101336-63-4

PubChem CID: 6506573

Max Phase: Preclinical

Molecular Formula: C10H11ClN4O2

Molecular Weight: 254.68

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=[N+]([O-])/C=C1\NCCN1Cc1ccc(Cl)nc1

Standard InChI:  InChI=1S/C10H11ClN4O2/c11-9-2-1-8(5-13-9)6-14-4-3-12-10(14)7-15(16)17/h1-2,5,7,12H,3-4,6H2/b10-7+

Standard InChI Key:  ALNDHUQPXHHNON-JXMROGBWSA-N

Alternative Forms

1. Parent:

   

   ALA1391421

   Pyridine, 2-chloro-5-[[2-(nitromethylene)-1-imidazolidinyl]methyl]-

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: 254.68

Molecular Weight (Monoisotopic): 254.0571

AlogP: 1.22

#Rotatable Bonds: 3

Polar Surface Area: 71.30

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa: 1.56

CX LogP: 1.35

CX LogD: 1.35

Aromatic Rings: 1

Heavy Atoms: 17

QED Weighted: 0.50

Np Likeness Score: -1.23

References

1. PubChem BioAssay data set, 

2. PubChem BioAssay data set, 

3. Kagabu S..  (2011)  Discovery of imidacloprid and further developments from strategic molecular designs.,  59  (7): [PMID:20718435] [10.1021/jf101824y]

4. Akamatsu M..  (2011)  Importance of physicochemical properties for the design of new pesticides.,  59  (7): [PMID:20879794] [10.1021/jf102525e]

5. Tomizawa M, Casida JE..  (2011)  Unique neonicotinoid binding conformations conferring selective receptor interactions.,  59  (7): [PMID:21341671] [10.1021/jf1019455]

6. Tian Z, Jiang Z, Li Z, Song G, Huang Q..  (2007)  Syntheses and biological activities of octahydro-1H-cyclopenta[d]pyrimidine derivatives.,  55  (1): [PMID:17199325] [10.1021/jf062845l]

7. Kagabu S, Ishihara R, Hieda Y, Nishimura K, Naruse Y..  (2007)  Insecticidal and neuroblocking potencies of variants of the imidazolidine moiety of imidacloprid-related neonicotinoids and the relationship to partition coefficient and charge density on the pharmacophore.,  55  (3): [PMID:17263479] [10.1021/jf0623440]

8. Shiokawa K, Moriya K, Shibuya K, Hattori Y, Tsuboi S, Kagabu S.  (1992)  3-(6-Chloronicotinyl)-2-nitromethylene-thiazolidine as a New Class of Insecticide Acting against Lepidoptera Species,  56  (8): [10.1271/bbb.56.1364]

9. KOYANAGI T, MORITA M, OKADA H.  (2000)  Insecticidal Activity and Selective Toxicity of Chloronicotinyl Compounds Having Thiomethyl Groups,  25  (1): [10.1584/jpestics.25.37]

10. Kagabu S, Moriya K, Shibuya K, Hattori Y, Tsuboi S, Kozo S.  (1992)  1-(6-Halonicotinyl)-2-nitromethylene-imidazolidines as Potential New Insecticides,  56  (2): [10.1271/bbb.56.362]

11. Moriya K, Shibuya K, Hattori Y, Tsuboi S, Shiokawa K, Kagabu S.  (1992)  1-(6-Chloronicotinyl)-2-nitroimino-imidazolidines and Related Compounds as Potential New Insecticides,  56  (2): [10.1271/bbb.56.364]

12. Moriya K, Shibuya K, Hattori Y, Tsuboi S, Shiokawa K, Kagabu S..  (1993)  Structural Modification of the 6-Chloropyridyl Moiety in the Imidacloprid, Skeleton: Introduction of a Five-membered Heteroaromatic Ring and the Resulting Insecticidal Activity.,  57  (1): [PMID:27316887] [10.1271/bbb.57.127]

13. Ihara M, Brown LA, Ishida C, Okuda H, Sattelle DB, Matsuda K.  (2006)  Actions of imidacloprid, clothianidin and related neonicotinoids on nicotinic acetylcholine receptors of American cockroach neurons and their relationships with insecticidal potency,  31  (1): [10.1584/jpestics.31.35]

14. TOMIZAWA M, OTSUKA H, MIYAMOTO T, YAMAMOTO I.  (1995)  Pharmacological Effects of Imidacloprid and Its Related Compounds on the Nicotinic Acetyicholine Receptor with Its Ion Channel from the Torpedo Electric Organ,  20  (1): [10.1584/jpestics.20.49]

15. TOMIZAWA M, OTSUKA H, MIYAMOTO T, ELDEFRAWI ME, YAMAMOTO I.  (1995)  Pharmacological Characteristics of Insect Nicotinic Acetyicholine Receptor with Its Ion Channel and the Comparison of the Effect of Nicotinoids and Neonicotinoids,  20  (1): [10.1584/jpestics.20.57]

16. Kagabu S.  (2008)  Pharmacophore of neonicotinoid insecticides,  33  (1): [10.1584/jpestics.R07-05]

17. Kemker I,Schröder DC,Feiner RC,Müller KM,Marion A,Sewald N.  (2021)  Tuning the Biological Activity of RGD Peptides with Halotryptophans†.,  64  (1.0): [PMID:33356253] [10.1021/acs.jmedchem.0c01536]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays