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

Associated Items:

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

Associated Targets(Human)

SMN1 Tchem Survival motor neuron protein (34246 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
EHMT2 Tchem Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 (93046 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
KPNB1 Tbio Importin subunit beta-1/Snurportin-1 (25097 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GMNN Tbio Geminin (128009 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CGA Tbio Glycoprotein hormones alpha chain (29278 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PLK1 Tchem Serine/threonine-protein kinase PLK1 (28605 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
APEX1 Tchem DNA-(apurinic or apyrimidinic site) lyase (38016 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
KB (17409 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

ampC Beta-lactamase AmpC (62480 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Plasmodium falciparum (966862 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Aphis craccivora (935 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Periplaneta americana (513 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Nicotinic acetylcholine receptor alpha8 subunit (79 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Nephotettix cincticeps (805 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Acetylcholine-binding protein (240 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Soluble acetylcholine receptor (39 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CHRNA4 Neuronal acetylcholine receptor subunit alpha-4 (14 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
nAChRbeta2 Acetylcholine receptor subunit beta-like 2 (115 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Cnaphalocrocis medinalis (89 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Plutella xylostella (1838 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Spodoptera litura (1708 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Mus musculus (284745 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Laodelphax striatellus (278 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Myzus persicae (1112 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CHRNA1 Acetylcholine receptor protein alpha chain (109 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 254.68Molecular Weight (Monoisotopic): 254.0571AlogP: 1.22#Rotatable Bonds: 3
Polar Surface Area: 71.30Molecular Species: NEUTRALHBA: 5HBD: 1
#RO5 Violations: 0HBA (Lipinski): 6HBD (Lipinski): 1#RO5 Violations (Lipinski): 0
CX Acidic pKa: CX Basic pKa: 1.56CX LogP: 1.35CX LogD: 1.35
Aromatic Rings: 1Heavy Atoms: 17QED Weighted: 0.50Np 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]