Cannabis Compound Database: Showing Compound Card for Clothianidin (CDB006206)

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Record Information

Version

1.0

Created at

2020-07-28 20:15:43 UTC

Updated at

2020-11-18 16:40:14 UTC

CannabisDB ID

CDB006206

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Clothianidin

Description

Clothianidin belongs to the class of organic compounds known as 2,5-disubstituted thiazoles. 2,5-disubstituted thiazoles are compounds containing a thiazole ring substituted at positions 2 and 5 only. Clothianidin is a moderately basic compound (based on its pKa). Clothianidin is a neonicotinoid insecticide, which is a class of neuro-active insecticides modeled after nicotine. Neonicotinoids are currently used on corn, canola, cotton, sorghum, sugar beets and soybeans. Clothianidin is a potentially toxic compound. However, Some neonicotinoid breakdown products are toxic to humans, especially if they have become charged. However, acetylcholinesterase cannot break down neonicotinoids and the binding is irreversible. The low mammalian toxicity of neonicotinoids can be explained in large part by their lack of a charged nitrogen atom at physiological pH. The uncharged molecule can penetrate the insect blood–brain barrier, while the mammalian blood–brain barrier filters it. While low to moderate activation of these receptors causes nervous stimulation, high levels overstimulate and block the receptors causing paralysis and death.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
(e)-N-(2-Chloro-5-thiazolyl)methyl-n'-methyl-n''-nitroguanidine	ChEBI
((e)-1-(2-chloro-1,3-Thiazol-5-ylmethyl)-3-methyl-2-nitroguanidine)	MeSH

Chemical Formula

C₆H₈ClN₅O₂S

Average Molecular Weight

249.678

Monoisotopic Molecular Weight

249.008722922

IUPAC Name

(E)-N'-[(2-chloro-1,3-thiazol-5-yl)methyl]-N-methyl-N''-nitroguanidine

Traditional Name

celero

CAS Registry Number

210880-92-5

SMILES

CN\C(NCC1=CN=C(Cl)S1)=N/[N+]([O-])=O

InChI Identifier

InChI=1S/C6H8ClN5O2S/c1-8-6(11-12(13)14)10-3-4-2-9-5(7)15-4/h2H,3H2,1H3,(H2,8,10,11)

InChI Key

PGOOBECODWQEAB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2,5-disubstituted thiazoles. 2,5-Disubstituted thiazoles are compounds containing a thiazole ring substituted at positions 2 and 5 only.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azoles

Sub Class

Thiazoles

Direct Parent

2,5-disubstituted thiazoles

Alternative Parents

Substituents

2,5-disubstituted 1,3-thiazole
Nitroguanidine
Aryl chloride
Aryl halide
Nitramine
Heteroaromatic compound
Guanidine
Organic nitro compound
Carboximidamide
Allyl-type 1,3-dipolar organic compound
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Azacycle
Organic nitrogen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Hydrocarbon derivative
Imine
Organic zwitterion
Organic oxygen compound
Organopnictogen compound
Organic oxide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

organochlorine compound (CHEBI:39178 )
1,3-thiazole (CHEBI:39178 )
2-nitroguanidine derivative (CHEBI:39178 )
Neonicotinoid insecticides (C18508 )

Ontology

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
logP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	0.62	ALOGPS
logP	0.54	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Basic)	0.41	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	92.45 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	55.53 m³·mol⁻¹	ChemAxon
Polarizability	22.17 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Clothianidin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Clothianidin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT 17V, positive	splash10-014i-0910000000-6385f1a3a7f91ed7e982	2020-08-04	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT 7V, positive	splash10-0gc0-0950000000-d29e3319f44939e2ffe7	2020-08-04	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT 14V, positive	splash10-0159-0900000000-653b260bb023add99e31	2020-08-04	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT 22V, positive	splash10-00lr-0900000000-b5f88b04d76924d17378	2020-08-04	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT 29V, positive	splash10-01q9-0900000000-ed2f06c069aed87e9f9e	2020-08-04	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT 37V, positive	splash10-03e9-0900000000-f9169babd128a490c689	2020-08-04	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT 44V, positive	splash10-03e9-2900000000-84040d7ff64bca37fde8	2020-08-04	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT 17V, positive	splash10-0159-0900000000-97745f6dc45dd1581765	2020-08-04	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ 10V, positive	splash10-014i-0920000000-fec4e86ce184bd252665	2020-08-04	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ 20V, positive	splash10-02u0-0900000000-c422082c73e9f46c2713	2020-08-04	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ 30V, positive	splash10-03e9-0900000000-d266e4d6dacfa337ada0	2020-08-04	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ 40V, positive	splash10-03di-0900000000-019d795fba7ac99240cf	2020-08-04	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 10V, positive	splash10-0gb9-0940000000-d3f42327bbe9eaebd932	2020-08-04	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 20V, positive	splash10-0159-0900000000-b753f5e40fab4c8f7092	2020-08-04	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 30V, positive	splash10-00lr-0900000000-c9321c59320cacc256da	2020-08-04	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 40V, positive	splash10-001i-0900000000-11d29a227bda097d127c	2020-08-04	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 50V, positive	splash10-001i-0900000000-7e088dfb25fbf5322cae	2020-08-04	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 24V, positive	splash10-0159-0900000000-66c374cc807fdd5fc988	2020-08-04	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT 17V, negative	splash10-02t9-0910000000-6ad88fdea0ea1ddc8781	2020-08-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0090000000-cf623673de668657f311	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udl-0190000000-392883a85c2c2015b0c3	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-044i-9500000000-499b35d8d5d2f169387d	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-4090000000-770d5ba68ba065242bf7	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-2190000000-82b6362d6ef9385de1d2	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0bti-9200000000-2b339e51e2cf38532f75	2016-08-03	View Spectrum

NMR

Not Available

Pathways

Not Available

Protein Targets

Enzymes

Not Available

Transporters

Not Available

Metal Bindings

Not Available

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C18508

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Clothianidin

METLIN ID

Not Available

PubChem Compound

213027

PDB ID

Not Available

ChEBI ID

39177

References

General References

Taylor A, Birkett JW: Pesticides in cannabis: A review of analytical and toxicological considerations. Drug Test Anal. 2020 Feb;12(2):180-190. doi: 10.1002/dta.2747. Epub 2020 Jan 19. [PubMed:31834671 ]

Showing Compound Card for Clothianidin (CDB006206)

Structure for CDB006206 (Clothianidin)