Showing Compound Card for Azoxystrobin (CDB006202)

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Record Information
Version1.0
Created at2020-07-28 20:15:29 UTC
Updated at2020-11-18 16:40:14 UTC
CannabisDB IDCDB006202
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameAzoxystrobin
DescriptionMETHYL (2Z)-2-(2-{[6-(2-CYANOPHENOXY)PYRIMIDIN-4-YL]OXY}PHENYL)-3-METHOXYACRYLATE, also known as methyl (e)-2-[2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl]-3-methoxyacrylate, belongs to the class of organic compounds known as phenyl-beta-methoxyacrylates. These are aromatic compounds containing a methyl-3-methoxyacrylate moiety that carries a benzyl group at the C-alpha carbon. As a result, the electron transport chain is disrupted and the cell can no longer aerobically produce ATP for energy. Azoxystrobin possesses the broadest spectrum of activity of all known antifungals. Cyanide binds to the ferric ion of methemoglobin to form inactive cyanmethemoglobin. METHYL (2Z)-2-(2-{[6-(2-CYANOPHENOXY)PYRIMIDIN-4-YL]OXY}PHENYL)-3-METHOXYACRYLATE is an extremely weak basic (essentially neutral) compound (based on its pKa). METHYL (2Z)-2-(2-{[6-(2-CYANOPHENOXY)PYRIMIDIN-4-YL]OXY}PHENYL)-3-METHOXYACRYLATE is a potentially toxic compound. Cyanide metabolites are excreted in the urine. Organic nitriles decompose into cyanide ions both in vivo and in vitro. Cyanide is rapidly absorbed and distributed throughout the body.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(AlphaE)-2-[[6-(2-cyanophenoxy)-4-pyrimidinyl]oxy]-alpha-(methoxymethylene) benzeneacetic acid methyl esterChEBI
Methyl (e)-2-[2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl]-3-methoxyacrylateChEBI
(AlphaE)-2-[[6-(2-cyanophenoxy)-4-pyrimidinyl]oxy]-a-(methoxymethylene) benzeneacetate methyl esterGenerator
(AlphaE)-2-[[6-(2-cyanophenoxy)-4-pyrimidinyl]oxy]-a-(methoxymethylene) benzeneacetic acid methyl esterGenerator
(AlphaE)-2-[[6-(2-cyanophenoxy)-4-pyrimidinyl]oxy]-alpha-(methoxymethylene) benzeneacetate methyl esterGenerator
(AlphaE)-2-[[6-(2-cyanophenoxy)-4-pyrimidinyl]oxy]-α-(methoxymethylene) benzeneacetate methyl esterGenerator
(AlphaE)-2-[[6-(2-cyanophenoxy)-4-pyrimidinyl]oxy]-α-(methoxymethylene) benzeneacetic acid methyl esterGenerator
Methyl (e)-2-[2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl]-3-methoxyacrylic acidGenerator
METHYL (2Z)-2-(2-{[6-(2-cyanophenoxy)pyrimidin-4-yl]oxy}phenyl)-3-methoxyacrylic acidGenerator
ICIA-5504MeSH
Azoxy-strobinMeSH
AmistarMeSH
ICIA 5504MeSH
Methyl (2E)-2-(2-(6-(2-cyanophenoxy)pyrimidin-4-yloxy)phenyl)-3-methoxyacrylateMeSH
Chemical FormulaC22H17N3O5
Average Molecular Weight403.3875
Monoisotopic Molecular Weight403.116820669
IUPAC Namemethyl (2E)-2-(2-{[6-(2-cyanophenoxy)pyrimidin-4-yl]oxy}phenyl)-3-methoxyprop-2-enoate
Traditional Nameazoxystrobin
CAS Registry Number131860-33-8
SMILES
CO\C=C(\C(=O)OC)C1=CC=CC=C1OC1=NC=NC(OC2=CC=CC=C2C#N)=C1
InChI Identifier
InChI=1S/C22H17N3O5/c1-27-13-17(22(26)28-2)16-8-4-6-10-19(16)30-21-11-20(24-14-25-21)29-18-9-5-3-7-15(18)12-23/h3-11,13-14H,1-2H3/b17-13+
InChI KeyWFDXOXNFNRHQEC-GHRIWEEISA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenyl-beta-methoxyacrylates. These are aromatic compounds containing a methyl-3-methoxyacrylate moiety that carries a benzyl group at the C-alpha carbon.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenyl-beta-methoxyacrylates
Direct ParentPhenyl-beta-methoxyacrylates
Alternative Parents
Substituents
  • Phenyl-beta-methoxyacrylate
  • Diaryl ether
  • Benzonitrile
  • Phenoxy compound
  • Phenol ether
  • Styrene
  • Pyrimidine
  • Methyl ester
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Vinylogous ester
  • Heteroaromatic compound
  • Carboxylic acid ester
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Ether
  • Monocarboxylic acid or derivatives
  • Carbonitrile
  • Nitrile
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Not Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.67ALOGPS
logP4.22ChemAxon
logS-4.8ALOGPS
pKa (Strongest Basic)0.94ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area103.56 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity108.74 m³·mol⁻¹ChemAxon
Polarizability39.77 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0006-1419000000-94a465d21aa17ab2e1f42014-10-20View Spectrum
GC-MSAzoxystrobin, non-derivatized, GC-MS Spectrumsplash10-0006-6629000000-21ca8c121fc5f3610f9dSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0fk9-0009700000-8f7e9e7270c633ff2c3b2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00di-0009000000-f90c3fb664941cf734b02017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-006x-0009000000-4490024fd34fec142c872017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-0119000000-f7f4f6973d3504b2ca3b2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0fir-0925000000-ac2b9a7260666b73027a2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00di-0009000000-83eaa40df9bdf29c9cc42017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00di-0009100000-2b14ac3ae132dade33362017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00di-0009000000-8a2f4439457c5f73030e2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004l-0119000000-b5fc66d47037333f6e6c2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0fc0-0936000000-b82079f65435e3ad45be2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0kn9-0921000000-d532e80b217c51e4d7ec2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-05fr-0900000000-9e567fc431ad8d9b97202017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00di-0009100000-e15afdd0e3f99e20d9a32017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00di-0009000000-24fb3f512e4362d6367e2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004l-0119000000-e01c0568df01a3c3878d2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0fc0-0946000000-f516220e4e8d1b4ba0542017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0kn9-0921000000-67f8139f3857e48f3f722017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00di-0900000000-9a806ccd261aac6ebd142017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00di-0009000000-3658b25301d356d00ab72017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fb9-0119400000-d665cfdc0b69f49290e12016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gb9-3935400000-8c9c381578aa176d91b72016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gba-4977000000-b5560d3ca110641fa5b62016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0001900000-0d12d3c63b16557797c92016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-3534900000-b28d3e7e5e112b1693b42016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0900-1493000000-abc33139c95df55cfccd2016-08-03View Spectrum
NMR
TypeDescriptionView
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDNot Available
DrugBank IDDB07401
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC18558
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAzoxystrobin
METLIN IDNot Available
PubChem Compound3034285
PDB IDNot Available
ChEBI ID40909
References
General References
  1. 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 ]