methyl (2E)-2-(2-{[6-(2-cyanophenoxy)pyrimidin-4-yl]oxy}phenyl)-3-methoxyprop-2-enoate

• ChemBase ID: 5050
• Molecular Formular: C22H17N3O5
• Molecular Mass: 403.38748
• Monoisotopic Mass: 403.11682066
• SMILES: N#Cc1ccccc1Oc1cc(ncn1)Oc1ccccc1/C(=C\OC)/C(=O)OC
• Canonical SMILES: CO/C=C(\c1ccccc1Oc1ncnc(c1)Oc1ccccc1C#N)/C(=O)OC
• InChI: 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+
• InChIKey: WFDXOXNFNRHQEC-GHRIWEEISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2E)-2-(2-{[6-(2-cyanophenoxy)pyrimidin-4-yl]oxy}phenyl)-3-methoxyprop-2-enoate; methyl 2-(2-{[6-(2-cyanophenoxy)pyrimidin-4-yl]oxy}phenyl)-3-methoxyprop-2-enoate
• IUPAC Traditional name: azoxystrobin; methyl 2-(2-{[6-(2-cyanophenoxy)pyrimidin-4-yl]oxy}phenyl)-3-methoxyprop-2-enoate
• Synonyms: METHYL (2Z)-2-(2-{[6-(2-CYANOPHENOXY)PYRIMIDIN-4-YL]OXY}PHENYL)-3-METHOXYACRYLATE; Azoxystrobin; (αE)-2-[[6-(2-Cyanophenoxy)-4-pyrimidinyl]oxy]-α-(methoxymethylene)benzeneacetic Acid Methyl Ester; Methyl (E)-2-[2-[6-(2-Cyanophenoxy)pyrimidin-4-yloxy]phenyl]-3-methoxypropenoate; Abound; Cruiser Extreme; Dynasty; Ortiva; Priori; Protege; Protege FL; Azoxystrobine; Heritage; Amistar; Quadris; Bankit; Azoxystrobin; 嘧菌酯

Database IDs

• CAS Number: 131860-33-8
• MDL Number: MFCD08277047
• PubChem SID: 99443872; 24869873; 160968481
• PubChem CID: 3034285
• CHEMBL: 230001
• Chemspider ID: 2298772
• DrugBank ID: DB07401
• KEGG ID: C18558
• Wikipedia Title: Azoxystrobin
• Color Index Number: 23860

CALCULATED PROPERTIES

JChem

• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): 4.224741
• LogD (pH = 7.4): 4.2247524
• Log P: 4.2247524
• Molar Refractivity: 108.736 cm^3
• Polarizability: 41.536648 Å^3
• Polar Surface Area: 103.56 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.67
• LOG S: -4.82
• Solubility (Water): 6.18e-03 g/l

PROPERTIES

Safety Information

• European Hazard Symbols: Nature polluting (N); Toxic (T)
• UN Number: 2811
• German water hazard class: 2
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 23-50/53
• Safety Statements: 22-45-60-61
• GHS Pictograms: GHS06; GHS09
• GHS Signal Word: Danger
• GHS Hazard statements: H331-H410
• GHS Precautionary statements: P261-P273-P311-P501
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 3

Product Information

• Grade: PESTANAL®, analytical standard
• Empirical Formula (Hill Notation): C22H17N3O5

DETAILS

DrugBank - DB07401

Drug information: experimental

Sigma Aldrich - 31697

Legal Information
PESTANAL is a registered trademark of Sigma-Aldrich Laborchemikalien GmbH

Toronto Research Chemicals - A965150

Strobilurin fungicide; inhibits mitochondrial respiration by blocking electron transfer between cytochromes b and c1. Agricultural fungicide.

REFERENCES

• Smalling, K., et al.: Environ. Toxicol. Chem., 29, 2593 (2010)
• Lu, X., et al.: Phytopathol., 100, 1162 (2010)
• Schafer, R., et al.: Environ. Sci. Technol., 45, 1665 (2010)