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CHEBI:133859 - afidopyropen

ChEBI IDCHEBI:133859
ChEBI Nameafidopyropen
Stars
DefinitionAn organic heterotetracyclic compound that is 1,3,4,4a,5,6,6a,12,12a,12b-decahydro-2H,11H-benzo[f]pyrano[4,3-b]chromen-11-one which is substituted by methyl groups at positions 4, 6a, and 12b; hydroxy groups at positions 3, 6, and 9; and a cyclopropycarbonyloxymethyl group and a cyclopropylcarbonyloxy group at positions 17 and 18 respectively, and a pyridin-3-yl group at position 14 (the (3S,4R,4aR,6S,6aS,12R,12aS,12bS stereoisomer). It is an insecticide that is effective against sucking insects on fruit, vegetables and nuts.
Last Modified14 March 2024
SubmitterGareth Owen
DownloadsMolfile
FormulaC33H39NO9
Net Charge0
Average Mass593.673
Monoisotopic Mass593.26248
SMILES[H][C@@]12C[C@H](O)[C@@]3(C)Oc4cc(-c5cccnc5)oc(=O)c4[C@H](O)[C@]3([H])[C@@]1(C)CC[C@H](OC(=O)C1CC1)[C@@]2(C)COC(=O)C1CC1
InChIInChI=1S/C33H39NO9/c1-31-11-10-24(42-29(38)18-8-9-18)32(2,16-40-28(37)17-6-7-17)22(31)14-23(35)33(3)27(31)26(36)25-21(43-33)13-20(41-30(25)39)19-5-4-12-34-15-19/h4-5,12-13,15,17-18,22-24,26-27,35-36H,6-11,14,16H2,1-3H3/t22-,23+,24+,26+,27-,31+,32+,33-/m1/s1
InChIKeyLRZWFURXIMFONG-HRSIRGMGSA-N
Roles Classification
Biological Role:
TRPV channel modulator  Any transient receptor potential (TRP) channel modulator that modulates the TRPV channels (V = vanilloid). There is strong evidence that action at one or more of this class of proteins is responsible for the insecticidal action of pymetrozine, pyrifluquinazon, and afidopyropen.
Applications:
insecticide  Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.
agrochemical  An agrochemical is a substance that is used in agriculture or horticulture.
ChEBI Ontology
Outgoing Relation(s)
afidopyropen (CHEBI:133859) has role agrochemical (CHEBI:33286)
afidopyropen (CHEBI:133859) has role insecticide (CHEBI:24852)
afidopyropen (CHEBI:133859) has role TRPV channel modulator (CHEBI:142782)
afidopyropen (CHEBI:133859) is a cyclopropanecarboxylate ester (CHEBI:50351)
afidopyropen (CHEBI:133859) is a organic heterotetracyclic compound (CHEBI:38163)
afidopyropen (CHEBI:133859) is a pyridines (CHEBI:26421)
afidopyropen (CHEBI:133859) is a secondary alcohol (CHEBI:35681)
IUPAC Name 
[(3S,4R,4aR,6S,6aS,12R,12aS,12bS)-3-[(cyclopropylcarbonyl)oxy]-6,12-dihydroxy-4,6a,12b-trimethyl-11-oxo-9-(pyridin-3-yl)-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-2H,11H-benzo[f]pyrano[4,3-b]chromen-4-yl]methyl cyclopropanecarboxylate
Synonyms  Source
[(3S,4R,4aR,6S,6aS,12R,12aS,12bS)-3-(cyclopropylcarbonyloxy)-1,2,3,4,4a,5,6,6a,12a,12b-decahydro-6,12-dihydroxy-4,6a,12b-trimethyl-11-oxo-9-(3-pyridyl)-11H,12H-benzo[f]pyrano[4,3-b]chromen-4-yl]methyl cyclopropanecarboxylateAlan Wood's Pesticides
afidopyropèneChEBI
[(3S,4R,4aR,6S,6aS,12R,12aS,12bS)-3-[(cyclopropylcarbonyl)oxy]-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-6,12-dihydroxy-4,6a,12b-trimethyl-11-oxo-9-(3-pyridinyl)-2H,11H-naphtho[2,1-b]pyrano[3,4-e]pyran-4-yl]methyl cyclopropanecarboxylateAlan Wood's Pesticides
Manual XrefsDatabases
afidopyropenAlan Wood's Pesticides
EP2119361Patent
2636PPDB
Registry NumbersSources
Reaxys:21172253Reaxys
CAS:915972-17-7Alan Wood's Pesticides
Citations