CHEBI:133859 - afidopyropen

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ChEBI Name afidopyropen
ChEBI ID CHEBI:133859
Definition An 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C33H39NO9
Net Charge 0
Average Mass 593.665
Monoisotopic Mass 593.26248
InChI InChI=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
InChIKey LRZWFURXIMFONG-HRSIRGMGSA-N
SMILES C1(CC1)C(=O)OC[C@]2([C@]3([C@@]([C@@]4([C@](OC5=C([C@@H]4O)C(OC(=C5)C=6C=NC=CC6)=O)([C@H](C3)O)C)[H])(CC[C@@H]2OC(=O)C7CC7)C)[H])C
Roles Classification
Biological Role(s): 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.
Application(s): 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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 Sources
[(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 cyclopropanecarboxylate Alan Wood's Pesticides
[(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 cyclopropanecarboxylate Alan Wood's Pesticides
afidopyropène ChEBI
Manual Xrefs Databases
2636 PPDB
afidopyropen Alan Wood's Pesticides
EP2119361 Patent
View more database links
Registry Numbers Types Sources
21172253 Reaxys Registry Number Reaxys
915972-17-7 CAS Registry Number Alan Wood's Pesticides
Citations Waiting for Citations Types Sources
36087889 PubMed citation Europe PMC
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IND607900164 Agricola citation Europe PMC
IND608058943 Agricola citation Europe PMC
IND608078350 Agricola citation Europe PMC
Last Modified
14 March 2024