afidopyropen: a TRPV channel modulator with insecticidal activity; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
afidopyropen : 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. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]
| ID Source | ID |
|---|---|
| PubMed CID | 54589430 |
| CHEBI ID | 133859 |
| SCHEMBL ID | 1280056 |
| Synonym |
|---|
| [(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 |
| [(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 |
| [(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 |
| 915972-17-7 |
| afidopyropen |
| afidopyropene |
| CHEBI:133859 |
| SCHEMBL1280056 |
| afidopyropen [iso] |
| cyclopropanecarboxylic acid, ((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 ester |
| yu794e7qe1 , |
| unii-yu794e7qe1 |
| 1,11-di-o-cyclopropanecarbonyl-1,7,11-trideacetylpyripyropene a |
| me-5343 |
| DTXSID00896889 |
| afidopyropen 100 microg/ml in acetonitrile |
| 1,11-di-o-cyclopropanecarbonyl-1,7,11-trideacetylpyripyropene a; afidopyropen; me 5343 |
| [(1s,2s,5s,6r,7r,9s,10s,18r)-5-(cyclopropanecarbonyloxy)-9,18-dihydroxy-2,6,10-trimethyl-16-oxo-14-pyridin-3-yl-11,15-dioxatetracyclo[8.8.0.02,7.012,17]octadeca-12(17),13-dien-6-yl]methyl cyclopropanecarboxylate |
| E86088 |
Afidopyropen is a derivative of microbial metabolites with pyropene insecticide. It is a novel systemic insecticide with high efficacy against sucking pests, and it is suitable for the management of M.
| Excerpt | Reference | Relevance |
|---|---|---|
| "Afidopyropen is a derivative of microbial metabolites with pyropene insecticide, which has been shown to be effective in the management of" | ( Status of the Resistance of Chen, Z; Cheng, S; Gao, X; Li, R; Liang, P; Zhang, L; Zhang, Y, 2022) | 1.44 |
| "Afidopyropen is a novel systemic insecticide with high efficacy against sucking pests, and it is suitable for the management of M." | ( Persistent toxicity and dissipation dynamics of afidopyropen against the green peach aphid Myzus persicae (Sulzer) in cabbage and chili. Ban, N; Fu, Z; Gao, X; Liang, P; Liu, TX; Liu, X, 2023) | 1.89 |
| "Afidopyropen is a novel biorational insecticide for controlling piercing pests with great potential for application in tea gardens that can form the metabolite M440I007 when utilized for crops. " | ( Method validation for detection of afidopyropen and M440I007 in tea. Chen, Z; Guo, M; Li, Z; Luo, F; Qin, Y; Sun, H; Wang, X; Yang, M; Zhang, X; Zhou, L, 2023) | 2.63 |
| "Afidopyropen is a novel biogenic pesticide widely applied to control sap-feeding pests, and a few studies have evaluated the side effects of afidopyropen on pollinators, excluding the Asian honeybee. " | ( Evaluation of Afidopyropen Toxicity at Environmentally Relevant Doses to the Asian Honeybee ( Ding, Y; Li, J; Pan, Y; Peng, T; Wang, D; Wang, L; Wang, S; Xi, J, 2023) | 2.71 |
| "Afidopyropen is a recently introduced insecticide that provides effective control of insect pests in vegetable crops, including brinjal. " | ( Validation of a QuEChERS-Based Method for the Estimation of Afidopyropen in Brinjal (Solanum Melongena L.) and Soil. Chawla, S; Gor, HN; Patel, HK; Shah, PG; Upadhyay, PP, 2020) | 2.24 |
| "Afidopyropen is an insecticide that acts as a transient receptor potential vanilloid subtype (TRPV) channel modulator in chordotonal organs of target insects and has been assessed for a wide range of toxicity endpoints including chronic toxicity and carcinogenicity in rats and mice. " | ( Afidopyropen: Challenges and impact of a toxicokinetic study designed to identify a point of inflection from dose-proportionality. Doi, A; Fabian, E; Fegert, I; Freeman, E; Frericks, M; Loccisano, AE; Riffle, B, 2021) | 3.51 |
| "Afidopyropen is a novel insecticide that acts as a TRPV channel modulator in chordotonal organs of target insects. " | ( Uterine adenocarcinoma in the rat induced by afidopyropen. An analysis of the lesion's induction, progression and its relevance to humans. Fabian, E; Flick, B; Frericks, M; Hastings, C; Honarvar, N; Van Cott, A; van Ravenzwaay, B, 2018) | 2.18 |
Afidopyropen was not toxic to adult Hippodamia convergens or adult Orius insidiosus. It was only moderately toxic to Aphelinus certus.
| Excerpt | Reference | Relevance |
|---|---|---|
| " The data of residue amounts of afidopyropen and its metabolite M440I007 in cotton matrix and the environment soil are important to evaluate the safe use of the target compound and establish maximum residue limit (MRL)." | ( Dissipation and safety evaluation of afidopyropen and its metabolite residues in supervised cotton field. Hou, X; Liu, D; Qiao, T; Zhao, Y, 2019) | 1.07 |
| " glycines, afidopyropen was not toxic to adult or third instar Hippodamia convergens (Coleoptera: Coccinellidae) or adult Orius insidiosus (Hemiptera: Anthocoridae), and was only moderately toxic to Aphelinus certus (Hymenoptera: Aphelinidae)." | ( Efficacy of afidopyropen against soybean aphid (Hemiptera: Aphididae) and toxicity to natural enemies. Aita, RC; da Silva Queiroz, O; Ellers-Kirk, CD; Hodgson, EW; Koch, RL; Nyoike, T; Potter, BD, 2020) | 1.33 |
Mixed residues of afidopyropen and M440I007 at the recommended dosage would not cause health concerns in population. The results showed that the risk of application of afidsopropen with the recommended dosages was acceptable.
| Excerpt | Relevance | Reference |
|---|---|---|
| " Finally, dietary risk assessment indicated that the mixed residues of afidopyropen and M440I007 at the recommended dosage would not cause health concerns in population." | ( Human health safety studies of a new insecticide: Dissipation kinetics and dietary risk assessment of afidopyropen and one of its metabolites in cucumber and nectarine. Dong, F; Ji, M; Liu, X; Wu, X; Xie, J; Xu, J; Zheng, Y, 2019) | 0.96 |
| " The results showed that the risk of application of afidopyropen with the recommended dosage was acceptable." | ( Dissipation and safety evaluation of afidopyropen and its metabolite residues in supervised cotton field. Hou, X; Liu, D; Qiao, T; Zhao, Y, 2019) | 1.04 |
| Role | Description |
|---|---|
| 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. |
| 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. |
| [role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] | |
| Class | Description |
|---|---|
| cyclopropanecarboxylate ester | A carboxylic ester resulting from the formal condensation of the hydroxy group of an alcohol or phenol with the carboxy group of cyclopropanecarboxylic acid or its substituted derivatives. |
| pyridines | Any organonitrogen heterocyclic compound based on a pyridine skeleton and its substituted derivatives. |
| organic heterotetracyclic compound | |
| secondary alcohol | A secondary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has two other carbon atoms attached to it. |
| [compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] | |
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 0 (0.00) | 18.7374 |
| 1990's | 0 (0.00) | 18.2507 |
| 2000's | 0 (0.00) | 29.6817 |
| 2010's | 7 (23.33) | 24.3611 |
| 2020's | 23 (76.67) | 2.80 |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||
According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.
| This Compound (32.83) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 0 (0.00%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 30 (100.00%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||