Pyrethrins
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Basic Info
| Common Name | Pyrethrins(F05996) |
| 2D Structure | |
| FRCD ID | F05996 |
| CAS Number | 8003-34-7 |
| PubChem CID | 71310221 |
| Formula | C43H56O8 |
| IUPAC Name | [(1S)-2-methyl-4-oxo-3-[(2E)-penta-2,4-dienyl]cyclopent-2-en-1-yl] (1R)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate;[2-methyl-4-oxo-3-[(2E)-penta-2,4-dienyl]cyclopent-2-en-1-yl] (1R)-3-[(E)-3-methoxy-2-methyl-3-oxoprop-1-enyl]-2,2-dimethylcyclopropane-1-carboxylate |
| InChI Key | VXSIXFKKSNGRRO-YWUDCVDHSA-N |
| InChI | InChI=1S/C22H28O5.C21H28O3/c1-7-8-9-10-15-14(3)18(12-17(15)23)27-21(25)19-16(22(19,4)5)11-13(2)20(24)26-6;1-7-8-9-10-15-14(4)18(12-17(15)22)24-20(23)19-16(11-13(2)3)21(19,5)6/h7-9,11,16,18-19H,1,10,12H2,2-6H3;7-9,11,16,18-19H,1,10,12H2,2-6H3/b9-8+,13-11+;9-8+/t16?,18?,19-;16?,18-,19-/m00/s1 |
| Canonical SMILES | CC1=C(C(=O)CC1OC(=O)C2C(C2(C)C)C=C(C)C)CC=CC=C.CC1=C(C(=O)CC1OC(=O)C2C(C2(C)C)C=C(C)C(=O)OC)CC=CC=C |
| Isomeric SMILES | CC1=C(C(=O)C[C@@H]1OC(=O)[C@@H]2C(C2(C)C)C=C(C)C)C/C=C/C=C.CC1=C(C(=O)CC1OC(=O)[C@@H]2C(C2(C)C)/C=C(\C)/C(=O)OC)C/C=C/C=C |
| Synonyms |
[(1S)-2-methyl-4-oxo-3-[(2E)-penta-2,4-dienyl]cyclopent-2-en-1-yl] (1R)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate;[2-methyl-4-oxo-3-[(2E)-penta-2,4-dienyl]cyclopent-2-en-1-yl] (1R
SC-57935
Pyrethrum extract, >=50% (sum of pyrethrines)
6644AF
C22H28O5.C21H28O3
Pyrethrins
Pyrethrum extract
8003-34-7
Pyrethrins (technical)
VXSIXFKKSNGRRO-YWUDCVDHSA-N
|
| Classifies |
Pollutant
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Lipids and lipid-like molecules |
| Class | Fatty Acyls |
| Subclass | Fatty acid esters |
| Intermediate Tree Nodes | Pyrethroids |
| Direct Parent | Pyrethrins |
| Alternative Parents | |
| Molecular Framework | Not available |
| Substituents | Pyrethrin-backbone - Monocyclic monoterpenoid - Monoterpenoid - Carbocyclic fatty acid - Cyclopropanecarboxylic acid or derivatives - Dicarboxylic acid or derivatives - Alpha,beta-unsaturated carboxylic ester - Enoate ester - Methyl ester - Carboxylic acid ester - Ketone - Cyclic ketone - Carboxylic acid derivative - Hydrocarbon derivative - Organic oxide - Organic oxygen compound - Carbonyl group - Organooxygen compound - Aliphatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as pyrethrins. These are pyrethroids with a structure based on a skeleton that is characterized by the presence of a chrysanthemic acid esterified with a cyclopentenone derivative. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 700.913 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 8 |
| Rotatable Bond Count | 16 |
| Complexity | 1390 |
| Monoisotopic Mass | 700.398 |
| Exact Mass | 700.398 |
| Formal Charge | 0 |
| Heavy Atom Count | 51 |
| Defined Atom Stereocenter Count | 3 |
| Undefined Atom Stereocenter Count | 3 |
| Defined Bond Stereocenter Count | 3 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 2 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.8846 |
| Human Intestinal Absorption | HIA+ | 0.9010 |
| Caco-2 Permeability | Caco2+ | 0.5492 |
| P-glycoprotein Substrate | Substrate | 0.5154 |
| P-glycoprotein Inhibitor | Inhibitor | 0.7876 |
| Non-inhibitor | 0.6994 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8616 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.7991 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8980 |
| CYP450 2D6 Substrate | Non-substrate | 0.8871 |
| CYP450 3A4 Substrate | Substrate | 0.6428 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.8287 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.8396 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9503 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.6707 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8116 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.8855 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9581 |
| Non-inhibitor | 0.9608 | |
| AMES Toxicity | AMES toxic | 0.8680 |
| Carcinogens | Non-carcinogens | 0.7699 |
| Fish Toxicity | High FHMT | 0.9929 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9709 |
| Honey Bee Toxicity | High HBT | 0.8998 |
| Biodegradation | Not ready biodegradable | 0.8675 |
| Acute Oral Toxicity | II | 0.7340 |
| Carcinogenicity (Three-class) | Non-required | 0.6536 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.6917 | LogS |
| Caco-2 Permeability | 0.7610 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 3.2385 | LD50, mol/kg |
| Fish Toxicity | 0.0443 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.9980 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Pumpkin seeds (Watermelon seeds, Other seeds of species of familia Cucurbitaceae, not elsewhere mentioned,) | 0401100 | European Union | 3 | 01/09/2008 | |
| Borage seeds (Corn gromwell seeds, Evening primrose seeds, Honesty seeds, Honesty seeds, Perilla seeds, Purple viper's bugloss seeds,) | 0401120 | European Union | 3 | 01/09/2008 | |
| Buckwheat and other pseudocereals (Amaranth/kiwicha, Amaranth/kiwicha, Amaranth/kiwicha, Kaniwa/canihua, Quinoa, Chia seeds,) | 0500020 | European Union | 3 | 01/09/2008 | |
| Pine nut kernels (Pine nut kernels from other species than Pinus pinea, Pine nut kernels from other species than Pinus pinea, Pine nut kernels from other species than Pinus pinea, Pine nut kernels ... | 0120090 | European Union | 1 | 01/09/2008 | |
| (d) any other parts of the plant (Blond psyllium (seeds, husks), Chamomile (seeds), Cherries (sweet) (stems), China/Jesuit's bark (bark), China/Jesuit's bark (bark), Cocoa (husks), Condurango (bark... | 0639000 | European Union | 0.5 | 01/09/2008 | |
| (b) bovine (American buffalo, Banteng, Buffalo, European buffalo/wisent, Gayal, Yak (domestic), Zebu, Hybrids of genera Bison, Bos, Bubalus and Poëphagus,) | 1012000 | European Union | 0.05* | 01/09/2008 | |
| Celery | Japan | 1ppm | |||
| Parsley | Japan | 1ppm | |||
| Parsnip | Japan | 1ppm | |||
| Carrot | Japan | 1ppm | |||
| Cabbage | Korea | 1ppm | |||
| Citru | Korea | 1ppm | |||
| American persimmons/Virginia kaki (Black sapotes, Green sapotes, White sapotes, Yellow sapotes/canistels,) | 0162060 | European Union | 1 | 01/09/2008 | |
| Mandarins (Calamondins, Clementines, Cleopatra mandarins, Minneolas, Satsumas/clausellinas, Tangerines/dancy mandarins, Tangors, Other hybrids of Citrus reticulata, not elsewhere mentioned,) | 0110050 | European Union | 1 | 01/09/2008 | |
| Passionfruits/maracujas (Banana passionfruits, Giant granadillas, Granadillas, Monstera fruits, Wingedstem passionflower fruits,) | 0162030 | European Union | 1 | 01/09/2008 | |
| Blueberries (Aronia berries/chokeberries (black, purple and red), Aronia berries/chokeberries (black, purple and red), Aronia berries/chokeberries (black, purple and red), Bearberries, Bilberries/E... | 0154010 | European Union | 1 | 01/09/2008 | |
| Mulberries (black and white) | 0154060 | European Union | 1 | 01/09/2008 | |
| Prickly pears/cactus fruits (Pitayas/dragon fruits, Red pitayas, Saguaro fruits, Yellow pitayas,) | 0162040 | European Union | 1 | 01/09/2008 | |
| Elderberries (Bayberries, Buffalo berries, Che berries, Dwarf elderberries, Guelder rose berries, Hawberries, Midland hawberries, Phalsa fruits, Riberries, Rowan berries, Saskatoons/saskatoons berr... | 0154080 | European Union | 1 | 01/09/2008 | |
| Jambuls/jambolans (Acerolas/Barbados cherries, Arbutus berries, Camu camus, Carandas, Coco plums, Grumichamas/Brazil cherries, Hog plums/yellow mombins, Java apples, Otaheite gooseberries, Sea grap... | 0161070 | European Union | 1 | 01/09/2008 |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Current Research on the Safety of Pyrethroids Used as Insecticides. | Medicina (Kaunas) | 2018 Aug 28 | 30344292 |
| Augmentation of pyrethrins content in callus of Chrysanthemum cinerariaefoliumand establishing its insecticidal activity by molecular docking of NavMS SodiumChannel Pore receptor. | 3 Biotech | 2018 Aug | 30105192 |
| Occurrence and Health Risk of Patulin and Pyrethroids in Fruit Juices Consumed in Bangkok, Thailand. | J Food Prot | 2017 Sep | 28762777 |
| Comparison of subacute effects of two types of pyrethroid insecticides using metabolomics methods. | Pestic Biochem Physiol | 2017 Nov | 29183587 |
| Effect of pyrethroid treatment against sea lice in salmon farming regarding consumers' health. | Food Chem Toxicol | 2017 Jul | 28458010 |
| The implication of p66shc in oxidative stress induced by deltamethrin. | Chem Biol Interact | 2017 Dec 25 | 28987327 |
| Can fractal methods applied to video tracking detect the effects of deltamethrin pesticide or mercury on the locomotion behavior of shrimps? | Ecotoxicol Environ Saf | 2017 Aug | 28419951 |
| Olive phenolic compounds attenuate deltamethrin-induced liver and kidney toxicity through regulating oxidative stress, inflammation and apoptosis. | Food Chem Toxicol | 2017 Aug | 28595958 |
| Molecular Markers for Pyrethrin Autoxidation in Stored Pyrethrum Crop: Analysisand Structure Determination. | J Agric Food Chem | 2016 Sep 28 | 27599033 |
| Evaluation and physiological correlation of plasma proteomic fingerprints for deltamethrin-induced hepatotoxicity in Wistar rats. | Life Sci | 2016 Sep 1 | 27142831 |
| Management of Head Louse Infestations in the United States-A Literature Review. | Pediatr Dermatol | 2016 Sep | 27595869 |
| Curcumin modulates oxidative stress and genotoxicity induced by a type II fluorinated pyrethroid, beta-cyfluthrin. | Food Chem Toxicol | 2016 Nov | 27623179 |
| Suspected poisoning of domestic animals by pesticides. | Sci Total Environ | 2016 Jan 1 | 26367188 |
| Deciphering the groove binding modes of tau-fluvalinate and flumethrin with calf thymus DNA. | Spectrochim Acta A Mol Biomol Spectrosc | 2016 Feb 15 | 26571092 |
| Oxidative damage and hepatotoxicity associated with deltamethrin in rats: The protective effects of Amaranthus spinosus seed extract. | Biomed Pharmacother | 2016 Dec | 27728895 |
| Distribution, Metabolism and Toxic Effects of Beta-Cypermethrin in Lizards (Eremias argus) Following Oral Administration. | J Hazard Mater | 2016 Apr 5 | 26698673 |
| Co-Metabolic Degradation of β-Cypermethrin and 3-Phenoxybenzoic Acid by Co-Culture of Bacillus licheniformis B-1 and Aspergillus oryzae M-4. | PLoS One | 2016 | 27898684 |
| Characteristics of suspended solids affect bifenthrin toxicity to the calanoid copepods Eurytemora affinis and Pseudodiaptomus forbesi. | Environ Toxicol Chem | 2015 Oct | 25939857 |
| Pharmacodynamic interaction of Spirulina platensis and deltamethrin in freshwater fish Nile tilapia, Oreochromis niloticus: impact on lipid peroxidation and oxidative stress. | Environ Sci Pollut Res Int | 2015 Feb | 25231739 |
| A comparison of the sublethal and lethal toxicity of four pesticides in Hyalella azteca and Chironomus dilutus. | Environ Sci Pollut Res Int | 2015 Aug | 25804662 |