Allethrin

Details

• Internal ID: 4bee905d-d200-4166-a22e-cfe10a4bbf88
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Fatty acid esters > Pyrethroids
• IUPAC Name: (2-methyl-4-oxo-3-prop-2-enylcyclopent-2-en-1-yl) 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate
• SMILES (Canonical): CC1=C(C(=O)CC1OC(=O)C2C(C2(C)C)C=C(C)C)CC=C
• SMILES (Isomeric): CC1=C(C(=O)CC1OC(=O)C2C(C2(C)C)C=C(C)C)CC=C
• InChI: InChI=1S/C19H26O3/c1-7-8-13-12(4)16(10-15(13)20)22-18(21)17-14(9-11(2)3)19(17,5)6/h7,9,14,16-17H,1,8,10H2,2-6H3
• InChI Key: ZCVAOQKBXKSDMS-UHFFFAOYSA-N
• Popularity: 903 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₆O₃
• Molecular Weight: 302.40 g/mol
• Exact Mass: 302.18819469 g/mol
• Topological Polar Surface Area (TPSA): 43.40 Ų
• XlogP: 4.80
• Atomic LogP (AlogP): 4.00
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 5

Synonyms

• D-trans Allethrin
• d-cis,trans-Allethrin
• d-cis-trans-Allethrin
• Allyl cinerin
• Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-, 2-methyl-4-oxo-3-(2-propenyl)-2-cyclopenten-1-yl ester, (1-alpha(S*),3-beta)-(+-)-
• Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-, (1R)-2-methyl-4-oxo-3-(2-propenyl)-2-cyclopenten-1-yl ester. (1S.3S)-rel-
• Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-, (1R)-2-methyl-4-oxo-3-(2-propenyl)-2-cyclopenten-1-yl ester, (1S,3S)-rel-
• HSDB 1511
• PYNAMIN (JAPAN)
• RefChem:554622
• PALLETHRINE (FRANCE)
• Pesticide Code: 004001
• OMS 468
• (RS)-Allethronyl (1R, cis)-chrysanthemate /d-cis-Allethrin/
• (S)-Allethronyl (1R, trans)-chrysanthemate /S-Bioallethrin/
• (RS)-Allethronyl (1R, cis, trans)-chrysanthemate /d-Allethrin/
• (S)-Allethronyl (1R, cis, trans)-chrysanthemate /GZ1925000/
• (RS)-Allethronyl (1R, trans) chrysanthemate /d-trans-Allethrin/ /Esbiothrin/
• (RS)-3-Allyl-2-methyl-4-oxocyclopent-2-enyl (1RS, cis, trans)-2,2-dimethyl-3-(2,2-dimethylvinyl)cyclopropane-carboxylate /Allethrin/ /d-Allethrin/ /d-cis-Allethrin/ /d-trans-Allethrin/ /Esbiothrin/ /S-Bioallethrin/
• 2-Methyl-4-oxo-3-(2-propenyl)-2-cyclo-penten-1-yl 2,2-dimethyl 3-(2-methyl-1-propenyl) cyclopropanecarboxylate /Allethrin/ /d-Allethrin/ /d-cis-Allethrin/ /d-trans-Allethrin/ /Esbiothrin/ /S-Bioallethrin/
• d-trans-Chrysanthemum monocarboxylic acid ester of d-2-allyl-4-hydroxy-3-methyl-2-cyclopenten-1-one /S-Bioallethrin/
• ALLETHRIN
• 584-79-2
• Esbiothrin
• Pynamin
• 84030-86-4
• D-Allethrin
• 22431-63-6
• alpha-dl-trans-Allethrin
• Pallethrine
• Allethrine
• Pyresin
• Pyresyn
• Allyl cinerin I
• Necarboxylic acid
• D-TRANS-ALLETHRIN
• MFCD00045443
• (2-methyl-4-oxo-3-prop-2-enylcyclopent-2-en-1-yl) 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate
• Bioaletrina
• Cinerin I allyl homolog
• 42534-61-2
• 3-Allyl-2-methyl-4-oxo-2-cyclopenten-1-yl chrysanthemate
• 3972-20-1
• DTXSID8035180
• CHEBI:34572
• trans-chrysanthemummonocarboxylate
• Allyl homolog of cinerin I
• Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-, 2-methyl-4-oxo-3-(2-propenyl)-2-cyclopenten-1-yl ester
• FMC 249
• NCGC00163953-03
• NIA 249
• FDA 1446
• 28434-00-6
• (1R)-2,2-Dimethyl-3-(2-methyl-1-propen-1-yl)cyclopropanecarboxylicacid 2-methyl-4-oxo-3-(2-propen-1-yl)-2-cyclopenten-1-ylester
• (3-allyl-2-methyl-4-oxo-cyclopent-2-en-1-yl) 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylate
• (+)-Allelrethonyl (+)-cis,trans-chrysanthemate
• 3-Allyl-4-keto-2-methylcyclopentenyl chrysanthemum monocarboxylate
• Allethrolone ester of chrysanthemummonocarboxylic acid
• Bioallethrin (BAN)
• 3-allyl-2-methyl-4-oxocyclopent-2-en-1-yl 2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropanecarboxylate
• 28057-48-9
• (+/-)-Allerethonyl (+/-)-cis,trans-chrysanthemate
• 0X03II877M
• (+)-trans-Bioallethrin
• ALLETHRIN [HSDB]
• ALLETHRIN I [MI]
• Duocide [veterinary] (TN)
• SCHEMBL26963
• orb1305382
• CHEMBL1872535
• DTXCID6015180
• D,L-chrysanthemum monocarboxylate
• [(1S)-2-methyl-4-oxo-3-prop-2-enylcyclopent-2-en-1-yl] (1R,3R)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate
• HY-B1559
• MSK20484
• NSC11782
• Tox21_400074
• D-allethrolone d-trans-chrysanthemate
• ENT 16275
• ENT 17510
• AKOS015900219
• NCGC00163953-01
• NCGC00163953-02
• NCGC00163953-04
• NCGC00164471-01
• AS-11751
• CAS-584-79-2
• Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-, 2-methyl-4-oxo-3-(2-propenyl)-2-cyclopenten-1-yl ester, [1R-[1.alpha.(S*),3.beta.]]-
• DB-047389
• ()-Allerethonyl ()-cis,trans-chrysanthemate
• CS-0013441
• NS00008969
• Allethrin, PESTANAL(R), analytical standard
• Esbiothrin, PESTANAL(R), analytical standard
• D07530
• Bioallethrin, PESTANAL(R), analytical standard
• 584A792
• Q1851694
• (.+-.)-Allelrethonyl (.+-.)-cis,trans-chrysanthemate
• (+)-trans-Chrysanthemumic acid ester of (.+-.)-allethrolone
• WLN: L5V BUTJ B2U1 C1 DOV- BL3TJ A1 A1 C1UY1&1
• 2-Allyl-4-hydroxy-3-methyl-2-cyclopenten-1-one ester of 2,2-dimethyl-3-(2-methyl propenyl) cyclopropane carboxylic acid
• 2-methyl-4-oxo-3-(prop-2-en-1-yl)cyclopent-2-en-1-yl 2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropanecarboxylate
• 3-Allyl-2-methyl-4-oxo-2-cyclopenten-1-yl 2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate, (1R-(1.alpha.(S*),3.beta.))-
• Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methylpropenyl)-, ester with 2-allyl-4-hydroxy-3-methyl-2-cyclopenten-1-one
• Cyclopropanecarboxylic acid,2-dimethyl-3-(2-methyl-1-propenyl)-, 2-methyl-4-oxo-3-(2-propenyl)-2-cyclopenten-1-yl ester (VA
• Cyclopropanecarboxylic acid,2-dimethyl-3-(2-methyl-1-propenyl)-, 2-methyl-4-oxo-3-(2-propenyl)-2-cyclopenten-1-yl ester, d-trans-
• Cyclopropanecarboxylic acid,2-dimethyl-3-(2-methyl-1-propenyl)-, 2-methyl-4-oxo-3-(2-propenyl)-2-cyclopentene-1-yl ester
• Cyclopropanecarboxylic acid,2-dimethyl-3-(2-methylpropenyl)-, ester with 2-allyl-4-hydroxy-3-methyl-2-cyclopenten-1-one
• D-trans-Allethrin, (S)-3-Allyl-2-methyl-4-oxocyclopent-2-enyl-(1R,3R)-2,2-dimethyl-3-(2-methyl-prop-1-enyl)cyclopropancarboxylate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9917	99.17%
Caco-2	+	0.6889	68.89%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.8205	82.05%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8894	88.94%
OATP1B3 inhibitior	+	0.8585	85.85%
MATE1 inhibitior	+	0.6400	64.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.5513	55.13%
P-glycoprotein inhibitior	-	0.5555	55.55%
P-glycoprotein substrate	-	0.7646	76.46%
CYP3A4 substrate	+	0.6032	60.32%
CYP2C9 substrate	-	0.8058	80.58%
CYP2D6 substrate	-	0.9107	91.07%
CYP3A4 inhibition	-	0.8137	81.37%
CYP2C9 inhibition	-	0.8178	81.78%
CYP2C19 inhibition	-	0.5419	54.19%
CYP2D6 inhibition	-	0.9481	94.81%
CYP1A2 inhibition	-	0.8106	81.06%
CYP2C8 inhibition	-	0.7170	71.70%
CYP inhibitory promiscuity	-	0.8294	82.94%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.7450	74.50%
Carcinogenicity (trinary)	Non-required	0.5709	57.09%
Eye corrosion	-	0.9375	93.75%
Eye irritation	-	0.7773	77.73%
Skin irritation	-	0.5734	57.34%
Skin corrosion	-	0.9660	96.60%
Ames mutagenesis	+	0.8800	88.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5941	59.41%
Micronuclear	-	0.6200	62.00%
Hepatotoxicity	+	0.5408	54.08%
skin sensitisation	+	0.6771	67.71%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	-	0.6556	65.56%
Mitochondrial toxicity	-	0.7875	78.75%
Nephrotoxicity	+	0.7731	77.31%
Acute Oral Toxicity (c)	II	0.7479	74.79%
Estrogen receptor binding	-	0.5741	57.41%
Androgen receptor binding	+	0.7991	79.91%
Thyroid receptor binding	+	0.5449	54.49%
Glucocorticoid receptor binding	-	0.5324	53.24%
Aromatase binding	+	0.5234	52.34%
PPAR gamma	-	0.5441	54.41%
Honey bee toxicity	+	0.9768	97.68%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.8000	80.00%
Fish aquatic toxicity	+	0.9958	99.58%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.61%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.10%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.82%	91.11%
CHEMBL340	P08684	Cytochrome P450 3A4	90.50%	91.19%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.77%	85.14%
CHEMBL2581	P07339	Cathepsin D	86.58%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.13%	95.56%
CHEMBL1902	P62942	FK506-binding protein 1A	85.36%	97.05%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.08%	96.95%
CHEMBL2996	Q05655	Protein kinase C delta	84.45%	97.79%
CHEMBL4040	P28482	MAP kinase ERK2	83.88%	83.82%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.35%	86.33%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.67%	91.07%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.29%	99.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.02%	95.89%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.24%	93.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.13%	94.33%

Plants that contains it

• Tanacetum cinerariifolium

Cross-Links

• PubChem: 11442
• NPASS: NPC253749
• LOTUS: LTS0078279
• wikiData: Q1851694