Pyrethrin

Details

• Internal ID: b9d2d506-12fa-4714-92f4-90d188430249
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Fatty acid esters > Pyrethroids > Pyrethrins
• IUPAC Name: [(1S)-2-methyl-4-oxo-3-[(2E)-penta-2,4-dienyl]cyclopent-2-en-1-yl] (1R,3R)-3-[(E)-3-methoxy-2-methyl-3-oxoprop-1-enyl]-2,2-dimethylcyclopropane-1-carboxylate
• SMILES (Canonical): CC1=C(C(=O)CC1OC(=O)C2C(C2(C)C)C=C(C)C(=O)OC)CC=CC=C
• SMILES (Isomeric): CC1=C(C(=O)C[C@@H]1OC(=O)[C@@H]2[C@H](C2(C)C)/C=C(\C)/C(=O)OC)C/C=C/C=C
• InChI: InChI=1S/C22H28O5/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/h7-9,11,16,18-19H,1,10,12H2,2-6H3/b9-8+,13-11+/t16-,18+,19+/m1/s1
• InChI Key: VJFUPGQZSXIULQ-QYVAASDLSA-N
• Popularity: 10,443 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₈O₅
• Molecular Weight: 372.50 g/mol
• Exact Mass: 372.19367399 g/mol
• Topological Polar Surface Area (TPSA): 69.70 Ų
• XlogP: 4.40
• Atomic LogP (AlogP): 3.71
• H-Bond Acceptor: 5
• H-Bond Donor: 0
• Rotatable Bonds: 7

Synonyms

• Pyretrin II
• (+)-Pyrethronyl (+)-pyrethrate
• ENT 7,543
• Pyrethrolone, chrysanthemum dicarboxlic acid methyl ester ester
• SCHEMBL119631
• Chrysanthemumdicarboxylic acid monomethyl ester pyrethrolone ester
• Pyrethrolone ester of chrsanthemumdicarboxylic acid monomethyl ester
• 121-29-9
• 2-Methyl-4-oxo-3-(penta-2,4-dienyl)cyclopent-2-enyl (1R-(1alphaS*(Z)))(3beta)-3-(3-methoxy-2-methyl-3-oxoprop-1-enyl)-2,2-dimethylcyclopropanecarboxylate
• Cyclopropanecarboxylic acid, 3-((1E)-3-methoxy-2-methyl-3-oxo-1-propenyl)-2,2-dimethyl-, (1S)-2-methyl-4-oxo-3-(2Z)-2,4-pentadienyl-2-cyclopenten-1-yl ester, (1R,3R)-
• Cyclopropanecarboxylic acid, 3-(3-methoxy-2-methyl-3-oxo-1-propenyl)-2,2-dimethyl-, 2-methyl-4-oxo-3-(2,4-pentadienyl)-2-cyclopenten-1-yl ester, (1theta-(1alpha(S(Z)),3beta(E)))-
• Cyclopropanecarboxylic acid, 3-(3-methoxy-2-methyl-3-oxo-1-propenyl)-2,2-dimethyl-, 2-methyl-4-oxo-3-(2,4-pentadienyl)-2-cyclopenten-1-yl ester, (R-(1alpha(S*(Z)),3beta(E)))-
• Pyrethrin II (6CI); (+)-Pyrethronyl (+)-pyrethrate; Biospray S; Pyrethrin 2; Pyrethrum mist
• LS-58517
• [(1S)-2-methyl-4-oxo-3-[(2E)-penta-2,4-dienyl]cyclopent-2-en-1-yl] (1R,3R)-3-[(E)-3-methoxy-2-methyl-3-oxo-prop-1-enyl]-2,2-dimethyl-cyclopropanecarboxylate
• Methyl (2E)-3-(3-{[4-((2E)penta-2,4-dienyl)(1S)-5-methyl-3-oxocyclopent-4-enyl]oxycarbonyl}(1R,3R)-2,2-dimethylcyclopropyl)-2-methylprop-2-enoate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9835	98.35%
Caco-2	+	0.6015	60.15%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7991	79.91%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8713	87.13%
OATP1B3 inhibitior	+	0.8761	87.61%
MATE1 inhibitior	-	0.6800	68.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.9413	94.13%
P-glycoprotein inhibitior	+	0.6137	61.37%
P-glycoprotein substrate	-	0.6030	60.30%
CYP3A4 substrate	+	0.6476	64.76%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9131	91.31%
CYP3A4 inhibition	-	0.8116	81.16%
CYP2C9 inhibition	-	0.8396	83.96%
CYP2C19 inhibition	-	0.6707	67.07%
CYP2D6 inhibition	-	0.9503	95.03%
CYP1A2 inhibition	-	0.8287	82.87%
CYP2C8 inhibition	-	0.6203	62.03%
CYP inhibitory promiscuity	-	0.8855	88.55%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.7176	71.76%
Carcinogenicity (trinary)	Non-required	0.6536	65.36%
Eye corrosion	-	0.9551	95.51%
Eye irritation	-	0.9520	95.20%
Skin irritation	-	0.6553	65.53%
Skin corrosion	-	0.9790	97.90%
Ames mutagenesis	+	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7337	73.37%
Micronuclear	-	0.6000	60.00%
Hepatotoxicity	+	0.5302	53.02%
skin sensitisation	-	0.5405	54.05%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	-	0.5778	57.78%
Mitochondrial toxicity	-	0.7125	71.25%
Nephrotoxicity	+	0.8612	86.12%
Acute Oral Toxicity (c)	II	0.7340	73.40%
Estrogen receptor binding	+	0.6986	69.86%
Androgen receptor binding	+	0.7114	71.14%
Thyroid receptor binding	+	0.6000	60.00%
Glucocorticoid receptor binding	+	0.8638	86.38%
Aromatase binding	+	0.5873	58.73%
PPAR gamma	+	0.5695	56.95%
Honey bee toxicity	+	0.9268	92.68%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.7700	77.00%
Fish aquatic toxicity	+	0.9931	99.31%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.46%	94.45%
CHEMBL4040	P28482	MAP kinase ERK2	96.41%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.94%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.56%	91.11%
CHEMBL340	P08684	Cytochrome P450 3A4	91.61%	91.19%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.72%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.33%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.57%	99.17%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	85.41%	94.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.02%	95.89%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.45%	91.07%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	81.13%	95.71%
CHEMBL2996	Q05655	Protein kinase C delta	80.84%	97.79%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.68%	96.95%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	80.57%	91.24%
CHEMBL2581	P07339	Cathepsin D	80.13%	98.95%

Plants that contains it

• Bupleurum chinense
• Bupleurum falcatum
• Bupleurum scorzonerifolium

Cross-Links

• PubChem: 6433155
• NPASS: NPC39122
• LOTUS: LTS0226509
• wikiData: Q105287236