Pyrethrin I

Details

• Internal ID: 440e2c6d-7e1b-476c-a98a-d7f8cf82f5c7
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Fatty acid esters > Pyrethroids > Pyrethrins
• IUPAC Name: cis-[(1S)-2-methyl-4-oxo-3-[(2Z)-penta-2,4-dienyl]cyclopent-2-en-1-yl] (1R,3R)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate
• InChI: InChI=1S/C21H28O3/c1-7-8-9-10-15-14(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/b9-8-/t16-,18+,19+/m1/s1
• InChI Key: ROVGZAWFACYCSP-VUMXUWRFSA-N
• Popularity: 402 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₈O₃
• Molecular Weight: 328.40 g/mol
• Exact Mass: 328.20384475 g/mol
• Topological Polar Surface Area (TPSA): 43.40 Ų
• XlogP: 5.40
• Atomic LogP (AlogP): 4.56
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 6

Synonyms

• 121-21-1
• Chrysanthemum monocarboxylic acid pyrethrolone ester
• T018I9EQOL
• Piretrina 1
• [(1S)-2-methyl-4-oxo-3-[(2Z)-penta-2,4-dienyl]cyclopent-2-en-1-yl] (1R,3R)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate
• Pyrethrine I
• (1S)-2-methyl-4-oxo-3-[(2Z)-penta-2,4-dien-1-yl]cyclopent-2-en-1-yl (1R,3R)-2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropanecarboxylate
• (+)-Pyrethronyl (+)-trans-chrysanthemate
• Caswell No. 715
• Pyrethrolone, chrysanthemum monocarboxylic acid ester
• Piretrina 1 [Portuguese]
• Pyrethrin I [BSI:ISO]
• UNII-T018I9EQOL
• Pyrethrine I [ISO-French]
• HSDB 6302
• Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-, (1S)-2-methyl-4-oxo-3-(2Z)-2,4-pentadienyl-2-cyclopenten-1-yl ester, (1R,3R)-
• EINECS 204-455-8
• Bubil (TN)
• EPA Pesticide Chemical Code 069001
• BRN 2004306
• PYRETHRIN I [MI]
• PYRETHRIN I [ISO]
• PYRETHRIN I [HSDB]
• SCHEMBL26537
• 3-09-00-00215 (Beilstein Handbook Reference)
• PYRETHRIN I [WHO-DD]
• DTXSID4034499
• CHEBI:27815
• Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methylpropenyl)-, ester with 4-hydroxy-3-methyl-2-(2,4-pentadienyl)-2-cyclopenten-1-one
• 1ST20457
• 2,2-Dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylic acid 2-methyl-4-oxo-3-(2,4-pentadienyl)-2-cycloenten-1-yl ester
• 2-Methyl-4-oxo-3-(2,4-pentadienyl)-2-cyclopenten-2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropane carboxylate
• Cyclopropaneacrylic acid, 2,2-dimethyl-3-(2-methylpropenyl)-, ester with 4-hydroxy-3-methyl-2-(2,4-pentadienyl)-2-cyclopenten-1-one
• Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-, 2-methyl-4-oxo-3-(2,4-pentadienyl)-2-cyclopenten-1-yl ester, (1R-(1alpha(S*(Z)),3beta))-
• Pyrethrin 1 100 microg/mL in Cyclohexane
• C07594
• D08452
• Q7263468
• (1S)-2-METHYL-4-OXO-3-(2Z)-2,4-PENTADIENYLCYCLOPENTEN-1-YL (1R,3R)-2,2-DIMETHYL-3-(2-METHYL-1-PROPENYL)CYCLOPROPANECARBOXYLATE
• (Z)-(S)-2-METHYL-4-OXO-3-(PENTA-2,4-DIENYL)CYCLOPENT-2-ENYL (+)-TRANS-CHRYSANTHEMATE
• (Z)-(S)-2-METHYL-4-OXO-3-(PENTA-2,4-DIENYL)CYCLOPENT-2-ENYL (1R,3R)-2,2-DIMETHYL-3-(2-METHYLPROP-1-ENYL)CYCLOPROPANECARBOXYLATE
• [(1S)-2-methyl-4-oxo-3-[(2Z)-penta-2,4-dienyl]cyclopent-2-en-1-yl] (1R,3R)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylate
• 2-Methyl-4-oxo-3-(penta-2,4-dienyl)cyclopent-2-enyl (1R-(1alpha(S*(Z)),3beta))-chrysanthemate
• Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-, 2-methyl-4-oxo-3-(2,4-pentadienyl)-2-cyclopenten-1-yl ester, (1theta-(1alpha(S(Z)),3beta))-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9917	99.17%
Caco-2	+	0.7225	72.25%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.8205	82.05%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8732	87.32%
OATP1B3 inhibitior	+	0.8585	85.85%
MATE1 inhibitior	-	0.6800	68.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.8736	87.36%
P-glycoprotein inhibitior	-	0.4921	49.21%
P-glycoprotein substrate	-	0.7014	70.14%
CYP3A4 substrate	+	0.6348	63.48%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9131	91.31%
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	-	0.7059	70.59%
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	-	0.9270	92.70%
Skin irritation	-	0.5734	57.34%
Skin corrosion	-	0.9660	96.60%
Ames mutagenesis	+	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6849	68.49%
Micronuclear	-	0.6200	62.00%
Hepatotoxicity	-	0.5500	55.00%
skin sensitisation	+	0.6771	67.71%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	-	0.6556	65.56%
Mitochondrial toxicity	-	0.7875	78.75%
Nephrotoxicity	+	0.7518	75.18%
Acute Oral Toxicity (c)	II	0.7479	74.79%
Estrogen receptor binding	+	0.6663	66.63%
Androgen receptor binding	+	0.7927	79.27%
Thyroid receptor binding	+	0.5275	52.75%
Glucocorticoid receptor binding	+	0.7910	79.10%
Aromatase binding	+	0.6208	62.08%
PPAR gamma	+	0.5985	59.85%
Honey bee toxicity	+	0.9768	97.68%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.7500	75.00%
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
CHEMBL4040	P28482	MAP kinase ERK2	96.58%	83.82%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.58%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.45%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.75%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.66%	85.14%
CHEMBL340	P08684	Cytochrome P450 3A4	89.56%	91.19%
CHEMBL2996	Q05655	Protein kinase C delta	85.79%	97.79%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.78%	95.56%
CHEMBL2581	P07339	Cathepsin D	84.00%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.00%	99.17%
CHEMBL1902	P62942	FK506-binding protein 1A	83.79%	97.05%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.50%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.98%	95.89%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	81.89%	96.95%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.23%	94.33%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	80.99%	100.00%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	80.91%	95.71%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	80.34%	91.71%

Plants that contains it

• Tanacetum coccineum

Cross-Links

• PubChem: 5281045
• LOTUS: LTS0175508
• wikiData: Q7263468