Cinerin I

Details

• Internal ID: 8e3057b7-dc24-487a-a105-5b94a06f2ad1
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Fatty acid esters > Pyrethroids
• IUPAC Name: [(1S)-3-[(Z)-but-2-enyl]-2-methyl-4-oxocyclopent-2-en-1-yl] (1R,3R)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate
• SMILES (Canonical): CC=CCC1=C(C(CC1=O)OC(=O)C2C(C2(C)C)C=C(C)C)C
• SMILES (Isomeric): C/C=C\CC1=C([C@H](CC1=O)OC(=O)[C@@H]2[C@H](C2(C)C)C=C(C)C)C
• InChI: InChI=1S/C20H28O3/c1-7-8-9-14-13(4)17(11-16(14)21)23-19(22)18-15(10-12(2)3)20(18,5)6/h7-8,10,15,17-18H,9,11H2,1-6H3/b8-7-/t15-,17+,18+/m1/s1
• InChI Key: FMTFEIJHMMQUJI-DFKXKMKHSA-N
• Popularity: 19 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₈O₃
• Molecular Weight: 316.40 g/mol
• Exact Mass: 316.20384475 g/mol
• Topological Polar Surface Area (TPSA): 43.40 Ų
• XlogP: 5.00
• Atomic LogP (AlogP): 4.39
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 5

Synonyms

• 25402-06-6
• Cinerin
• Cinerine I
• CINERIN 1
• Cinerin I [BSI:ISO]
• UNII-3LA34LQ1VC
• Cinerine I [ISO-French]
• 3LA34LQ1VC
• HSDB 6837
• CINERIN I [ISO]
• EINECS 246-948-0
• CINERIN I [MI]
• [(1S)-3-[(Z)-but-2-enyl]-2-methyl-4-oxocyclopent-2-en-1-yl] (1R,3R)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate
• CHEBI:3706
• 97-12-1
• DTXSID4041787
• Chrysanthemummonocarboxylic acid, cinerolone ester
• Cinerolone, chrysanthemummonocarboxylic acid ester
• 3-(2-butenyl)-2-methyl-4-oxo-2-cyclopenten-1-yl 2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopentanecarboxylate
• Cinerine I (ISO-French)
• Chrysanthemummonocarboxilic acid, 3-(2-butenyl)-2-methyl-4-oxo-2-cyclopenten-1-yl ester
• (1S)-3-[(2Z)-but-2-en-1-yl]-2-methyl-4-oxocyclopent-2-en-1-yl (1R,3R)-2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropanecarboxylate
• 2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylic acid 3-(2-butenyl)-2-methyl-4-oxo-2-cyclopenten-1-yl ester
• 3-(2-Butenyl)-2-methyl-4-oxo-2-cyclopenten-1-yl 2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate (1R-(1alpha(S*(Z)),3beta))-
• Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-, (1S)-3-(2Z)-2-butenyl-2-methyl-4-oxo-2-cyclopenten-1-yl ester, (1R,3R)-
• (Z)-(S)-3-(BUT-2-ENYL)-2-METHYL-4-OXOCYCLOPENT-2-ENYL (+)-TRANS-CHRYSANTHEMATE
• (1S)-3-(2Z)-2-BUTENYL-2-METHYL-4-OXO-2-CYCLOPENTEN-1-YL (1R,3R)-2,2-DIMETHYL-3-(2-METHYL-1-PROPENYL)CYCLOPROPANECARBOXYLATE
• (Z)-(S)-3-(BUT-2-ENYL)-2-METHYL-4-OXOCYCLOPENT-2-ENYL (1R,3R)-2,2-DIMETHYL-3-(2-METHYLPROP-1-ENYL)CYCLOPROPANECARBOXYLATE
• Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-, 3-(2-butenyl)-2-methyl-4-oxo-2-cyclopenten-1-yl ester, (1R-(1alpha(S*(Z)),3beta))-
• Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methylpropenyl)-, ester with 2-(2-butenyl)-4-hydroxy-3-methyl-2-cyclopenten-1-one
• ((1S)-3-((Z)-but-2-enyl)-2-methyl-4-oxocyclopent-2-en-1-yl) (1R,3R)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate
• (1R)-3-((2Z)-but-2-en-1-yl)-2-methyl-4-oxocyclopent-2-en-1-yl (1R,3R)-2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropane-1-carboxylate
• (1R)-3-[(2Z)-BUT-2-EN-1-YL]-2-METHYL-4-OXOCYCLOPENT-2-EN-1-YL (1R,3R)-2,2-DIMETHYL-3-(2-METHYLPROP-1-EN-1-YL)CYCLOPROPANE-1-CARBOXYLATE
• (1S)-3-((2Z)-but-2-en-1-yl)-2-methyl-4-oxocyclopent-2-en-1-yl (1R,3R)-2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropanecarboxylate
• (1S)-3-((2Z)-But-2-en-1-yl)-2-methyl-4-oxocyclopent-2-en-1-yl (1R,3S)-2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropane-1-carboxylic acid
• (1S)-3-[(2Z)-But-2-en-1-yl]-2-methyl-4-oxocyclopent-2-en-1-yl (1R,3S)-2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropane-1-carboxylic acid
• Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-, 3-(2-butenyl)-2-methyl-4-oxo-2-cyclopenten-1-yl ester, [1R-[1.alpha.[S*(Z)],3.beta.]]-
• Pyrethrin (cinerin I)
• RefChem:126224
• Pesticide Code: 069009
• DTXCID2021787
• 3-[2-Butenyl]-2-methyl-4-oxo-2-cyclopenten-1-yl 2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate, (1R-(1.alpha.(S*(Z)),3.beta.))-
• 2,2-Dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylic acid 3-(2-butyl)-2-methyl-4-oxo-2-cyclopenten-1-yl-ester
• Chrysanthemummonocarboxilic acid, 3(2butenyl)2methyl4oxo2cyclopenten1yl ester
• (1R,3R)-2,2-Dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylic acid (1S)-3-(2Z)-(2-butenyl)-2-methyl-4-oxo-2-cyclopenten-1-yl-ester
• 2,2Dimethyl3(2methyl1propenyl)cyclopropanecarboxylic acid 3(2butenyl) 2methyl4oxo2cyclopenten1ylester
• 246-948-0
• 3(2Butenyl)2methyl4oxo2cyclopenten1yl 2,2dimethyl3(2methyl1propenyl)cyclopropanecarboxylate (1R(1alpha(S*(Z)),3beta))
• 3-(2-Butenyl)-2-methyl-4-oxo-2-cyclopenten-1-yl 2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate, (1R-(1alpha(S*(Z)),3beta))-
• FMTFEIJHMMQUJI-FPLPWBNLSA-N
• [3-[(E)-but-2-enyl]-2-methyl-4-oxocyclopent-2-en-1-yl] 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate
• Cyclopropanecarboxylicacid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-,(1S)-3-(2Z)-2-butenyl-2-methyl-4-oxo-2-cyclopenten-1-yl ester, (1R,3R)-
• cinerin-1
• 3-(But-2-enyl)-2-methyl-4-oxocyclopent-2-enyl 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylate
• SCHEMBL118717
• FMTFEIJHMMQUJI-DFKXKMKHSA-N
• FC20443
• (1S)-3-[(2Z)-but-2-en-1-yl]-2-methyl-4-oxocyclopent-2-en-1-yl (1R,3R)-2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropane-1-carboxylate
• 2,2-Dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylic acid 3-(2-butyl)- 2-methyl-4-oxo-2-cyclopenten-1-yl-ester
• C09845
• Q27106172
• (1R,3R)-2,2-Dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylic acid (1S)-3-(2Z)-2-butenyl-2-methyl-4-oxo-2-cyclopenten-1-yl este r

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9932	99.32%
Caco-2	+	0.7138	71.38%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.8473	84.73%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8741	87.41%
OATP1B3 inhibitior	+	0.8984	89.84%
MATE1 inhibitior	-	0.6800	68.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.7914	79.14%
P-glycoprotein inhibitior	-	0.4335	43.35%
P-glycoprotein substrate	-	0.6787	67.87%
CYP3A4 substrate	+	0.5892	58.92%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9131	91.31%
CYP3A4 inhibition	-	0.8992	89.92%
CYP2C9 inhibition	-	0.8088	80.88%
CYP2C19 inhibition	-	0.5464	54.64%
CYP2D6 inhibition	-	0.9500	95.00%
CYP1A2 inhibition	-	0.8456	84.56%
CYP2C8 inhibition	-	0.7544	75.44%
CYP inhibitory promiscuity	-	0.8070	80.70%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.7450	74.50%
Carcinogenicity (trinary)	Non-required	0.5493	54.93%
Eye corrosion	-	0.9392	93.92%
Eye irritation	-	0.8652	86.52%
Skin irritation	-	0.5902	59.02%
Skin corrosion	-	0.9697	96.97%
Ames mutagenesis	+	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3695	36.95%
Micronuclear	-	0.6200	62.00%
Hepatotoxicity	-	0.5125	51.25%
skin sensitisation	+	0.6630	66.30%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	-	0.6333	63.33%
Mitochondrial toxicity	-	0.8000	80.00%
Nephrotoxicity	+	0.5409	54.09%
Acute Oral Toxicity (c)	II	0.6907	69.07%
Estrogen receptor binding	+	0.5295	52.95%
Androgen receptor binding	+	0.7987	79.87%
Thyroid receptor binding	+	0.5418	54.18%
Glucocorticoid receptor binding	+	0.6231	62.31%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.5277	52.77%
Honey bee toxicity	+	0.9470	94.70%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.7300	73.00%
Fish aquatic toxicity	+	0.9910	99.10%

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	97.53%	96.09%
CHEMBL4040	P28482	MAP kinase ERK2	96.80%	83.82%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.39%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.02%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.39%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.34%	95.56%
CHEMBL340	P08684	Cytochrome P450 3A4	87.76%	91.19%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.67%	99.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.50%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.25%	95.89%
CHEMBL2996	Q05655	Protein kinase C delta	84.22%	97.79%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.69%	86.33%
CHEMBL2581	P07339	Cathepsin D	82.39%	98.95%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	81.51%	96.95%

Plants that contains it

• Tanacetum coccineum

Cross-Links

• PubChem: 5281547
• LOTUS: LTS0049251
• wikiData: Q27106172