Jasmolin II

Details

• Internal ID: fd7129b8-1f57-4eb0-bce6-0e3f83bf531a
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Fatty acid esters > Pyrethroids > Pyrethrins
• IUPAC Name: [(1S)-2-methyl-4-oxo-3-[(Z)-pent-2-enyl]cyclopent-2-en-1-yl] (1R,3R)-3-[(E)-3-methoxy-2-methyl-3-oxoprop-1-enyl]-2,2-dimethylcyclopropane-1-carboxylate
• SMILES (Canonical): CCC=CCC1=C(C(CC1=O)OC(=O)C2C(C2(C)C)C=C(C)C(=O)OC)C
• SMILES (Isomeric): CC/C=C\CC1=C([C@H](CC1=O)OC(=O)[C@@H]2[C@H](C2(C)C)/C=C(\C)/C(=O)OC)C
• InChI: InChI=1S/C22H30O5/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/h8-9,11,16,18-19H,7,10,12H2,1-6H3/b9-8-,13-11+/t16-,18+,19+/m1/s1
• InChI Key: WKNSDDMJXANVMK-XIGJTORUSA-N
• Popularity: 55 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₃₀O₅
• Molecular Weight: 374.50 g/mol
• Exact Mass: 374.20932405 g/mol
• Topological Polar Surface Area (TPSA): 69.70 Ų
• XlogP: 4.50
• Atomic LogP (AlogP): 3.94
• H-Bond Acceptor: 5
• H-Bond Donor: 0
• Rotatable Bonds: 7

Synonyms

• 1172-63-0
• A0S961SVRW
• (1S)-2-methyl-4-oxo-3-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-yl (1R,3R)-3-[(1E)-3-methoxy-2-methyl-3-oxoprop-1-en-1-yl]-2,2-dimethylcyclopropanecarboxylate
• [(1S)-2-methyl-4-oxo-3-[(Z)-pent-2-enyl]cyclopent-2-en-1-yl] (1R,3R)-3-[(E)-3-methoxy-2-methyl-3-oxoprop-1-enyl]-2,2-dimethylcyclopropane-1-carboxylate
• Jasmoline II
• Jasmolin II [BSI:ISO]
• UNII-A0S961SVRW
• Jasmoline II [ISO-French]
• JASMOLIN II [MI]
• JASMOLIN II [ISO]
• SCHEMBL116603
• DTXSID0042082
• CHEBI:39114
• LMPR0102060005
• (1R-(1alpha(S*(Z)),3beta(E)))-2-Methyl-4-oxo-3-(2-pentenyl)-2-cyclopenten-1-yl 3-(3-methoxy-2-methyl-3-oxo-1-propenyl)-2,2-dimethylcyclopropanecarboxylate
• J-003543
• Q24018184
• (1S)-2-METHYL-4-OXO-3-(2Z)-2-PENTENYL-2-CYCLOPENTEN-1-YL (1R,3R)-3-((1E)-3-METHOXY-2-METHYL-3-OXO-1-PROPENYL)-2,2-DIMETHYLCYCLOPROPANECARBOXYLATE
• (Z)-(S)-2-METHYL-4-OXO-3-(PENT-2-ENYL)CYCLOPENT-2-ENYL (E)-(1R,3R)-3-(2-METHOXYCARBONYLPROP-1-ENYL)-2,2-DIMETHYLCYCLOPROPANECARBOXYLATE
• [(1S)-2-methyl-4-oxo-3-[(Z)-pent-2-enyl]cyclopent-2-en-1-yl] (1R,3R)-3-[(E)-3-methoxy-2-methyl-3-oxo-prop-1-enyl]-2,2-dimethyl-cyclopropanecarboxylate
• Cyclopropanecarboxylic acid, 3-((1E)-3-methoxy-2-methyl-3-oxo-1-propenyl)-2,2-dimethyl-, (1S)-2-methyl-4-oxo-3-(2Z)-2-pentenyl-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-pentenyl)-2-cyclopenten-1-yl ester, (1R-(1alpha(S*(Z)),3beta(E)))-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9916	99.16%
Caco-2	+	0.6529	65.29%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7986	79.86%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8661	86.61%
OATP1B3 inhibitior	+	0.9490	94.90%
MATE1 inhibitior	-	0.6800	68.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.9356	93.56%
P-glycoprotein inhibitior	+	0.6632	66.32%
P-glycoprotein substrate	-	0.5785	57.85%
CYP3A4 substrate	+	0.6219	62.19%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9131	91.31%
CYP3A4 inhibition	-	0.8549	85.49%
CYP2C9 inhibition	-	0.8010	80.10%
CYP2C19 inhibition	-	0.6081	60.81%
CYP2D6 inhibition	-	0.9397	93.97%
CYP1A2 inhibition	-	0.8502	85.02%
CYP2C8 inhibition	-	0.6293	62.93%
CYP inhibitory promiscuity	-	0.8187	81.87%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.7248	72.48%
Carcinogenicity (trinary)	Non-required	0.6231	62.31%
Eye corrosion	-	0.9639	96.39%
Eye irritation	-	0.9208	92.08%
Skin irritation	-	0.7111	71.11%
Skin corrosion	-	0.9785	97.85%
Ames mutagenesis	+	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4430	44.30%
Micronuclear	-	0.6000	60.00%
Hepatotoxicity	+	0.5302	53.02%
skin sensitisation	-	0.5987	59.87%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	-	0.5778	57.78%
Mitochondrial toxicity	-	0.7125	71.25%
Nephrotoxicity	+	0.7146	71.46%
Acute Oral Toxicity (c)	II	0.6068	60.68%
Estrogen receptor binding	+	0.6762	67.62%
Androgen receptor binding	+	0.7047	70.47%
Thyroid receptor binding	+	0.5963	59.63%
Glucocorticoid receptor binding	+	0.7392	73.92%
Aromatase binding	-	0.5531	55.31%
PPAR gamma	-	0.5387	53.87%
Honey bee toxicity	+	0.8435	84.35%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.7600	76.00%
Fish aquatic toxicity	+	0.9899	98.99%

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	95.79%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.51%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.26%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.67%	91.11%
CHEMBL340	P08684	Cytochrome P450 3A4	90.14%	91.19%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.00%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.89%	95.56%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	84.47%	94.33%
CHEMBL2581	P07339	Cathepsin D	83.61%	98.95%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	81.02%	96.95%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.37%	91.07%

Plants that contains it

• Tanacetum coccineum

Cross-Links

• PubChem: 12304690
• LOTUS: LTS0217185
• wikiData: Q24018184