Jasmolin I

Details

• Internal ID: 4f86598c-fb4e-4fb7-9219-d57d05a7f142
• 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)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate
• SMILES (Canonical): CCC=CCC1=C(C(CC1=O)OC(=O)C2C(C2(C)C)C=C(C)C)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)C
• InChI: InChI=1S/C21H30O3/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/h8-9,11,16,18-19H,7,10,12H2,1-6H3/b9-8-/t16-,18+,19+/m1/s1
• InChI Key: NZKIRHFOLVYKFT-VUMXUWRFSA-N
• Popularity: 76 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₃₀O₃
• Molecular Weight: 330.50 g/mol
• Exact Mass: 330.21949481 g/mol
• Topological Polar Surface Area (TPSA): 43.40 Ų
• XlogP: 5.40

Synonyms

• 4466-14-2
• Jasmoline I
• JASMOLIN 1
• UNII-E11IV49HVI
• Jasmoline I [ISO-French]
• E11IV49HVI
• JASMOLIN I [MI]
• DTXSID5042081
• CHEBI:39113
• (1S)-2-methyl-4-oxo-3-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-yl (1R,3R)-2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropanecarboxylate
• [(1S)-2-methyl-4-oxo-3-[(Z)-pent-2-enyl]cyclopent-2-en-1-yl] (1R,3R)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate
• Jasmoline I (ISO-French)
• (1R-(1alpha(S*(Z)),3beta))-2-Methyl-4-oxo-3-(2-pentenyl)-2-cyclopenten-1-yl 2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate
• Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-, (1S)-2-methyl-4-oxo-3-(2Z)-2-pentenyl-2-cyclopenten-1-yl ester, (1R,3R)-
• (1S)-2-METHYL-4-OXO-3-(2Z)-2-PENTENYL-2-CYCLOPENTEN-1-YL (1R,3R)-2,2-DIMETHYL-3-(2-METHYL-1-PROPENYL)CYCLOPROPANECARBOXYLATE
• (Z)-(S)-2-METHYL-4-OXO-3-(PENT-2-ENYL)CYCLOPENT-2-ENYL (1R,3R)-2,2-DIMETHYL-3-(2-METHYLPROP-1-ENYL)CYCLOPROPANECARBOXYLATE
• Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-, 2-methyl-4-oxo-3-(2-pentenyl)-2-cyclopenten-1-yl ester, (1R-(1alpha(S*(Z)),3beta))-
• ((1S)-2-methyl-4-oxo-3-((Z)-pent-2-enyl)cyclopent-2-en-1-yl) (1R,3R)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate
• (1S)-2-methyl-4-oxo-3-((2Z)-pent-2-en-1-yl)cyclopent-2-en-1-yl (1R,3R)-2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropanecarboxylate
• 2-Methyl-4-oxo-3-((2E)-pent-2-en-1-yl)cyclopent-2-en-1-yl 2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropane-1-carboxylic acid
• 2-Methyl-4-oxo-3-[(2E)-pent-2-en-1-yl]cyclopent-2-en-1-yl 2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropane-1-carboxylic acid
• Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-, 2-methyl-4-oxo-3-(2-pentenyl)-2-cyclopenten-1-yl ester, [1R-[1.alpha.[S*(Z)],3.beta.]]-
• Pyrethrin (jasmolin I)
• RefChem:150363
• DTXCID3022081
• 2-methyl-4-oxo-3-(pent-2-en-1-yl)cyclopent-2-en-1-yl 2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropane-1-carboxylate
• Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-, 2-methyl-4-oxo-3-(2-pentenyl)-2-cyclopenten-1-yl ester
• Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methylpropenyl)-, ester with 4-hydroxy-3-methyl-2-(2-pentenyl)-2-cyclopenten-1-one
• NZKIRHFOLVYKFT-CMDGGOBGSA-N
• Jasmolin I + Cinerin I (Mixture)
• (S)-2-Methyl-4-oxo-3-((Z)-pent-2-en-1-yl)cyclopent-2-en-1-yl (1R,3R)-2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropane-1-carboxylate
• SCHEMBL14208324
• NZKIRHFOLVYKFT-VUMXUWRFSA-N
• C12H30O3
• LMPR0102060004
• (1S)-2-methyl-4-oxo-3-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-yl (1R,3R)-2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropane-1-carboxylate
• FJ158204
• Q24018089
• [(1S)-2-methyl-4-oxo-3-[(Z)-pent-2-enyl]cyclopent-2-en-1-yl] (1R,3R)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
No predicted properties yet!

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	96.48%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.75%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.90%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.45%	91.11%
CHEMBL340	P08684	Cytochrome P450 3A4	87.77%	91.19%
CHEMBL2581	P07339	Cathepsin D	86.91%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.56%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.32%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.98%	86.33%
CHEMBL253	P34972	Cannabinoid CB2 receptor	83.21%	97.25%
CHEMBL2996	Q05655	Protein kinase C delta	82.86%	97.79%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	82.22%	96.95%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	81.60%	91.71%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.16%	97.09%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.08%	94.33%

Plants that contains it

• Tanacetum coccineum

Cross-Links

• PubChem: 12304687
• LOTUS: LTS0127753
• wikiData: Q24018089