Compound: Cynaropicrin
SMILES: O=C1O[C@@H]2[C@H]3C(=C)[C@@H](O)C[C@H]3C(=C)C[C@@H]([C@H]2C1=C)OC(=O)C(=C)CO
InChIKey: KHSCYOFDKADJDJ-NQLMQOPMSA-N
Synonyms: Cynaropicrin, 35730-78-0, 2-Propenoic acid, 2-(hydroxymethyl)-, (3aR,4S,6aR,8S,9aR,9bR)-dodecahydro-8-hydroxy-3,6,9-tris(methylene)-2-oxoazuleno(4,5-b)furan-4-yl ester, M9233789I9, [(3aR,4S,6aR,8S,9aR,9bR)-8-hydroxy-3,6,9-trimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-4-yl] 2-(hydroxymethyl)prop-2-enoate, 2-Propenoic acid, 2-(hydroxymethyl)-, dodecahydro-8-hydroxy-3,6,9-tris(methylene)-2-oxoazuleno(4,5-b)furan-4-yl ester, (3aR-(3aalpha,4alpha,6aalpha,8beta,9aalpha,9bbeta))-, ((3aR,4S,6aR,8S,9aR,9bR)-8-hydroxy-3,6,9-trimethylene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydroazuleno(4,5-b)furan-4-yl) 2-(hydroxymethyl)prop-2-enoate, ((3aR,4S,6aR,8S,9aR,9bR)-8-hydroxy-3,6,9-trimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydroazuleno(4,5-b)furan-4-yl) 2-(hydroxymethyl)prop-2-enoate, [(3aR,4S,6aR,8S,9aR,9bR)-8-hydroxy-3,6,9-trimethylene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-4-yl] 2-(hydroxymethyl)prop-2-enoate, RefChem:34088, 689-765-5, Cynaropikrin, CHEMBL374146, Cynaropicrin (Standard), CHEBI:4038, MEGxp0_001095, orb1684669, orb3139522, SCHEMBL1711811, ACon1_000045, HY-N2350R, DTXSID20957143, UNII-M9233789I9, HY-N2350, BDBM50194430, AKOS032971358, CS-8041, EBC-513120, FS-8077, NCGC00168845-01, NCGC00168845-02, (3AR,4S,6AR,8S,9AR,9BR)-8-HYDROXY-3,6,9-TRIMETHYLIDENE-2-OXO-DODECAHYDROAZULENO[4,5-B]FURAN-4-YL 2-(HYDROXYMETHYL)PROP-2-ENOATE, DA-52252, XC160151, NS00094008, Cynaropicrin - Cynara cardunculus (artichoke), C09385, G16186, BRD-K51428447-001-01-5, Q15410905, (3aR,4S,6aR,8S,9aR,9bR)-8-hydroxy-3,6,9-trimethylidene-2-oxododecahydroazuleno[4,5-b]furan-4-yl 2-(hydroxymethyl)prop-2-enoate, 2-PROPENOIC ACID, 2-(HYDROXYMETHYL)-, DODECAHYDRO-8-HYDROXY-3,6,9-TRIS(METHYLENE)-2-OXOAZULENO(4,5-B)FURAN-4-YL ESTER, (3AR-(3A.ALPHA.,4.ALPHA.,6A.ALPHA.,8.BETA.,9A.ALPHA.,9B.BETA.))-, 8-Hydroxy-3,6,9-trimethylidene-2-oxododecahydroazuleno[4,5-b]furan-4-yl 2-(hydroxymethyl)prop-2-enoate
Theoretical properties:
molecular_formula: C19H22O6
molecular_weight: 346.4 g/mol
exact_mass: 346.14163842 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 6
rotatable_bond_count: 4
heavy_atom_count: 25
topological_polar_surface_area: 93.1 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Cynaropicrin is a sesquiterpene lactone.
chembl: CYNAROPICRIN is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: Cynaropicrin is a sesquiterpene lactone of the guaianolide type found mainly in leaves of artichoke plants. It is one of the compounds that gives the artichoke its characteristic bitterness. It is found in artichoke leaves with an abundance of approximately 87 g/kg, but can hardly be found in other parts of the plant. Cynaropicrin makes up about 0.7% of leaf extracts of the artichoke. It exhibits a large diversity of bioactivities and shows properties such as anti-inflammatory, antifeedant and activation of bitter sensory receptors, but has not yet been used in medicine. Despite its pharmacologically beneficial properties, it can be toxic in higher doses. The compound has attracted attention in recent years as a potential anticancer drug.