1.0 2010-04-08 22:11:46 UTC 2019-11-26 03:11:25 UTC FDB015308 Cynaropicrin Constituent of Cynara scolymus (artichoke). Cynaropicrin is found in cardoon, globe artichoke, and root vegetables. Cynaropicrin C19H22O6 346.3744 346.141638436 8-hydroxy-3,6,9-trimethylidene-2-oxo-dodecahydroazuleno[4,5-b]furan-4-yl 2-(hydroxymethyl)prop-2-enoate saupirin 35730-78-0 OCC(=C)C(=O)OC1CC(=C)C2CC(O)C(=C)C2C2OC(=O)C(=C)C12 InChI=1S/C19H22O6/c1-8-5-14(24-18(22)9(2)7-20)16-11(4)19(23)25-17(16)15-10(3)13(21)6-12(8)15/h12-17,20-21H,1-7H2 KHSCYOFDKADJDJ-UHFFFAOYSA-N belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative. Guaianolides and derivatives Organic compounds Lipids and lipid-like molecules Prenol lipids Terpene lactones Aliphatic heteropolycyclic compounds Beta hydroxy acids and derivatives Carbonyl compounds Cyclic alcohols and derivatives Dicarboxylic acids and derivatives Enoate esters Gamma butyrolactones Guaianes Hydrocarbon derivatives Organic oxides Oxacyclic compounds Primary alcohols Secondary alcohols Tetrahydrofurans Alcohol Aliphatic heteropolycyclic compound Alpha,beta-unsaturated carboxylic ester Beta-hydroxy acid Carbonyl group Carboxylic acid derivative Carboxylic acid ester Cyclic alcohol Dicarboxylic acid or derivatives Enoate ester Gamma butyrolactone Guaiane sesquiterpenoid Guaianolide-skeleton Hydrocarbon derivative Hydroxy acid Lactone Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Primary alcohol Secondary alcohol Sesquiterpenoid Tetrahydrofuran Guaianolide sesquiterpene lactone logp 0.54 ALOGPS logs -2.34 ALOGPS solubility 1.60e+00 g/l ALOGPS logp 1.04 ChemAxon pka_strongest_acidic 6.63 ChemAxon pka_strongest_basic -2.8 ChemAxon iupac 8-hydroxy-3,6,9-trimethylidene-2-oxo-dodecahydroazuleno[4,5-b]furan-4-yl 2-(hydroxymethyl)prop-2-enoate ChemAxon average_mass 346.3744 ChemAxon mono_mass 346.141638436 ChemAxon smiles OCC(=C)C(=O)OC1CC(=C)C2CC(O)C(=C)C2C2OC(=O)C(=C)C12 ChemAxon formula C19H22O6 ChemAxon inchi InChI=1S/C19H22O6/c1-8-5-14(24-18(22)9(2)7-20)16-11(4)19(23)25-17(16)15-10(3)13(21)6-12(8)15/h12-17,20-21H,1-7H2 ChemAxon inchikey KHSCYOFDKADJDJ-UHFFFAOYSA-N ChemAxon polar_surface_area 93.06 ChemAxon refractivity 88.99 ChemAxon polarizability 35.06 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 14666 Specdb::CMs 44864 Specdb::CMs 163901 Specdb::MsMs 86136 Specdb::MsMs 86137 Specdb::MsMs 86138 Specdb::MsMs 148389 Specdb::MsMs 148390 Specdb::MsMs 148391 Specdb::MsMs 2821862 Specdb::MsMs 2821863 Specdb::MsMs 2821864 Specdb::MsMs 2857776 Specdb::MsMs 2857777 Specdb::MsMs 2857778 HMDB36423 #<Reference:0x000055ce3008e540> Cardoon Type 1 specific Cynara cardunculus 4265 Globe artichoke Type 1 specific Cynara scolymus 59895 Root vegetables Unknown generic bitter