1.0 2010-04-08 22:05:00 UTC 2020-02-24 19:10:23 UTC FDB001514 1,5-Dicaffeoylquinic acid Cynarine is a hydroxycinnamic acid and a biologically active chemical constituent of artichoke. Chemically, it is an ester formed from quinic acid and two units of caffeic acid. 1,5-Dicaffeoylquinic acid is found in cardoon, globe artichoke, and fennel. 1,5-Di-O-caffeoylquinic acid Cinarine Cynarin Cynarine C25H24O12 516.4509 516.126776232 (1R,3R,4S,5R)-1,3-bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-4,5-dihydroxycyclohexane-1-carboxylic acid cynarine 30964-13-7 O[C@@H]1C[C@](C[C@@H](OC(=O)\C=C\C2=CC=C(O)C(O)=C2)[C@H]1O)(OC(=O)\C=C\C1=CC=C(O)C(O)=C1)C(O)=O InChI=1S/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(31)36-20-12-25(24(34)35,11-19(30)23(20)33)37-22(32)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-30,33H,11-12H2,(H,34,35)/b7-3+,8-4+/t19-,20-,23+,25-/m1/s1 YDDUMTOHNYZQPO-RVXRWRFUSA-N belongs to the class of organic compounds known as quinic acids and derivatives. Quinic acids and derivatives are compounds containing a quinic acid moiety (or a derivative thereof), which is a cyclitol made up of a cyclohexane ring that bears four hydroxyl groups at positions 1,3.4, and 5, as well as a carboxylic acid at position 1. Quinic acids and derivatives Organic compounds Organic oxygen compounds Organooxygen compounds Alcohols and polyols Aromatic homomonocyclic compounds 1,2-diols 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Carbonyl compounds Carboxylic acids Catechols Cinnamic acid esters Coumaric acids and derivatives Cyclohexanols Enoate esters Fatty acid esters Hydrocarbon derivatives Organic oxides Styrenes Tricarboxylic acids and derivatives 1,2-diol 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid Alpha,beta-unsaturated carboxylic ester Aromatic homomonocyclic compound Benzenoid Carbonyl group Carboxylic acid Carboxylic acid derivative Carboxylic acid ester Catechol Cinnamic acid ester Cinnamic acid or derivatives Coumaric acid or derivatives Cyclohexanol Enoate ester Fatty acid ester Fatty acyl Hydrocarbon derivative Hydroxycinnamic acid or derivatives Monocyclic benzene moiety Organic oxide Phenol Quinic acid Secondary alcohol Styrene Tricarboxylic acid or derivatives alkyl caffeate ester quinic acid logp 2.07 ALOGPS logs -3.58 ALOGPS solubility 1.37e-01 g/l ALOGPS logp 2.16 ChemAxon pka_strongest_acidic 3.18 ChemAxon pka_strongest_basic -3.2 ChemAxon iupac (1R,3R,4S,5R)-1,3-bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-4,5-dihydroxycyclohexane-1-carboxylic acid ChemAxon average_mass 516.4509 ChemAxon mono_mass 516.126776232 ChemAxon smiles O[C@@H]1C[C@](C[C@@H](OC(=O)\C=C\C2=CC=C(O)C(O)=C2)[C@H]1O)(OC(=O)\C=C\C1=CC=C(O)C(O)=C1)C(O)=O ChemAxon formula C25H24O12 ChemAxon inchi InChI=1S/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(31)36-20-12-25(24(34)35,11-19(30)23(20)33)37-22(32)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-30,33H,11-12H2,(H,34,35)/b7-3+,8-4+/t19-,20-,23+,25-/m1/s1 ChemAxon inchikey YDDUMTOHNYZQPO-RVXRWRFUSA-N ChemAxon polar_surface_area 211.28 ChemAxon refractivity 126.76 ChemAxon polarizability 50.19 ChemAxon rotatable_bond_count 9 ChemAxon acceptor_count 10 ChemAxon donor_count 7 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 15910 Specdb::CMs 41742 Specdb::MsMs 301228 Specdb::MsMs 301229 Specdb::MsMs 301230 Specdb::MsMs 343705 Specdb::MsMs 343706 Specdb::MsMs 343707 Specdb::MsMs 2236504 Specdb::MsMs 2236857 Specdb::MsMs 2238672 Specdb::MsMs 2238918 Specdb::MsMs 2240640 Specdb::MsMs 2241041 Specdb::MsMs 2242704 Specdb::MsMs 2243148 Specdb::MsMs 2244851 Specdb::MsMs 2245277 Specdb::MsMs 2308641 Specdb::MsMs 2308642 Specdb::MsMs 2308643 Specdb::MsMs 2653937 Specdb::MsMs 2653938 Specdb::MsMs 2653939 HMDB30093 #<Reference:0x000055ce32103e38> Cardoon Type 1 specific Cynara cardunculus 4265 Fennel Type 1 specific Foeniculum vulgare 48038 Globe artichoke Type 1 specific Cynara scolymus 59895 Anti bacterial 145 A substance that kills or slows the growth of bacteria. Anti dyspeptic 242 Any substance introduced into a living organism with therapeutic or diagnostic purpose. Anti lipolytic 406 Anti sunburn 635 Any substance introduced into a living organism with therapeutic or diagnostic purpose. Anti-staphylococcic 627 A substance that kills or slows the growth of bacteria. Anti-streptococcic 631 A substance that kills or slows the growth of bacteria. Central nervous system active 811 A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system. Cholagogue 800 Choleretic 801 Cholesterolytic 802 Collagen-sparing 822 Cytoprotective 857 Diuretic 883 An agent that promotes the excretion of urine through its effects on kidney function. Hepatoprotective 981 Any compound that is able to prevent damage to the liver. Hepatoregenerative 982 Any compound that is able to prevent damage to the liver. Hepatotonic 983 Hyperemic 1004 Hypocholesterolemic 1016 Hypolipidemic 1020 Hypotriglyceridemic 1024 Lipolytic 1074 Pesticide 1210 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests. Sweetener 1341 Substance that sweeten food, beverages, medications, etc.