1.02010-04-08 22:07:30 UTC2019-11-26 03:01:34 UTCFDB007228Rugosin ARugosin a is a member of the class of compounds known as hydrolyzable tannins. Hydrolyzable tannins are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit. Rugosin a is slightly soluble (in water) and a weakly acidic compound (based on its pKa). Rugosin a can be found in cloves, which makes rugosin a a potential biomarker for the consumption of this food product.C48H34O311106.7651106.108404373,4,5-trihydroxy-2-{[3,4,5,22,23-pentahydroxy-8,18-dioxo-11,12,13-tris(3,4,5-trihydroxybenzoyloxy)-9,14,17-trioxatetracyclo[17.4.0.0²,⁷.0¹⁰,¹⁵]tricosa-1(19),2(7),3,5,20,22-hexaen-21-yl]oxy}benzoic acid3,4,5-trihydroxy-2-{[3,4,5,22,23-pentahydroxy-8,18-dioxo-11,12,13-tris(3,4,5-trihydroxybenzoyloxy)-9,14,17-trioxatetracyclo[17.4.0.0²,⁷.0¹⁰,¹⁵]tricosa-1(19),2(7),3,5,20,22-hexaen-21-yl]oxy}benzoic acidOC(=O)C1=C(OC2=CC3=C(C(O)=C2O)C2=C(C=C(O)C(O)=C2O)C(=O)OC2C(COC3=O)OC(OC(=O)C3=CC(O)=C(O)C(O)=C3)C(OC(=O)C3=CC(O)=C(O)C(O)=C3)C2OC(=O)C2=CC(O)=C(O)C(O)=C2)C(O)=C(O)C(O)=C1InChI=1S/C48H34O31/c49-17-1-11(2-18(50)29(17)57)43(68)77-40-39-26(75-48(79-45(70)13-5-21(53)31(59)22(54)6-13)41(40)78-44(69)12-3-19(51)30(58)20(52)4-12)10-73-46(71)15-9-25(74-38-16(42(66)67)8-24(56)33(61)37(38)65)34(62)36(64)28(15)27-14(47(72)76-39)7-23(55)32(60)35(27)63/h1-9,26,39-41,48-65H,10H2,(H,66,67)OMQLRKHSGHBOQC-UHFFFAOYSA-N belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit.Hydrolyzable tanninsOrganic compoundsPhenylpropanoids and polyketidesTanninsHydrolyzable tanninsAromatic heteropolycyclic compounds1-hydroxy-2-unsubstituted benzenoids1-hydroxy-4-unsubstituted benzenoidsAcetalsBenzoic acidsBenzoyl derivativesCarboxylic acid estersCarboxylic acidsDiarylethersGallic acidsGalloyl estersHexacarboxylic acids and derivativesHydrocarbon derivativesLactonesMonosaccharidesOrganic oxidesOxacyclic compoundsOxanesPhenol ethersPhenoxy compoundsPolyolsPyrogallols and derivativesm-Hydroxybenzoic acid estersp-Hydroxybenzoic acid alkyl esters1-hydroxy-2-unsubstituted benzenoid1-hydroxy-4-unsubstituted benzenoidAcetalAromatic heteropolycyclic compoundBenzenetriolBenzenoidBenzoate esterBenzoic acidBenzoic acid or derivativesBenzoylCarboxylic acidCarboxylic acid derivativeCarboxylic acid esterDiaryl etherDihydroxybenzoic acidEtherGallic acidGallic acid or derivativesGalloyl esterHexacarboxylic acid or derivativesHydrocarbon derivativeHydrolyzable tanninHydroxybenzoic acidLactoneM-hydroxybenzoic acid esterMonocyclic benzene moietyMonosaccharideOrganic oxideOrganic oxygen compoundOrganoheterocyclic compoundOrganooxygen compoundOxacycleOxaneP-hydroxybenzoic acid alkyl esterP-hydroxybenzoic acid esterPhenolPhenol etherPhenoxy compoundPolyolPyrogallol derivativelogp3.76logs-2.96solubility1.21e+00 g/llogp4.82pka_strongest_acidic3.45pka_strongest_basic-6.2iupac3,4,5-trihydroxy-2-{[3,4,5,22,23-pentahydroxy-8,18-dioxo-11,12,13-tris(3,4,5-trihydroxybenzoyloxy)-9,14,17-trioxatetracyclo[17.4.0.0²,⁷.0¹⁰,¹⁵]tricosa-1(19),2(7),3,5,20,22-hexaen-21-yl]oxy}benzoic acidaverage_mass1106.765mono_mass1106.10840437smilesOC(=O)C1=C(OC2=CC3=C(C(O)=C2O)C2=C(C=C(O)C(O)=C2O)C(=O)OC2C(COC3=O)OC(OC(=O)C3=CC(O)=C(O)C(O)=C3)C(OC(=O)C3=CC(O)=C(O)C(O)=C3)C2OC(=O)C2=CC(O)=C(O)C(O)=C2)C(O)=C(O)C(O)=C1formulaC48H34O31inchiInChI=1S/C48H34O31/c49-17-1-11(2-18(50)29(17)57)43(68)77-40-39-26(75-48(79-45(70)13-5-21(53)31(59)22(54)6-13)41(40)78-44(69)12-3-19(51)30(58)20(52)4-12)10-73-46(71)15-9-25(74-38-16(42(66)67)8-24(56)33(61)37(38)65)34(62)36(64)28(15)27-14(47(72)76-39)7-23(55)32(60)35(27)63/h1-9,26,39-41,48-65H,10H2,(H,66,67)inchikeyOMQLRKHSGHBOQC-UHFFFAOYSA-Npolar_surface_area531.17refractivity251.28polarizability96.88rotatable_bond_count12acceptor_count25donor_count18physiological_charge-2formal_charge0Specdb::MsMs106176Specdb::MsMs106177Specdb::MsMs106178Specdb::MsMs172845Specdb::MsMs172846Specdb::MsMs172847Specdb::MsMs3603812Specdb::MsMs3603813Specdb::MsMs3603814Specdb::MsMs3603815Specdb::MsMs3603816Specdb::MsMs3603817ClovesType 1specificSyzygium aromaticum2198681.621.621.62mg/100 gxanthine oxidase inhibitor1431An EC 1.17.3.* (oxidoreductase acting on CH or CH2 with oxygen as acceptor) inhibitor that interferes with the action of xanthine oxidase (EC 1.17.3.2).