1.0 2010-04-08 22:04:29 UTC 2025-11-18 22:16:31 UTC FDB000234 Lambertianin C Lambertianin c 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. Lambertianin c is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Lambertianin c can be found in red raspberry, which makes lambertianin c a potential biomarker for the consumption of this food product. C123H80O78 2805.9045 2804.229343076 (1R,2S,19R,20S,22R)-36-[5-({[(1R,2S,19R,20S,22R)-36-[5-({[(1R,2S,19R,20S,22R)-7,8,9,12,13,14,28,29,30,33,34,35-dodecahydroxy-4,17,25,38-tetraoxo-3,18,21,24,39-pentaoxaheptacyclo[20.17.0.0²,¹⁹.0⁵,¹⁰.0¹¹,¹⁶.0²⁶,³¹.0³²,³⁷]nonatriaconta-5,7,9,11,13,15,26,28,30,32,34,36-dodecaen-20-yl]oxy}carbonyl)-2,3-dihydroxyphenoxy]-7,8,9,12,13,14,28,29,30,33,34,35-dodecahydroxy-4,17,25,38-tetraoxo-3,18,21,24,39-pentaoxaheptacyclo[20.17.0.0²,¹⁹.0⁵,¹⁰.0¹¹,¹⁶.0²⁶,³¹.0³²,³⁷]nonatriaconta-5,7,9,11,13,15,26,28,30,32,34,36-dodecaen-20-yl]oxy}carbonyl)-2,3-dihydroxyphenoxy]-7,8,9,12,13,14,28,29,30,33,34,35-dodecahydroxy-4,17,25,38-tetraoxo-3,18,21,24,39-pentaoxaheptacyclo[20.17.0.0²,¹⁹.0⁵,¹⁰.0¹¹,¹⁶.0²⁶,³¹.0³²,³⁷]nonatriaconta-5,7,9,11,13,15,26,28,30,32,34,36-dodecaen-20-yl 3,4,5-trihydroxybenzoate (1R,2S,19R,20S,22R)-36-[5-({[(1R,2S,19R,20S,22R)-36-[5-({[(1R,2S,19R,20S,22R)-7,8,9,12,13,14,28,29,30,33,34,35-dodecahydroxy-4,17,25,38-tetraoxo-3,18,21,24,39-pentaoxaheptacyclo[20.17.0.0²,¹⁹.0⁵,¹⁰.0¹¹,¹⁶.0²⁶,³¹.0³²,³⁷]nonatriaconta-5,7,9,11,13,15,26,28,30,32,34,36-dodecaen-20-yl]oxy}carbonyl)-2,3-dihydroxyphenoxy]-7,8,9,12,13,14,28,29,30,33,34,35-dodecahydroxy-4,17,25,38-tetraoxo-3,18,21,24,39-pentaoxaheptacyclo[20.17.0.0²,¹⁹.0⁵,¹⁰.0¹¹,¹⁶.0²⁶,³¹.0³²,³⁷]nonatriaconta-5,7,9,11,13,15,26,28,30,32,34,36-dodecaen-20-yl]oxy}carbonyl)-2,3-dihydroxyphenoxy]-7,8,9,12,13,14,28,29,30,33,34,35-dodecahydroxy-4,17,25,38-tetraoxo-3,18,21,24,39-pentaoxaheptacyclo[20.17.0.0²,¹⁹.0⁵,¹⁰.0¹¹,¹⁶.0²⁶,³¹.0³²,³⁷]nonatriaconta-5,7,9,11,13,15,26,28,30,32,34,36-dodecaen-20-yl 3,4,5-trihydroxybenzoate OC1=CC(=CC(O)=C1O)C(=O)O[C@@H]1O[C@@H]2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C(OC4=CC(=CC(O)=C4O)C(=O)O[C@@H]4O[C@@H]5COC(=O)C6=CC(O)=C(O)C(O)=C6C6=C(O)C(O)=C(O)C(OC7=CC(=CC(O)=C7O)C(=O)O[C@@H]7O[C@@H]8COC(=O)C9=CC(O)=C(O)C(O)=C9C9=C(O)C(O)=C(O)C=C9C(=O)O[C@H]8[C@@H]8OC(=O)C9=CC(O)=C(O)C(O)=C9C9=C(O)C(O)=C(O)C=C9C(=O)O[C@@H]78)=C6C(=O)O[C@H]5[C@@H]5OC(=O)C6=CC(O)=C(O)C(O)=C6C6=C(O)C(O)=C(O)C=C6C(=O)O[C@@H]45)=C3C(=O)O[C@H]2[C@@H]2OC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)O[C@@H]12 InChI=1S/C123H80O78/c124-33-1-20(2-34(125)66(33)138)106(167)199-121-104-101(194-114(175)28-12-42(133)72(144)82(154)55(28)58-31(117(178)197-104)15-45(136)75(147)85(58)157)96-50(188-121)18-183-110(171)24-8-38(129)77(149)87(159)60(24)62-64(119(180)191-96)98(93(165)91(163)89(62)161)186-48-6-22(4-36(127)68(48)140)108(169)201-123-105-102(195-115(176)29-13-43(134)73(145)83(155)56(29)59-32(118(179)198-105)16-46(137)76(148)86(59)158)97-51(189-123)19-184-111(172)25-9-39(130)78(150)88(160)61(25)63-65(120(181)192-97)99(94(166)92(164)90(63)162)185-47-5-21(3-35(126)67(47)139)107(168)200-122-103-100(193-113(174)27-11-41(132)71(143)81(153)54(27)57-30(116(177)196-103)14-44(135)74(146)84(57)156)95-49(187-122)17-182-109(170)23-7-37(128)69(141)79(151)52(23)53-26(112(173)190-95)10-40(131)70(142)80(53)152/h1-16,49-51,95-97,100-105,121-166H,17-19H2/t49-,50-,51-,95-,96-,97-,100+,101+,102+,103-,104-,105-,121+,122+,123+/m1/s1 KPIIQBZSYJKNLJ-PDZZWESLSA-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 tannins Organic compounds Phenylpropanoids and polyketides Tannins Hydrolyzable tannins Aromatic heteropolycyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Acetals Benzoyl derivatives Carboxylic acid esters Catechols Diarylethers Galloyl esters Hydrocarbon derivatives Lactones Monosaccharides Organic oxides Oxacyclic compounds Oxanes Phenol ethers Phenoxy compounds Polyols Pyrogallols and derivatives m-Hydroxybenzoic acid esters p-Hydroxybenzoic acid alkyl esters 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid Acetal Aromatic heteropolycyclic compound Benzenetriol Benzenoid Benzoate ester Benzoic acid or derivatives Benzoyl Carboxylic acid derivative Carboxylic acid ester Catechol Diaryl ether Dihydroxybenzoic acid Ether Gallic acid or derivatives Galloyl ester Hydrocarbon derivative Hydrolyzable tannin Lactone M-hydroxybenzoic acid ester Monocyclic benzene moiety Monosaccharide Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Oxane P-hydroxybenzoic acid alkyl ester P-hydroxybenzoic acid ester Phenol Phenol ether Phenoxy compound Polyol Pyrogallol derivative logp 4.42 ALOGPS logs -2.54 ALOGPS solubility 8.14e+00 g/l ALOGPS logp 10.28 ChemAxon pka_strongest_acidic 5.61 ChemAxon pka_strongest_basic -6.4 ChemAxon iupac (1R,2S,19R,20S,22R)-36-[5-({[(1R,2S,19R,20S,22R)-36-[5-({[(1R,2S,19R,20S,22R)-7,8,9,12,13,14,28,29,30,33,34,35-dodecahydroxy-4,17,25,38-tetraoxo-3,18,21,24,39-pentaoxaheptacyclo[20.17.0.0²,¹⁹.0⁵,¹⁰.0¹¹,¹⁶.0²⁶,³¹.0³²,³⁷]nonatriaconta-5,7,9,11,13,15,26,28,30,32,34,36-dodecaen-20-yl]oxy}carbonyl)-2,3-dihydroxyphenoxy]-7,8,9,12,13,14,28,29,30,33,34,35-dodecahydroxy-4,17,25,38-tetraoxo-3,18,21,24,39-pentaoxaheptacyclo[20.17.0.0²,¹⁹.0⁵,¹⁰.0¹¹,¹⁶.0²⁶,³¹.0³²,³⁷]nonatriaconta-5,7,9,11,13,15,26,28,30,32,34,36-dodecaen-20-yl]oxy}carbonyl)-2,3-dihydroxyphenoxy]-7,8,9,12,13,14,28,29,30,33,34,35-dodecahydroxy-4,17,25,38-tetraoxo-3,18,21,24,39-pentaoxaheptacyclo[20.17.0.0²,¹⁹.0⁵,¹⁰.0¹¹,¹⁶.0²⁶,³¹.0³²,³⁷]nonatriaconta-5,7,9,11,13,15,26,28,30,32,34,36-dodecaen-20-yl 3,4,5-trihydroxybenzoate ChemAxon average_mass 2805.9045 ChemAxon mono_mass 2804.229343076 ChemAxon smiles OC1=CC(=CC(O)=C1O)C(=O)O[C@@H]1O[C@@H]2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C(OC4=CC(=CC(O)=C4O)C(=O)O[C@@H]4O[C@@H]5COC(=O)C6=CC(O)=C(O)C(O)=C6C6=C(O)C(O)=C(O)C(OC7=CC(=CC(O)=C7O)C(=O)O[C@@H]7O[C@@H]8COC(=O)C9=CC(O)=C(O)C(O)=C9C9=C(O)C(O)=C(O)C=C9C(=O)O[C@H]8[C@@H]8OC(=O)C9=CC(O)=C(O)C(O)=C9C9=C(O)C(O)=C(O)C=C9C(=O)O[C@@H]78)=C6C(=O)O[C@H]5[C@@H]5OC(=O)C6=CC(O)=C(O)C(O)=C6C6=C(O)C(O)=C(O)C=C6C(=O)O[C@@H]45)=C3C(=O)O[C@H]2[C@@H]2OC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)O[C@@H]12 ChemAxon formula C123H80O78 ChemAxon inchi InChI=1S/C123H80O78/c124-33-1-20(2-34(125)66(33)138)106(167)199-121-104-101(194-114(175)28-12-42(133)72(144)82(154)55(28)58-31(117(178)197-104)15-45(136)75(147)85(58)157)96-50(188-121)18-183-110(171)24-8-38(129)77(149)87(159)60(24)62-64(119(180)191-96)98(93(165)91(163)89(62)161)186-48-6-22(4-36(127)68(48)140)108(169)201-123-105-102(195-115(176)29-13-43(134)73(145)83(155)56(29)59-32(118(179)198-105)16-46(137)76(148)86(59)158)97-51(189-123)19-184-111(172)25-9-39(130)78(150)88(160)61(25)63-65(120(181)192-97)99(94(166)92(164)90(63)162)185-47-5-21(3-35(126)67(47)139)107(168)200-122-103-100(193-113(174)27-11-41(132)71(143)81(153)54(27)57-30(116(177)196-103)14-44(135)74(146)84(57)156)95-49(187-122)17-182-109(170)23-7-37(128)69(141)79(151)52(23)53-26(112(173)190-95)10-40(131)70(142)80(53)152/h1-16,49-51,95-97,100-105,121-166H,17-19H2/t49-,50-,51-,95-,96-,97-,100+,101+,102+,103-,104-,105-,121+,122+,123+/m1/s1 ChemAxon inchikey KPIIQBZSYJKNLJ-PDZZWESLSA-N ChemAxon polar_surface_area 1310.54 ChemAxon refractivity 635.11 ChemAxon polarizability 252.7 ChemAxon rotatable_bond_count 13 ChemAxon acceptor_count 61 ChemAxon donor_count 43 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Andean blackberry Type 1 specific Rubus glaucus 520.0 520.0 520.0 mg/100 g Blackberry Type 1 specific Rubus 559.0 598.0 520.0 mg/100 g Red raspberry Type 1 specific Rubus idaeus 32247 35.6809 35.680899938 35.680899938 mg/100 g Tropical highland blackberry Type 1 specific Rubus adenotrichos 598.0 598.0 598.0 mg/100 g