1.0 2010-04-08 22:10:03 UTC 2019-11-26 03:06:23 UTC FDB012205 Procyanidin B3 Present in red wine. Occurs in Fragaria subspecies Procyanidin B3 is found in many foods, some of which are quince, strawberry, bilberry, and japanese persimmon. 2,3-trans-proanthocyanidin Afzelechin-(4alpha->8)-afzelechin C-(4a,8)-C Catechin-(4a->8)-catechin Catechin-(4alpha->8)-catechin Catechin-(4α->8)-catechin Catechin(4a->8)catechin Proanthocyanidin B3 Procyanidin B3 C30H26O12 578.526 578.142426277 (2R,3S)-2-(3,4-dihydroxyphenyl)-8-[(2R,3S,4S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]-3,4-dihydro-2H-1-benzopyran-3,5,7-triol procyanidin B3 23567-23-9 [H][C@@]1([C@H](O)[C@H](OC2=CC(O)=CC(O)=C12)C1=CC(O)=C(O)C=C1)C1=C(O)C=C(O)C2=C1O[C@@H]([C@@H](O)C2)C1=CC(O)=C(O)C=C1 InChI=1S/C30H26O12/c31-13-7-20(37)24-23(8-13)41-29(12-2-4-16(33)19(36)6-12)27(40)26(24)25-21(38)10-17(34)14-9-22(39)28(42-30(14)25)11-1-3-15(32)18(35)5-11/h1-8,10,22,26-29,31-40H,9H2/t22-,26-,27-,28+,29+/m0/s1 XFZJEEAOWLFHDH-AVFWISQGSA-N belongs to the class of organic compounds known as biflavonoids and polyflavonoids. These are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''. Biflavonoids and polyflavonoids Organic compounds Phenylpropanoids and polyketides Flavonoids Biflavonoids and polyflavonoids Aromatic heteropolycyclic compounds 1-benzopyrans 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids 3'-hydroxyflavonoids 3-hydroxyflavonoids 4'-hydroxyflavonoids 5-hydroxyflavonoids 7-hydroxyflavonoids Alkyl aryl ethers B-type proanthocyanidins Benzene and substituted derivatives Catechins Catechols Hydrocarbon derivatives Oxacyclic compounds Polyols Secondary alcohols 1-benzopyran 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid 3'-hydroxyflavonoid 3-hydroxyflavonoid 4'-hydroxyflavonoid 5-hydroxyflavonoid 7-hydroxyflavonoid Alcohol Alkyl aryl ether Aromatic heteropolycyclic compound B-type proanthocyanidin Benzenoid Benzopyran Bi- and polyflavonoid skeleton Catechin Catechol Chromane Ether Flavan Flavan-3-ol Hydrocarbon derivative Hydroxyflavonoid Monocyclic benzene moiety Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Phenol Polyol Proanthocyanidin Secondary alcohol Proanthocyanidins biflavonoid hydroxyflavan polyphenol proanthocyanidin logp 2.29 ALOGPS logs -3.62 ALOGPS solubility 1.38e-01 g/l ALOGPS logp 3.12 ChemAxon pka_strongest_acidic 8.69 ChemAxon pka_strongest_basic -5.2 ChemAxon iupac (2R,3S)-2-(3,4-dihydroxyphenyl)-8-[(2R,3S,4S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]-3,4-dihydro-2H-1-benzopyran-3,5,7-triol ChemAxon average_mass 578.526 ChemAxon mono_mass 578.142426277 ChemAxon smiles [H][C@@]1([C@H](O)[C@H](OC2=CC(O)=CC(O)=C12)C1=CC(O)=C(O)C=C1)C1=C(O)C=C(O)C2=C1O[C@@H]([C@@H](O)C2)C1=CC(O)=C(O)C=C1 ChemAxon formula C30H26O12 ChemAxon inchi InChI=1S/C30H26O12/c31-13-7-20(37)24-23(8-13)41-29(12-2-4-16(33)19(36)6-12)27(40)26(24)25-21(38)10-17(34)14-9-22(39)28(42-30(14)25)11-1-3-15(32)18(35)5-11/h1-8,10,22,26-29,31-40H,9H2/t22-,26-,27-,28+,29+/m0/s1 ChemAxon inchikey XFZJEEAOWLFHDH-AVFWISQGSA-N ChemAxon polar_surface_area 220.76 ChemAxon refractivity 146.51 ChemAxon polarizability 57.27 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 12 ChemAxon donor_count 10 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 44784 Specdb::MsMs 44785 Specdb::MsMs 44786 Specdb::MsMs 136902 Specdb::MsMs 136903 Specdb::MsMs 136904 Specdb::MsMs 2332619 Specdb::MsMs 2332620 Specdb::MsMs 2332621 Specdb::MsMs 2633000 Specdb::MsMs 2633001 Specdb::MsMs 2633002 Specdb::CMs 43616 Specdb::CMs 68643 Specdb::CMs 282504 Specdb::CMs 388798 Specdb::CMs 388799 Specdb::CMs 388800 Specdb::CMs 388801 Specdb::CMs 388802 Specdb::CMs 388803 Specdb::CMs 388804 Specdb::CMs 388805 Specdb::CMs 388806 Specdb::CMs 388807 Specdb::CMs 388808 Specdb::CMs 388809 Specdb::CMs 388810 Specdb::CMs 388811 Specdb::CMs 388812 Specdb::CMs 388813 Specdb::CMs 388814 Specdb::CMs 388815 Specdb::CMs 388816 Specdb::CMs 388817 Specdb::CMs 388818 Specdb::CMs 388819 HMDB33974 #<Reference:0x000055ce30671ea8> Alcoholic beverages Unknown generic Amaranth Type 1 specific Amaranthus 3564 Annual wild rice Type 1 specific Zizania aquatica 75727 Apple Type 1 specific Malus pumila 283210 0.038333 0.229999997 0.0 mg/100 g Apple cider Type 2 specific 0.0 0.0 0.0 mg/100 g Apricot Type 1 specific Prunus armeniaca 36596 0.05 0.050000002 0.050000002 mg/100 g Avocado Type 1 specific Persea americana 3435 0.0 0.0 0.0 mg/100 g Banana Type 1 specific Musa acuminata 4641 0.0 0.0 0.0 mg/100 g Barley Type 1 specific Hordeum vulgare 4513 10.9 10.899999936 10.899999936 mg/100 g Beer Type 2 specific 0.155 0.154999998 0.154999998 mg/100 g Bilberry Type 1 specific Vaccinium myrtillus 180763 Black tea Type 1 0.43 0.49000001 0.370000005 mg/100 g Breakfast cereal Type 2 specific Broad bean Type 1 specific Vicia faba 3906 8.17 8.170000076 8.170000076 mg/100 g Bulgur Type 2 specific Carrot Type 1 specific Daucus carota ssp. sativus 79200 0.0 0.0 0.0 mg/100 g Cereals and cereal products Unknown generic Chestnut Type 1 specific Castanea 21019 0.01 0.01 0.01 mg/100 g Chickpea Type 1 specific Cicer arietinum 3827 0.0 0.0 0.0 mg/100 g Common bean Type 1 specific Phaseolus vulgaris 3885 0.446667 0.820000013 0.029999999 mg/100 g Common buckwheat Type 1 specific Fagopyrum esculentum 3617 Common grape Type 1 specific Vitis vinifera 29760 0.31503 0.936162175 0.0 mg/100 g Common hazelnut Type 1 specific Corylus avellana 13451 Common pea Type 1 specific Pisum sativum 3888 0.0 0.0 0.0 mg/100 g Common wheat Type 1 specific Triticum aestivum 4565 0.0 0.0 0.0 mg/100 g Corn Type 1 specific Zea mays 4577 Cucurbita Type 1 specific Cucurbita 3660 0.0 0.0 0.0 mg/100 g Custard apple Type 1 specific Annona reticulata 301862 0.31 0.310000002 0.310000002 mg/100 g Eggplant Type 1 specific Solanum melongena 4111 0.0 0.0 0.0 mg/100 g European plum Type 1 specific Prunus domestica 3758 1.0 1.0 1.0 mg/100 g Fig Type 1 specific Ficus carica 3494 0.03 0.029999999 0.029999999 mg/100 g Flour Type 2 specific Fox grape Type 1 specific Vitis labrusca 103355 3.13 5.259999752 1.00000003 mg/100 g Fruits Unknown generic Garden tomato (var.) Type 1 specific Solanum lycopersicum var. lycopersicum 397755 0.0 0.0 0.0 mg/100 g Grape wine Type 2 specific 3.156808 9.467567238 0.0 mg/100 g Green bean Type 1 specific Phaseolus vulgaris 3885 0.655 0.820000013 0.49000001 mg/100 g Green bell pepper Type 1 specific Capsicum annuum 4072 0.0 0.0 0.0 mg/100 g Green tea Type 1 0.43 0.49000001 0.370000005 mg/100 g Green zucchini Type 1 specific Cucurbita pepo var. cylindrica 0.0 0.0 0.0 mg/100 g Guava Type 1 specific Psidium guajava 120290 Hard wheat Type 1 specific Triticum durum 4567 Herbal tea Type 1 Italian sweet red pepper Type 1 specific Capsicum annuum 4072 0.0 0.0 0.0 mg/100 g Japanese persimmon Type 1 specific Diospyros kaki 35925 0.01 0.01 0.01 mg/100 g Kiwi Type 1 specific Actinidia chinensis 3625 0.0 0.0 0.0 mg/100 g Lentils Type 1 generic Lens culinaris 3864 0.70775 0.707749993 0.707749993 mg/100 g Lettuce Type 1 specific Lactuca sativa 4236 0.0 0.0 0.0 mg/100 g Lingonberry Type 1 specific Vaccinium vitis-idaea 180772 Medlar Type 1 specific Mespilus germanica 36616 0.05 0.050000002 0.050000002 mg/100 g Millet Type 1 specific Panicum miliaceum 4540 Oat Type 1 specific Avena sativa 4498 Oriental wheat Type 1 specific Triticum turanicum 376534 Peach (var.) Type 1 specific Prunus persica var. persica 323852 2.435882 2.435882351 2.435882351 mg/100 g Peanut Type 1 specific Arachis hypogaea 3818 Pear Type 1 specific Pyrus communis 23211 0.005 0.005 0.005 mg/100 g Pepper Type 1 specific Capsicum annuum 4072 0.0 0.0 0.0 mg/100 g Pineapple Type 1 specific Ananas comosus 4615 0.0 0.0 0.0 mg/100 g Pomegranate Type 1 specific Punica granatum 22663 0.16 0.159999996 0.159999996 mg/100 g Quince Type 1 specific Cydonia oblonga 36610 12.203295 29.375385138 0.100000004 mg/100 g Quinoa Type 1 specific Chenopodium quinoa 63459 Red bell pepper Type 1 specific Capsicum annuum 4072 0.0 0.0 0.0 mg/100 g Red rice Type 1 specific Oryza rufipogon 4529 Red tea Type 1 Redcurrant Type 1 specific Ribes rubrum 175228 0.2 0.200000008 0.200000008 mg/100 g Rice Type 1 specific Oryza sativa 4530 Rubus (Blackberry, Raspberry) Type 1 specific Rubus 23216 0.33 0.330000003 0.330000003 mg/100 g Rye Type 1 specific Secale cereale 4550 Sherry Type 2 specific 1.47 1.470000029 1.470000029 mg/100 g Sorghum Type 1 specific Sorghum bicolor 4558 Soy bean Type 1 specific Glycine max 3847 Spelt Type 1 specific Triticum spelta 58933 Strawberry Type 1 specific Fragaria X ananassa 3747 1.1 1.100000064 1.100000064 mg/100 g Sweet cherry Type 1 specific Prunus avium 42229 0.08 0.079999998 0.079999998 mg/100 g Tartary buckwheat Type 1 specific Fagopyrum tataricum 62330 Tea Type 1 specific Camellia sinensis 4442 0.43 0.49000001 0.370000005 mg/100 g Teff Type 1 specific Eragrostis tef 110835 Triticale Type 1 specific X Triticosecale rimpaui Wheat Type 1 specific Triticum 4564 Wild rice Type 1 specific Zizania 15949 Yellow wax bean Type 1 specific Phaseolus vulgaris 3885 0.82 0.820000013 0.820000013 mg/100 g Yellow zucchini Type 1 specific Cucurbita pepo var. cylindrica 0.0 0.0 0.0 mg/100 g Angiotensin converting enzyme inhibitor 18 An EC 3.4.15.* (peptidyl-dipeptidase) inhibitor that interferes with the action of peptidyl-dipeptidase A (EC 3.4.15.1). Anti-oxidant 502 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324. Beta-adrenergic receptor blocker 727 Any agent that acts on an adrenergic receptor or affects the life cycle of an adrenergic transmitter.