Proanthocyanidin
PubChem CID: 108065
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| Compound Synonyms | Proanthocyanidin, 18206-61-6, Proanthocyanidin A, (3R)-2-(3,5-dihydroxy-4-methoxyphenyl)-8-[(2R,3R,4R)-3,5,7-trihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-chromen-4-yl]-3,4-dihydro-2H-chromene-3,5,7-triol, Ouratea proanthocyanidin A, 274678-42-1, Zangrado, CCRIS 9188, SCHEMBL4747623, AKOS015967674, (4,8'-Bi-2H-1-benzopyran)-3,3',5,5',7,7'-hexol, 2'-(3,5-dihydroxy-4-methoxyphenyl)-3,3',4,4'-tetrahydro-2-(4-hydroxyphenyl)-, (2R-(2alpha,3alpha,4beta(2'R*,3'R*)))-, 2-(3,5-Dihydroxy-4-methoxyphenyl)-8-[3,5,7-trihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-chromen-4-yl]-3,4-dihydro-2H-chromene-3,5,7-triol |
|---|---|
| Ghose Rule | False |
| Classyfire Kingdom | Organic compounds |
| Topological Polar Surface Area | 210.0 |
| Hydrogen Bond Donor Count | 9.0 |
| Pfizer 3 75 Rule | False |
| Scaffold Graph Level | C1CCC(C2CCC3CCCC(C4CC(C5CCCCC5)CC5CCCCC54)C3C2)CC1 |
| Np Classifier Class | Flavan-3-ols, Proanthocyanins |
| Deep Smiles | COccO)cccc6O)))COccC[C@H]6O)))cO)ccc6[C@@H][C@@H]O)[C@H]Occ6cO)ccc6)O)))))))cccccc6))O)))))))))O |
| Heavy Atom Count | 43.0 |
| Classyfire Class | Flavonoids |
| Description | Proanthocyanidins, also known as zangrado or polyhydroxyflavan-3-ol, is a member of the class of compounds known as biflavonoids and polyflavonoids. Biflavonoids and polyflavonoids 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''. Proanthocyanidins is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Proanthocyanidins can be found in a number of food items such as roselle, allspice, cocoa bean, and sweet bay, which makes proanthocyanidins a potential biomarker for the consumption of these food products. Proanthocyanidins were discovered in 1947 by Jacques Masquelier, who developed and patented techniques for the extraction of oligomeric proanthocyanidins from pine bark and grape seeds. Often associated with consumer products made from cranberries, grape seeds or red wine, proanthocyanidins were once proposed as factors inhibiting urinary tract infections in women, but this research has been refuted by expert scientific committees . |
| Scaffold Graph Node Level | C1CCC(C2CC(C3CCCC4CCC(C5CCCCC5)OC43)C3CCCCC3O2)CC1 |
| Classyfire Subclass | Biflavonoids and polyflavonoids |
| Isotope Atom Count | 0.0 |
| Molecular Complexity | 920.0 |
| Database Name | cmaup_ingredients;fooddb_chem_all;hmdb_chem_all;imppat_phytochem;npass_chem_all;pubchem |
| Defined Atom Stereocenter Count | 4.0 |
| Iupac Name | (3R)-2-(3,5-dihydroxy-4-methoxyphenyl)-8-[(2R,3R,4R)-3,5,7-trihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-chromen-4-yl]-3,4-dihydro-2H-chromene-3,5,7-triol |
| Prediction Hob | 0.0 |
| Class | Flavonoids |
| Veber Rule | False |
| Classyfire Superclass | Phenylpropanoids and polyketides |
| Xlogp | 2.7 |
| Superclass | Phenylpropanoids and polyketides |
| Subclass | Biflavonoids and polyflavonoids |
| Gsk 4 400 Rule | False |
| Molecular Formula | C31H28O12 |
| Scaffold Graph Node Bond Level | c1ccc(C2CC(c3cccc4c3OC(c3ccccc3)CC4)c3ccccc3O2)cc1 |
| Prediction Swissadme | 0.0 |
| Inchi Key | JPFCOVZKLAXXOE-XBNSMERZSA-N |
| Silicos It Class | Moderately soluble |
| Fcsp3 | 0.2258064516129032 |
| Logs | -4.674 |
| Rotatable Bond Count | 4.0 |
| Logd | 2.014 |
| Synonyms | Proanthocyanidin, Zangrado, Polyhydroxyflavan-3-ol, Proanthocyanidins, Polymers, anthocyanidin, Procyanidins, Anthocyanidin polymers, Condensed tannin, Condensed tannins, Tannin, condensed, Tannins, condensed, proanthocyandin, proanthocyanidin, proanthocyanidin-a-type, proanthocyanidins |
| Esol Class | Moderately soluble |
| Functional Groups | CO, cO, cOC |
| Compound Name | Proanthocyanidin |
| Kingdom | Organic compounds |
| Prediction Hob Swissadme | 0.0 |
| Exact Mass | 592.158 |
| Formal Charge | 0.0 |
| Monoisotopic Mass | 592.158 |
| Hydrogen Bond Acceptor Count | 12.0 |
| Molecular Weight | 592.5 |
| Gi Absorption | False |
| Covalent Unit Count | 1.0 |
| Total Atom Stereocenter Count | 5.0 |
| Total Bond Stereocenter Count | 0.0 |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Lipinski Rule Of 5 | False |
| Esol | -5.357551855813956 |
| Inchi | InChI=1S/C31H28O12/c1-41-31-20(37)6-13(7-21(31)38)28-22(39)10-16-17(34)11-19(36)25(30(16)43-28)26-24-18(35)8-15(33)9-23(24)42-29(27(26)40)12-2-4-14(32)5-3-12/h2-9,11,22,26-29,32-40H,10H2,1H3/t22-,26-,27-,28?,29-/m1/s1 |
| Smiles | COC1=C(C=C(C=C1O)C2[C@@H](CC3=C(O2)C(=C(C=C3O)O)[C@@H]4[C@H]([C@H](OC5=CC(=CC(=C45)O)O)C6=CC=C(C=C6)O)O)O)O |
| Nring | 6.0 |
| Np Classifier Biosynthetic Pathway | Shikimates and Phenylpropanoids |
| Defined Bond Stereocenter Count | 0.0 |
| Egan Rule | False |
| Taxonomy Direct Parent | Biflavonoids and polyflavonoids |
| Np Classifier Superclass | Flavonoids |
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