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2,3-(S)-hexahydroxydiphenoyl-D-glucose

PubChem CID: 492390

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Compound Synonyms 2,3-(S)-hexahydroxydiphenoyl-D-glucose, octahydroxy(hydroxymethyl)[?]dione, Q4596756, 2,3,4,5,6,7,11,14-Octahydroxy-13-(hydroxymethyl)-10a,13,14,14a-tetrahydro-11H-dibenzo[f,h]pyrano[3,4-b][1,4]dioxecin-9,16-dione
Ghose Rule False
Classyfire Kingdom Organic compounds
Topological Polar Surface Area 244.0
Hydrogen Bond Donor Count 9.0
Pfizer 3 75 Rule True
Scaffold Graph Level CC1CC2CCCCC2CC(C)C2CCCCC2C2CCCCC12
Np Classifier Class Gallotannins
Deep Smiles OCCOCO)CCC6O))OC=O)cccO)ccc6-ccC=O)O%14))ccO)cc6O))O)))))))O))O
Heavy Atom Count 34.0
Classyfire Class Tannins
Description 3,4,5,11,14,20,21,22-octahydroxy-13-(hydroxymethyl)-9,12,16-trioxatetracyclo[16.4.0.0²,⁷.0¹⁰,¹⁵]docosa-1(22),2,4,6,18,20-hexaene-8,17-dione 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. 3,4,5,11,14,20,21,22-octahydroxy-13-(hydroxymethyl)-9,12,16-trioxatetracyclo[16.4.0.0²,⁷.0¹⁰,¹⁵]docosa-1(22),2,4,6,18,20-hexaene-8,17-dione is soluble (in water) and a very weakly acidic compound (based on its pKa). 3,4,5,11,14,20,21,22-octahydroxy-13-(hydroxymethyl)-9,12,16-trioxatetracyclo[16.4.0.0²,⁷.0¹⁰,¹⁵]docosa-1(22),2,4,6,18,20-hexaene-8,17-dione can be found in pomegranate, which makes 3,4,5,11,14,20,21,22-octahydroxy-13-(hydroxymethyl)-9,12,16-trioxatetracyclo[16.4.0.0²,⁷.0¹⁰,¹⁵]docosa-1(22),2,4,6,18,20-hexaene-8,17-dione a potential biomarker for the consumption of this food product.
Scaffold Graph Node Level OC1OC2CCOCC2OC(O)C2CCCCC2C2CCCCC12
Classyfire Subclass Hydrolyzable tannins
Isotope Atom Count 0.0
Molecular Complexity 778.0
Database Name cmaup_ingredients;fooddb_chem_all;imppat_phytochem;pubchem
Defined Atom Stereocenter Count 0.0
Iupac Name 3,4,5,11,14,20,21,22-octahydroxy-13-(hydroxymethyl)-9,12,16-trioxatetracyclo[16.4.0.02,7.010,15]docosa-1(22),2,4,6,18,20-hexaene-8,17-dione
Prediction Hob 0.0
Veber Rule False
Classyfire Superclass Phenylpropanoids and polyketides
Xlogp -0.6
Gsk 4 400 Rule False
Molecular Formula C20H18O14
Scaffold Graph Node Bond Level O=C1OC2CCOCC2OC(=O)c2ccccc2-c2ccccc21
Prediction Swissadme 0.0
Inchi Key GEAGRKQCZVLNAU-UHFFFAOYSA-N
Silicos It Class Soluble
Fcsp3 0.3
Rotatable Bond Count 1.0
Synonyms 2,3-Hexahydroxydiphenoylglucopyranose, 2,3(s)-hhdp-6-o-galloyl-d-glucose, 4,6-hexahydroxydiphenoyl glucose
Esol Class Soluble
Functional Groups CO, COC(C)O, cC(=O)OC, cO
Compound Name 2,3-(S)-hexahydroxydiphenoyl-D-glucose
Prediction Hob Swissadme 0.0
Exact Mass 482.07
Formal Charge 0.0
Monoisotopic Mass 482.07
Hydrogen Bond Acceptor Count 14.0
Molecular Weight 482.3
Gi Absorption False
Covalent Unit Count 1.0
Total Atom Stereocenter Count 5.0
Total Bond Stereocenter Count 0.0
Lipinski Rule Of 5 False
Esol -2.679246470588237
Inchi InChI=1S/C20H18O14/c21-3-8-13(26)16-17(20(31)32-8)34-19(30)5-2-7(23)12(25)15(28)10(5)9-4(18(29)33-16)1-6(22)11(24)14(9)27/h1-2,8,13,16-17,20-28,31H,3H2
Smiles C1=C2C(=C(C(=C1O)O)O)C3=C(C(=C(C=C3C(=O)OC4C(C(C(OC4O)CO)O)OC2=O)O)O)O
Np Classifier Biosynthetic Pathway Shikimates and Phenylpropanoids
Defined Bond Stereocenter Count 0.0
Egan Rule False
Np Classifier Superclass Phenolic acids (C6-C1)

  • 1. Outgoing r'ship FOUND_IN to/from Punica Granatum (Plant) Rel Props:Source_db:cmaup_ingredients;fooddb_chem_all
  • 2. Outgoing r'ship FOUND_IN to/from Syzygium Cumini (Plant) Rel Props:Reference:ISBN:9788171360536; ISBN:9788172361150
  • 3. Outgoing r'ship FOUND_IN to/from Terminalia Arjuna (Plant) Rel Props:Reference:https://doi.org/10.15482/usda.adc/1239279