2,3-Hexahydroxydiphenoylglucopyranose (CHEM034705)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:08:42 UTC
Update Date2016-11-09 01:21:10 UTC
Accession NumberCHEM034705
Identification
Common Name2,3-Hexahydroxydiphenoylglucopyranose
ClassSmall Molecule
Description3,4,5,11,14,20,21,22-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.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
SynonymsNot Available
Chemical FormulaC20H18O14
Average Molecular Mass482.349 g/mol
Monoisotopic Mass482.070 g/mol
CAS Registry NumberNot Available
IUPAC Name3,4,5,11,14,20,21,22-octahydroxy-13-(hydroxymethyl)-9,12,16-trioxatetracyclo[16.4.0.0^{2,7}.0^{10,15}]docosa-1(22),2,4,6,18,20-hexaene-8,17-dione
Traditional Name3,4,5,11,14,20,21,22-octahydroxy-13-(hydroxymethyl)-9,12,16-trioxatetracyclo[16.4.0.0^{2,7}.0^{10,15}]docosa-1(22),2,4,6,18,20-hexaene-8,17-dione
SMILESOCC1OC(O)C2OC(=O)C3=C(C(O)=C(O)C(O)=C3)C3=C(O)C(O)=C(O)C=C3C(=O)OC2C1O
InChI IdentifierInChI=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
InChI KeyGEAGRKQCZVLNAU-UHFFFAOYSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassTannins
Sub ClassHydrolyzable tannins
Direct ParentHydrolyzable tannins
Alternative Parents
Substituents
  • Hydrolyzable tannin
  • Gallic acid or derivatives
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Dicarboxylic acid or derivatives
  • Monosaccharide
  • Oxane
  • Benzenoid
  • Secondary alcohol
  • Lactone
  • Hemiacetal
  • Carboxylic acid ester
  • Polyol
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Oxacycle
  • Primary alcohol
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility10.5 g/LALOGPS
logP0.53ALOGPS
logP-0.49ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)7.5ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area243.9 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity106.53 m³·mol⁻¹ChemAxon
Polarizability42.85 ųChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-001i-8910448000-95b5138fa3ade767e886Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-116u-9001700000-b750c1d95c4ea2172757Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000900000-ba81afc576acd94fc414Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0159-1000900000-214d3dad2bf5c10d472bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0007-9107600000-21e52359e15c15091120Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0000900000-4c1c811abe22b4296f45Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-08gi-3002900000-c601ae8503f5027371aeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01ox-9004400000-af236d69b31e54453ad8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00lr-0000900000-57fd8e663e397d3b2468Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001l-0002900000-bf340542d4e5f6c1e09dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00fv-9008500000-b79b78d136eca9202c41Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0000900000-1b56249743c8dbe3d13eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01po-1004900000-42d1bc5f427000ffed44Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-6009300000-787fa4af2a19a20cfbcaSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0137009
FooDB IDFDB021698
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID430987
ChEBI IDNot Available
PubChem Compound ID492390
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Cheminformatics Tools for Enabling Metabolomics, 2017 (PhD thesis)