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Showing Compound 1,2,6-Trigalloyl-beta-D-glucopyranose (FDB018710)

Record Information
Version1.0
Creation date2010-04-08 22:13:53 UTC
Update date2019-11-26 03:16:32 UTC
Primary IDFDB018710
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name1,2,6-Trigalloyl-beta-D-glucopyranose
Description1,2,6-Trigalloyl-beta-D-glucopyranose belongs to the class of organic compounds known as tannins. These are naturally occurring polyphenols which be categorized into four main classes: hydrolyzable tannin (based on ellagic acid or gallic acid), condensed tannins (made of oligomeric or polymeric proanthocyanidins), complex tannins (made of a catechin bound to a gallotannin or elagitannin), and phlorotannins (oligomers of phloroglucinol). 1,2,6-Trigalloyl-beta-D-glucopyranose has been detected, but not quantified in, several different foods, such as fruits, garden rhubarbs (Rheum rhabarbarum), pomegranates (Punica granatum), and red raspberries (Rubus idaeus). This could make 1,2,6-trigalloyl-beta-D-glucopyranose a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 1,2,6-Trigalloyl-beta-D-glucopyranose.
CAS Number79886-49-0
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
1,2,6-Trigalloyl-b-D-glucopyranoseGenerator
1,2,6-Trigalloyl-β-D-glucopyranoseGenerator
1,2,6-Tri-O-galloyl-beta-D-glucoseHMDB
1-O,2-O,6-O-Trigalloyl-beta-D-glucoseHMDB
beta-D-Glucopyranose, 1,2,6-tris(3,4,5-trihydroxybenzoate)HMDB
[3,4-Dihydroxy-5,6-bis(3,4,5-trihydroxybenzoyloxy)oxan-2-yl]methyl 3,4,5-trihydroxybenzoic acidGenerator
1,2,6-tri-O-Galloyl-beta-D-glucosebiospider
Predicted Properties
PropertyValueSource
Water Solubility1.17 g/LALOGPS
logP1.96ALOGPS
logP1.82ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)7.63ChemAxon
pKa (Strongest Basic)-5.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area310.66 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity143.22 m³·mol⁻¹ChemAxon
Polarizability59.2 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC27H24O18
IUPAC name4,5-dihydroxy-2-(3,4,5-trihydroxybenzoyloxy)-6-[(3,4,5-trihydroxybenzoyloxy)methyl]oxan-3-yl 3,4,5-trihydroxybenzoate
InChI IdentifierInChI=1S/C27H24O18/c28-11-1-8(2-12(29)18(11)34)24(39)42-7-17-21(37)22(38)23(44-25(40)9-3-13(30)19(35)14(31)4-9)27(43-17)45-26(41)10-5-15(32)20(36)16(33)6-10/h1-6,17,21-23,27-38H,7H2
InChI KeyLLENXGNWVNSBQG-UHFFFAOYSA-N
Isomeric SMILESOC1C(O)C(OC(=O)C2=CC(O)=C(O)C(O)=C2)C(OC(=O)C2=CC(O)=C(O)C(O)=C2)OC1COC(=O)C1=CC(O)=C(O)C(O)=C1
Average Molecular Weight636.4687
Monoisotopic Molecular Weight636.096263964
Classification
Description Belongs to the class of organic compounds known as tannins. These are naturally occurring polyphenols which be categorized into four main classes: Hydrolyzable tannin (based on ellagic acid or gallic acid), condensed tannins (made of oligomeric or polymeric proanthocyanidins), complex tannins (made of a catechin bound to a gallotannin or elagitannin), and phlorotannins (oligomers of phloroglucinol).
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassTannins
Sub ClassNot Available
Direct ParentTannins
Alternative Parents
Substituents
  • Tannin
  • Galloyl ester
  • Gallic acid or derivatives
  • P-hydroxybenzoic acid alkyl ester
  • M-hydroxybenzoic acid ester
  • P-hydroxybenzoic acid ester
  • Benzoate ester
  • Benzenetriol
  • Benzoic acid or derivatives
  • Tricarboxylic acid or derivatives
  • Pyrogallol derivative
  • Benzoyl
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monosaccharide
  • Oxane
  • Monocyclic benzene moiety
  • Benzenoid
  • Carboxylic acid ester
  • 1,2-diol
  • Secondary alcohol
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Alcohol
  • Organic oxide
  • Organooxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 50.95%; H 3.80%; O 45.25%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]20D +10.3 (c, 0.5 in Me2CO)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS1,2,6-Trigalloyl-beta-D-glucopyranose, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-014i-0310900000-dc31a476600c836a9cf4Spectrum
Predicted GC-MS1,2,6-Trigalloyl-beta-D-glucopyranose, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS1,2,6-Trigalloyl-beta-D-glucopyranose, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS1,2,6-Trigalloyl-beta-D-glucopyranose, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS1,2,6-Trigalloyl-beta-D-glucopyranose, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS1,2,6-Trigalloyl-beta-D-glucopyranose, TMS_1_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS1,2,6-Trigalloyl-beta-D-glucopyranose, TMS_1_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS1,2,6-Trigalloyl-beta-D-glucopyranose, TMS_1_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS1,2,6-Trigalloyl-beta-D-glucopyranose, TMS_1_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS1,2,6-Trigalloyl-beta-D-glucopyranose, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS1,2,6-Trigalloyl-beta-D-glucopyranose, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS1,2,6-Trigalloyl-beta-D-glucopyranose, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS1,2,6-Trigalloyl-beta-D-glucopyranose, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS1,2,6-Trigalloyl-beta-D-glucopyranose, TMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS1,2,6-Trigalloyl-beta-D-glucopyranose, TMS_2_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS1,2,6-Trigalloyl-beta-D-glucopyranose, TMS_2_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS1,2,6-Trigalloyl-beta-D-glucopyranose, TMS_2_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS1,2,6-Trigalloyl-beta-D-glucopyranose, TMS_2_9, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS1,2,6-Trigalloyl-beta-D-glucopyranose, TMS_2_10, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS1,2,6-Trigalloyl-beta-D-glucopyranose, TMS_2_11, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS1,2,6-Trigalloyl-beta-D-glucopyranose, TMS_2_12, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS1,2,6-Trigalloyl-beta-D-glucopyranose, TMS_2_13, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS1,2,6-Trigalloyl-beta-D-glucopyranose, TMS_2_14, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS1,2,6-Trigalloyl-beta-D-glucopyranose, TMS_2_15, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS1,2,6-Trigalloyl-beta-D-glucopyranose, TMS_2_16, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014r-0530905000-5ec3a997328b37f7de832016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gba-0950702000-f7dc769fd4f43bc0cebd2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0920110000-2c288890a11e51190c972016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014r-0910504000-1ee75d2a4a696230dd372016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0920200000-a14a890a28f2f8c7d5b92016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-0900000000-a3498ec95183d397a6bb2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000509000-802f8d7308c719d69c672021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kb-0593814000-409f25036a03cd988ace2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00or-0900010000-4c0811c5ec2def5a95d62021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gba-0670901000-fc7fa4318856fde813412021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uy0-0930532000-6fe291ea4fd0fb54b0f92021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fvr-4911111000-bacd5a092ef3232ed9902021-09-23View Spectrum
NMRNot Available
ChemSpider ID2603752
ChEMBL IDNot Available
KEGG Compound IDC04360
Pubchem Compound ID3357644
Pubchem Substance IDNot Available
ChEBI ID27395
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB39182
CRC / DFC (Dictionary of Food Compounds) IDLML45-O:LML47-Q
EAFUS IDNot Available
Dr. Duke ID1,2,6-TRI-O-GALLOYL-GLUCOSE|1,2,6-TRI-O-GALLOYL-BETA-4C-1-GLUCOPYRANOSE|1,2,6-TRI-O-GALLOYL-BETA-D-GLUCOSE
BIGG IDNot Available
KNApSAcK IDC00035453
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
antioxidant22586 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.DUKE
beta-adrenergic receptor blocker37962 Any agent that acts on an adrenergic receptor or affects the life cycle of an adrenergic transmitter.DUKE
topoisomerase-II inhibitor50750 A topoisomerase inhibitor that inhibits DNA topoisomerase (ATP-hydrolysing), EC 5.99.1.3 (topoisomerase II), which catalyses ATP-dependent breakage of both strands of DNA, passage of the unbroken strands through the breaks, and rejoining of the broken strands.DUKE
xanthine oxidase inhibitor35634 An EC 1.17.3.* (oxidoreductase acting on CH or CH2 with oxygen as acceptor) inhibitor that interferes with the action of xanthine oxidase (EC 1.17.3.2).DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).