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Showing Compound Gallic acid 4-glucoside (FDB021732)

Record Information
Version1.0
Creation date2011-03-17 23:28:18 UTC
Update date2019-11-26 03:20:49 UTC
Primary IDFDB021732
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameGallic acid 4-glucoside
Description4-Glucogallic acid, also known as 4-glucogallate, belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. 4-Glucogallic acid is found, on average, in the highest concentration within highbush blueberries (Vaccinium corymbosum) and blackcurrants (Ribes nigrum). 4-Glucogallic acid has also been detected, but not quantified in, several different foods, such as gooseberries (Ribes uva-crispa), jostaberries (Ribes × nidigrolaria), redcurrants (Ribes rubrum), rubus (blackberry, raspberry), and strawberries (Fragaria X ananassa). This could make 4-glucogallic acid a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 4-Glucogallic acid.
CAS NumberNot Available
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
4-GlucogallateGenerator
Gallic acid 4-O-glucosideHMDB
3,5-Dihydroxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoateGenerator
Gallate 4-glucosideGenerator
3,4,5-Trihydroxybenzoic acid; 4-O-b-D-Glucopyranosidedb_source
Gallic acid 4-glucosidemanual
Predicted Properties
PropertyValueSource
Water Solubility20.4 g/LALOGPS
logP-1.1ALOGPS
logP-1.5ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)3.88ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area177.14 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity71.4 m³·mol⁻¹ChemAxon
Polarizability29.94 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC13H16O10
IUPAC name3,5-dihydroxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoic acid
InChI IdentifierInChI=1S/C13H16O10/c14-3-7-8(17)9(18)10(19)13(22-7)23-11-5(15)1-4(12(20)21)2-6(11)16/h1-2,7-10,13-19H,3H2,(H,20,21)/t7-,8-,9+,10-,13+/m1/s1
InChI KeyYPSNWSNUXIIKHO-YANYRWCTSA-N
Isomeric SMILES[H][C@]1(CO)O[C@@]([H])(OC2=C(O)C=C(C=C2O)C(O)=O)[C@]([H])(O)[C@@]([H])(O)[C@]1([H])O
Average Molecular Weight332.261
Monoisotopic Molecular Weight332.074346715
Classification
Description Belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentPhenolic glycosides
Alternative Parents
Substituents
  • Phenolic glycoside
  • Hexose monosaccharide
  • Gallic acid or derivatives
  • O-glycosyl compound
  • Hydroxybenzoic acid
  • Benzoic acid or derivatives
  • Benzoic acid
  • Phenoxy compound
  • Phenol ether
  • Benzoyl
  • Resorcinol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Sugar acid
  • Monocyclic benzene moiety
  • Monosaccharide
  • Benzenoid
  • Oxane
  • Secondary alcohol
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Polyol
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSGallic acid 4-glucoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0w90-6945000000-c56ba3e373e935ea980eSpectrum
Predicted GC-MSGallic acid 4-glucoside, 5 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-004i-2402019000-e9106a7d4c43eab6a9e2Spectrum
Predicted GC-MSGallic acid 4-glucoside, TBDMS_3_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGallic acid 4-glucoside, TBDMS_3_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGallic acid 4-glucoside, TBDMS_4_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGallic acid 4-glucoside, TBDMS_4_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGallic acid 4-glucoside, TBDMS_4_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGallic acid 4-glucoside, TBDMS_4_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGallic acid 4-glucoside, TBDMS_4_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGallic acid 4-glucoside, TBDMS_4_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGallic acid 4-glucoside, TBDMS_4_9, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGallic acid 4-glucoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGallic acid 4-glucoside, "4-Glucogallic acid,3TBDMS,#1" TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00yi-0926000000-06fa15afd446ec061949Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fk9-0900000000-8b85b9db5996c2d0db24Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fi0-1900000000-67fc4b41b0f3f3d39420Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00lr-1839000000-dd245ed5c1430c69ce09Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-1911000000-1932579114ad502963f3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01di-3900000000-f7cf955e4f5b91d147d5Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-4a4f1ff86c40fc391cb2Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ufr-0900000000-3a690ebda3080bcfdae4Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00ds-9620000000-34276312692db2bb9de1Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0319000000-cc2f8daa2f94bb475ce0Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f89-1932000000-8664792e13f63d93bedeSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0104-8900000000-62121b6fdb0174410be5Spectrum
NMRNot Available
ChemSpider ID8263651
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID10088114
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID435
DrugBank IDNot Available
HMDB IDHMDB41593
CRC / DFC (Dictionary of Food Compounds) IDBFL35-I:PZQ09-K
EAFUS IDNot Available
Dr. Duke IDGALLIC-ACID-4-O-BETA-D-GLUCOSIDE
BIGG IDNot Available
KNApSAcK IDNot Available
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 IDSBFL35-I:GSV53-A
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).