Canmetcon
Record Information
Version1.0
Creation date2010-04-08 22:04:29 UTC
Update date2018-05-28 23:01:16 UTC
Primary IDFDB000233
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameGalloyl glucose
DescriptionGalloyl glucose, also known as 1-galloyl-beta-D-glucose or beta-glucogallin, is a member of the class of compounds known as tannins. Tannins 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). Galloyl glucose is soluble (in water) and a very weakly acidic compound (based on its pKa). Galloyl glucose can be found in a number of food items such as pomegranate, strawberry, redcurrant, and rubus (blackberry, raspberry), which makes galloyl glucose a potential biomarker for the consumption of these food products. Galloyl glucose is formed by a gallate 1-beta-glucosyltransferase (UDP-glucose: gallate glucosyltransferase), an enzyme performing the esterification of two substrates, UDP-glucose and gallate to yield two products, UDP and glucogallin. This enzyme can be found in oak leaf preparations .
CAS NumberNot Available
Structure
Thumb
Synonyms
SynonymSource
1-Galloyl-beta-D-glucoseChEBI
1-Galloyl-beta-glucoseChEBI
beta-GlucogallinChEBI
1-Galloyl-b-D-glucoseGenerator
1-Galloyl-β-D-glucoseGenerator
1-O-Galloyl-b-D-glucoseGenerator
1-O-Galloyl-β-D-glucoseGenerator
1-Galloyl-b-glucoseGenerator
1-Galloyl-β-glucoseGenerator
b-GlucogallinGenerator
β-glucogallinGenerator
Predicted Properties
PropertyValueSource
Water Solubility22.1 g/LALOGPS
logP-1.3ALOGPS
logP-1.3ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)8.08ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area177.14 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity71.69 m³·mol⁻¹ChemAxon
Polarizability29.83 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC13H16O10
IUPAC name(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 3,4,5-trihydroxybenzoate
InChI IdentifierInChI=1S/C13H16O10/c14-3-7-9(18)10(19)11(20)13(22-7)23-12(21)4-1-5(15)8(17)6(16)2-4/h1-2,7,9-11,13-20H,3H2/t7-,9-,10+,11-,13+/m1/s1
InChI KeyGDVRUDXLQBVIKP-HQHREHCSSA-N
Isomeric SMILESOC[C@H]1O[C@@H](OC(=O)C2=CC(O)=C(O)C(O)=C2)[C@H](O)[C@@H](O)[C@@H]1O
Average Molecular Weight332.2601
Monoisotopic Molecular Weight332.074346732
Classification
DescriptionThis compound belongs to the class of organic compounds known as tannins. These are naturally occurring polyphenols which be categorized into four main classes
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassTannins
Sub ClassNot Available
Direct ParentTannins
Alternative Parents
Substituents
  • Tannin
  • Galloyl ester
  • Gallic acid or derivatives
  • Benzoate ester
  • Pyrogallol derivative
  • Benzoic acid or derivatives
  • Benzenetriol
  • 1,2-diphenol
  • Benzoyl
  • Phenol
  • Benzenoid
  • Oxane
  • Monosaccharide
  • Saccharide
  • Monocyclic benzene moiety
  • Secondary alcohol
  • Polyol
  • Carboxylic acid ester
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Acetal
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
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
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-9623000000-beca8f27fef9fce8f078View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fk9-0902000000-0c84b6c8e74dfd13d3a2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-03973e83a0db08c1b5a5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ufr-2900000000-4cad2ae123289e57d139View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0gc0-1904000000-f28c95d9eb0300138627View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-02t9-2901000000-9b510243388f6158b7cbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-016u-7900000000-21d7773cb744645d8c25View in MoNA
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC01158
Pubchem Compound ID124375
Pubchem Substance IDNot Available
ChEBI ID15834
Phenol-Explorer ID444
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDGALLOYLGLUCOSE
BIGG IDNot Available
KNApSAcK IDC00002652
HET 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
dehydrogenase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.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— 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).