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Record Information
Version2.0
Created at2022-09-12 14:36:35 UTC
Updated at2022-09-12 14:36:36 UTC
NP-MRD IDNP0329830
Secondary Accession NumbersNone
Natural Product Identification
Common Name3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 3,4,5-trihydroxybenzoate
DescriptionBeta-Glucogallin, also known as 1-galloyl-glucose or β-glucogallin, 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). It 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. Half-life of β-Glucogallin in human body seems to be unknown. The molecule is then used by enzymes in the gallotannins synthetis pathway like beta-glucogallin O-galloyltransferase or beta-glucogallin-tetrakisgalloylglucose O-galloyltransferase. Beta-Glucogallin is an extremely weak basic (essentially neutral) compound (based on its pKa). Glucogallin is chemical compound formed from gallic acid and β-D-glucose. Outside of the human body, beta-Glucogallin is found, on average, in the highest concentration within tea. Beta-Glucogallin has also been detected, but not quantified in, green vegetables. This could make beta-glucogallin a potential biomarker for the consumption of these foods. β-Glucogallin is aldose reductase inhibitor. This enzyme can be found in oak leaf preparations. This the first step in the biosynthesis of gallotannins. 3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 3,4,5-trihydroxybenzoate is found in Acalypha indica, Acer rubrum, Arbutus unedo, Elaeocarpus sylvestris, Eucalyptus viminalis, Tetradium glabrifolium, Euphorbia jolkinii, Fagopyrum megacarpum, Lotus corniculatus, Mallotus repandus, Paeonia lactiflora, Pelargonium reniforme, Phyllagathis rotundifolia, Phyllanthus emblica, Phyllanthus niruri, Phyllanthus virgatus, Prunus domestica, Quercus acutissima, Quercus salicina, Rhynchosia volubilis, Sanguisorba minor, Vachellia nilotica and Vachellia tortilis. It can be found in oaks species like the North American white oak (Quercus alba), European red oak (Quercus robur) and Amla fruit (Phyllanthus emblica).
Structure
Thumb
Synonyms
ValueSource
b-GlucogallinGenerator
Β-glucogallinGenerator
1-Galloyl-glucoseHMDB
1-GalloylglucoseHMDB
1-O-(3,4,5-Trihydroxybenzoyl)-beta-D-glucopyranoseHMDB
1-O-Galloyl-b-D-glucopyranoseHMDB
beta-D-Glucopyranose, 1-(3,4,5-trihydroxybenzoate)HMDB
D-Glucose 1-(3,4,5-trihydroxybenzoate)HMDB
3,4,5-Trihydroxy-6-(hydroxymethyl)oxan-2-yl 3,4,5-trihydroxybenzoic acidGenerator
1-Glucosyl gallic acidGenerator
1-O-GalloylglucoseMeSH
GalloylglucoseMeSH
1-O-Galloyl-beta-D-glucoseMeSH
GlucogallinMeSH
Chemical FormulaC13H16O10
Average Mass332.2601 Da
Monoisotopic Mass332.07435 Da
IUPAC Name3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 3,4,5-trihydroxybenzoate
Traditional Nameglucogallin
CAS Registry NumberNot Available
SMILES
OCC1OC(OC(=O)C2=CC(O)=C(O)C(O)=C2)C(O)C(O)C1O
InChI Identifier
InChI=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
InChI KeyGDVRUDXLQBVIKP-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Acalypha indicaLOTUS Database
Acer rubrumLOTUS Database
Arbutus unedoLOTUS Database
Elaeocarpus sylvestrisLOTUS Database
Eucalyptus viminalisLOTUS Database
Euodia fargesiiLOTUS Database
Euphorbia jolkiniLOTUS Database
Fagopyrum megacarpumLOTUS Database
Lotus corniculatusLOTUS Database
Mallotus repandusLOTUS Database
Paeonia lactifloraLOTUS Database
Pelargonium reniformeLOTUS Database
Phyllagathis rotundifoliaLOTUS Database
Phyllanthus emblicaLOTUS Database
Phyllanthus niruriLOTUS Database
Phyllanthus virgatusLOTUS Database
Prunus domesticaLOTUS Database
Quercus acutissimaLOTUS Database
Quercus salicinaLOTUS Database
Rhynchosia volubilisLOTUS Database
Sanguisorba minorLOTUS Database
Vachellia niloticaLOTUS Database
Vachellia tortilisLOTUS Database
Chemical Taxonomy
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
  • Hexose monosaccharide
  • Gallic acid or derivatives
  • P-hydroxybenzoic acid alkyl ester
  • M-hydroxybenzoic acid ester
  • P-hydroxybenzoic acid ester
  • Benzoate ester
  • Benzenetriol
  • Benzoic acid or derivatives
  • Pyrogallol derivative
  • Benzoyl
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monosaccharide
  • Monocyclic benzene moiety
  • Benzenoid
  • Oxane
  • Secondary alcohol
  • Carboxylic acid ester
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Polyol
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Organic oxygen compound
  • Primary alcohol
  • Organic oxide
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Polarizability30.69 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0038728
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB018137
KNApSAcK IDNot Available
Chemspider ID3818711
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkGlucogallin
METLIN IDNot Available
PubChem Compound4628122
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]