| Record Information |
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| Version | 2.0 |
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| Created at | 2022-09-12 14:36:35 UTC |
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| Updated at | 2022-09-12 14:36:36 UTC |
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| NP-MRD ID | NP0329830 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | 3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 3,4,5-trihydroxybenzoate |
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| Description | Beta-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). |
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| Structure | OCC1OC(OC(=O)C2=CC(O)=C(O)C(O)=C2)C(O)C(O)C1O 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 |
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| Synonyms | | Value | Source |
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| b-Glucogallin | Generator | | Β-glucogallin | Generator | | 1-Galloyl-glucose | HMDB | | 1-Galloylglucose | HMDB | | 1-O-(3,4,5-Trihydroxybenzoyl)-beta-D-glucopyranose | HMDB | | 1-O-Galloyl-b-D-glucopyranose | HMDB | | 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 acid | Generator | | 1-Glucosyl gallic acid | Generator | | 1-O-Galloylglucose | MeSH | | Galloylglucose | MeSH | | 1-O-Galloyl-beta-D-glucose | MeSH | | Glucogallin | MeSH |
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| Chemical Formula | C13H16O10 |
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| Average Mass | 332.2601 Da |
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| Monoisotopic Mass | 332.07435 Da |
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| IUPAC Name | 3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 3,4,5-trihydroxybenzoate |
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| Traditional Name | glucogallin |
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| CAS Registry Number | Not Available |
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| SMILES | OCC1OC(OC(=O)C2=CC(O)=C(O)C(O)=C2)C(O)C(O)C1O |
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| 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 |
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| InChI Key | GDVRUDXLQBVIKP-UHFFFAOYSA-N |
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| Experimental Spectra |
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| Not Available | | Predicted Spectra |
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| Not Available | | Chemical Shift Submissions |
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| Not Available | | Species |
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| Species of Origin | |
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| Chemical Taxonomy |
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| 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). |
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| Kingdom | Organic compounds |
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| Super Class | Phenylpropanoids and polyketides |
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| Class | Tannins |
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| Sub Class | Not Available |
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| Direct Parent | Tannins |
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| Alternative Parents | |
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| 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
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| Molecular Framework | Aromatic heteromonocyclic compounds |
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| External Descriptors | |
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| Physical Properties |
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| State | Not Available |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | LogP | Not Available | Not Available |
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| Predicted Properties | |
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