AFCDB: 1,2,6-Trigalloyl-beta-D-glucopyranose (FDB018710)

Record Information

Version

1.0

Creation date

2010-04-08 22:13:53 UTC

Update date

2019-11-26 03:16:32 UTC

Primary ID

FDB018710

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

1,2,6-Trigalloyl-beta-D-glucopyranose

Description

1,2,6-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 Number

79886-49-0

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	1.17 g/L	ALOGPS
logP	1.96	ALOGPS
logP	1.82	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	7.63	ChemAxon
pKa (Strongest Basic)	-5.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	11	ChemAxon
Polar Surface Area	310.66 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	143.22 m³·mol⁻¹	ChemAxon
Polarizability	59.2 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Chemical Formula

C27H24O18

IUPAC name

4,5-dihydroxy-2-(3,4,5-trihydroxybenzoyloxy)-6-[(3,4,5-trihydroxybenzoyloxy)methyl]oxan-3-yl 3,4,5-trihydroxybenzoate

InChI Identifier

InChI=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 Key

LLENXGNWVNSBQG-UHFFFAOYSA-N

Isomeric SMILES

OC1C(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 Weight

636.4687

Monoisotopic Molecular Weight

636.096263964

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).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Tannins

Sub Class

Not Available

Direct Parent

Tannins

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 Framework

Aromatic heteromonocyclic compounds

External Descriptors

a hydrolyzable tannin (CPD-8947 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biological:

Plant

Biological location:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Role

Biological role:

Nutrient

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 50.95%; H 3.80%; O 45.25%	DFC
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	[a]20D +10.3 (c, 0.5 in Me2CO)	DFC
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	1,2,6-Trigalloyl-beta-D-glucopyranose, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-014i-0310900000-dc31a476600c836a9cf4	Spectrum
Predicted GC-MS	1,2,6-Trigalloyl-beta-D-glucopyranose, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	1,2,6-Trigalloyl-beta-D-glucopyranose, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	1,2,6-Trigalloyl-beta-D-glucopyranose, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	1,2,6-Trigalloyl-beta-D-glucopyranose, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	1,2,6-Trigalloyl-beta-D-glucopyranose, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	1,2,6-Trigalloyl-beta-D-glucopyranose, TMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	1,2,6-Trigalloyl-beta-D-glucopyranose, TMS_1_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	1,2,6-Trigalloyl-beta-D-glucopyranose, TMS_1_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	1,2,6-Trigalloyl-beta-D-glucopyranose, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	1,2,6-Trigalloyl-beta-D-glucopyranose, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	1,2,6-Trigalloyl-beta-D-glucopyranose, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	1,2,6-Trigalloyl-beta-D-glucopyranose, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	1,2,6-Trigalloyl-beta-D-glucopyranose, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	1,2,6-Trigalloyl-beta-D-glucopyranose, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	1,2,6-Trigalloyl-beta-D-glucopyranose, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	1,2,6-Trigalloyl-beta-D-glucopyranose, TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	1,2,6-Trigalloyl-beta-D-glucopyranose, TMS_2_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	1,2,6-Trigalloyl-beta-D-glucopyranose, TMS_2_10, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	1,2,6-Trigalloyl-beta-D-glucopyranose, TMS_2_11, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	1,2,6-Trigalloyl-beta-D-glucopyranose, TMS_2_12, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	1,2,6-Trigalloyl-beta-D-glucopyranose, TMS_2_13, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	1,2,6-Trigalloyl-beta-D-glucopyranose, TMS_2_14, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	1,2,6-Trigalloyl-beta-D-glucopyranose, TMS_2_15, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	1,2,6-Trigalloyl-beta-D-glucopyranose, TMS_2_16, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014r-0530905000-5ec3a997328b37f7de83	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0gba-0950702000-f7dc769fd4f43bc0cebd	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-0920110000-2c288890a11e51190c97	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014r-0910504000-1ee75d2a4a696230dd37	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0920200000-a14a890a28f2f8c7d5b9	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-0900000000-a3498ec95183d397a6bb	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0000509000-802f8d7308c719d69c67	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00kb-0593814000-409f25036a03cd988ace	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00or-0900010000-4c0811c5ec2def5a95d6	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0gba-0670901000-fc7fa4318856fde81341	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0uy0-0930532000-6fe291ea4fd0fb54b0f9	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fvr-4911111000-bacd5a092ef3232ed990	2021-09-23	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

2603752

ChEMBL ID

Not Available

KEGG Compound ID

C04360

Pubchem Compound ID

3357644

Pubchem Substance ID

Not Available

ChEBI ID

27395

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB39182

CRC / DFC (Dictionary of Food Compounds) ID

LML45-O:LML47-Q

EAFUS ID

Not Available

Dr. Duke ID

1,2,6-TRI-O-GALLOYL-GLUCOSE|1,2,6-TRI-O-GALLOYL-BETA-4C-1-GLUCOPYRANOSE|1,2,6-TRI-O-GALLOYL-BETA-D-GLUCOSE

BIGG ID

Not Available

KNApSAcK ID

C00035453

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
antioxidant	22586	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 blocker	37962	Any agent that acts on an adrenergic receptor or affects the life cycle of an adrenergic transmitter.	DUKE
topoisomerase-II inhibitor	50750	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 inhibitor	35634	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

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).

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

Structure for FDB018710 (1,2,6-Trigalloyl-beta-D-glucopyranose)