Showing Compound Gallic acid 4-glucoside (FDB021732)

Record Information

Version

1.0

Creation date

2011-03-17 23:28:18 UTC

Update date

2019-11-26 03:20:49 UTC

Primary ID

FDB021732

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Gallic acid 4-glucoside

Description

4-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 Number

Not Available

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
3,4,5-Trihydroxybenzoic acid; 4-O-b-D-Glucopyranoside	db_source
3,5-Dihydroxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoate	Generator
4-Glucogallate	Generator
Gallate 4-glucoside	Generator
Gallic acid 4-glucoside	manual
Gallic acid 4-O-glucoside	HMDB

Showing 1 to 6 of 6 entries

Predicted Properties

Property	Value	Source
Water Solubility	20.4 g/L	ALOGPS
logP	-1.1	ALOGPS
logP	-1.5	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	3.88	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	177.14 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	71.4 m³·mol⁻¹	ChemAxon
Polarizability	29.94 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C13H16O10

IUPAC name

3,5-dihydroxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoic acid

InChI Identifier

InChI=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 Key

YPSNWSNUXIIKHO-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 Weight

332.261

Monoisotopic Molecular Weight

332.074346715

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.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Phenolic 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 Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

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

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Gallic acid 4-glucoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0w90-6945000000-c56ba3e373e935ea980e	Spectrum
Predicted GC-MS	Gallic acid 4-glucoside, 5 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-004i-2402019000-e9106a7d4c43eab6a9e2	Spectrum
Predicted GC-MS	Gallic acid 4-glucoside, TBDMS_3_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Gallic acid 4-glucoside, TBDMS_3_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Gallic acid 4-glucoside, TBDMS_4_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Gallic acid 4-glucoside, TBDMS_4_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Gallic acid 4-glucoside, TBDMS_4_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Gallic acid 4-glucoside, TBDMS_4_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Gallic acid 4-glucoside, TBDMS_4_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Gallic acid 4-glucoside, TBDMS_4_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Gallic acid 4-glucoside, TBDMS_4_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Gallic acid 4-glucoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Gallic acid 4-glucoside, "4-Glucogallic acid,3TBDMS,#1" TMS, 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	splash10-00yi-0926000000-06fa15afd446ec061949	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0fk9-0900000000-8b85b9db5996c2d0db24	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fi0-1900000000-67fc4b41b0f3f3d39420	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00lr-1839000000-dd245ed5c1430c69ce09	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-1911000000-1932579114ad502963f3	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01di-3900000000-f7cf955e4f5b91d147d5	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0900000000-4a4f1ff86c40fc391cb2	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ufr-0900000000-3a690ebda3080bcfdae4	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00ds-9620000000-34276312692db2bb9de1	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0319000000-cc2f8daa2f94bb475ce0	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0f89-1932000000-8664792e13f63d93bede	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0104-8900000000-62121b6fdb0174410be5	2021-09-23	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

8263651

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

10088114

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

435

DrugBank ID

Not Available

HMDB ID

HMDB41593

CRC / DFC (Dictionary of Food Compounds) ID

BFL35-I:PZQ09-K

EAFUS ID

Not Available

Dr. Duke ID

GALLIC-ACID-4-O-BETA-D-GLUCOSIDE

BIGG ID

Not Available

KNApSAcK ID

Not Available

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

BFL35-I:GSV53-A

Associated Foods

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

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

— 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).

Showing Compound Gallic acid 4-glucoside (FDB021732)

Structure for FDB021732 (Gallic acid 4-glucoside)