Showing Compound Glucosyringic acid (FDB012010)

Record Information

Version

1.0

Creation date

2010-04-08 22:09:56 UTC

Update date

2019-11-26 03:05:57 UTC

Primary ID

FDB012010

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Glucosyringic acid

Description

Glucosyringic acid, also known as glucosyringate, is a member of the class of compounds known as hydrolyzable tannins. Hydrolyzable tannins are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit. Glucosyringic acid is slightly soluble (in water) and a weakly acidic compound (based on its pKa). Glucosyringic acid can be found in fennel, which makes glucosyringic acid a potential biomarker for the consumption of this food product.

CAS Number

33228-65-8

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

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Synonym	Source
Benzoic acid, 4-(beta-D-glucopyranosyloxy)-3,5-dimethoxy-	biospider
Gluco-syringic acid	biospider
Glucosyringate	Generator
Glucosyringic acid	db_source
Syringate-4-b-D-glucopyranoside	Generator
Syringate-4-beta-D-glucopyranoside	Generator
Syringate-4-β-D-glucopyranoside	Generator
Syringic acid-4-b-D-glucopyranoside	Generator
Syringic acid-4-β-D-glucopyranoside	Generator
Syringin 4-O-beta-glucoside	biospider

Showing 1 to 10 of 10 entries

Predicted Properties

Property	Value	Source
Water Solubility	9.1 g/L	ALOGPS
logP	-0.86	ALOGPS
logP	-1.3	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	3.87	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	155.14 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	80.37 m³·mol⁻¹	ChemAxon
Polarizability	34 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C15H20O10

IUPAC name

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

InChI Identifier

InChI=1S/C15H20O10/c1-22-7-3-6(14(20)21)4-8(23-2)13(7)25-15-12(19)11(18)10(17)9(5-16)24-15/h3-4,9-12,15-19H,5H2,1-2H3,(H,20,21)

InChI Key

BLKMDORKRDACEI-UHFFFAOYSA-N

Isomeric SMILES

COC1=CC(=CC(OC)=C1OC1OC(CO)C(O)C(O)C1O)C(O)=O

Average Molecular Weight

360.3133

Monoisotopic Molecular Weight

360.10564686

Classification

Description

Belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Tannins

Sub Class

Hydrolyzable tannins

Direct Parent

Hydrolyzable tannins

Alternative Parents

Substituents

Hydrolyzable tannin
Phenolic glycoside
Hexose monosaccharide
Gallic acid or derivatives
M-methoxybenzoic acid or derivatives
O-glycosyl compound
Glycosyl compound
M-dimethoxybenzene
Dimethoxybenzene
Benzoic acid or derivatives
Benzoic acid
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Benzoyl
Alkyl aryl ether
Sugar acid
Oxane
Monosaccharide
Benzenoid
Monocyclic benzene moiety
Secondary alcohol
Acetal
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Carboxylic acid
Ether
Polyol
Monocarboxylic acid or derivatives
Primary alcohol
Organic oxide
Hydrocarbon derivative
Alcohol
Organooxygen compound
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

No ontology term

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	C 50.00%; H 5.59%; O 44.40%	DFC
Melting Point	Mp 206-207°	DFC
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Not Available

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4j-1619000000-017e226a19fcdd9712b6	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0912000000-350194f74f159801533a	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001j-2900000000-3601c8a4996d847507bf	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0aor-0009000000-2f04ca08d1e8960708aa	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-052b-2489000000-0b9f2136b8e462a375aa	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0bu1-3910000000-785afdaefbd4218d0daa	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01ow-0819000000-475d20183392dbe2ace4	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000t-0901000000-eb9db5011e6561aa0d56	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001j-1900000000-dbdd8a277b1af149077f	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0900000000-8b3684a1f6a94f3a2f91	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0f6t-0901000000-1865c7664f6626e810e3	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0015-7931000000-6605404bf3cef0098b73	2021-10-21	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

5317726

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

BFL35-I:HCM54-L

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

C00033008

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

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Food	Content Range	Average	Reference

Fennel	Expected but not quantified	Not Available	KNAPSACK

Showing 1 to 1 of 1 entries

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

— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.

Showing Compound Glucosyringic acid (FDB012010)

Structure for FDB012010 (Glucosyringic acid)