Record Information
Version1.0
Creation date2010-04-08 22:09:56 UTC
Update date2019-11-26 03:05:57 UTC
Primary IDFDB012010
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameGlucosyringic acid
DescriptionGlucosyringic 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 Number33228-65-8
Structure
Thumb
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility9.1 g/LALOGPS
logP-0.86ALOGPS
logP-1.3ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)3.87ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area155.14 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity80.37 m³·mol⁻¹ChemAxon
Polarizability34 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC15H20O10
IUPAC name3,5-dimethoxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoic acid
InChI IdentifierInChI=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 KeyBLKMDORKRDACEI-UHFFFAOYSA-N
Isomeric SMILESCOC1=CC(=CC(OC)=C1OC1OC(CO)C(O)C(O)C1O)C(O)=O
Average Molecular Weight360.3133
Monoisotopic Molecular Weight360.10564686
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.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassTannins
Sub ClassHydrolyzable tannins
Direct ParentHydrolyzable 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 FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4j-1619000000-017e226a19fcdd9712b62016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0912000000-350194f74f159801533a2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001j-2900000000-3601c8a4996d847507bf2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0aor-0009000000-2f04ca08d1e8960708aa2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052b-2489000000-0b9f2136b8e462a375aa2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0bu1-3910000000-785afdaefbd4218d0daa2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ow-0819000000-475d20183392dbe2ace42016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000t-0901000000-eb9db5011e6561aa0d562016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001j-1900000000-dbdd8a277b1af149077f2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-8b3684a1f6a94f3a2f912021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f6t-0901000000-1865c7664f6626e810e32021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0015-7931000000-6605404bf3cef0098b732021-10-21View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID5317726
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDBFL35-I:HCM54-L
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00033008
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FennelExpected but not quantifiedNot AvailableKNAPSACK
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Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.