Vanilloyl glucose (CHEM025678)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 22:32:34 UTC
Update Date2016-11-09 01:18:08 UTC
Accession NumberCHEM025678
Identification
Common NameVanilloyl glucose
ClassSmall Molecule
DescriptionAn O-acyl carbohydrate that is beta-D-glucose bearing a vanilloyl substituent at position 1.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-O-(4-Hydroxy-3-methoxybenzoyl)-beta-D-glucoseChEBI
1-O-(4-Hydroxy-3-methoxybenzoyl)-b-D-glucoseGenerator
1-O-(4-Hydroxy-3-methoxybenzoyl)-β-D-glucoseGenerator
1-O-Vanilloyl-b-D-glucoseGenerator
1-O-Vanilloyl-β-D-glucoseGenerator
Chemical FormulaC14H18O9
Average Molecular Mass330.289 g/mol
Monoisotopic Mass330.095 g/mol
CAS Registry NumberNot Available
IUPAC Name(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 4-hydroxy-3-methoxybenzoate
Traditional Name(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 4-hydroxy-3-methoxybenzoate
SMILES[H][C@]1(CO)O[C@@]([H])(OC(=O)C2=CC(OC)=C(O)C=C2)[C@]([H])(O)[C@@]([H])(O)[C@]1([H])O
InChI IdentifierInChI=1S/C14H18O9/c1-21-8-4-6(2-3-7(8)16)13(20)23-14-12(19)11(18)10(17)9(5-15)22-14/h2-4,9-12,14-19H,5H2,1H3/t9-,10-,11+,12-,14+/m1/s1
InChI KeyYROOZUQRTLHXIO-DIACKHNESA-N
Chemical Taxonomy
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
  • Hexose monosaccharide
  • P-hydroxybenzoic acid alkyl ester
  • P-hydroxybenzoic acid ester
  • M-methoxybenzoic acid or derivatives
  • Benzoate ester
  • Methoxyphenol
  • Benzoic acid or derivatives
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Benzoyl
  • Phenol ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Oxane
  • Monosaccharide
  • Carboxylic acid ester
  • Secondary alcohol
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Polyol
  • Ether
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Primary alcohol
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility14.3 g/LALOGPS
logP-0.99ALOGPS
logP-0.9ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)8.96ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area145.91 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity74.19 m³·mol⁻¹ChemAxon
Polarizability30.83 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0i00-0902000000-f9374f5d535848e52fc7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-b46505720ecda42c7546Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-3900000000-489521303efb861f56ffSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-016s-1904000000-efbe575ddff28bd54d12Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0i6r-2901000000-e86412263b80389cb893Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0gi3-7900000000-11614dfb4cd58ab8cdeaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fb9-0900000000-6601edabe397e50bed63Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fk9-0910000000-9902340a55f3fe83f723Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0umi-6910000000-ab998840918c25a38808Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0902000000-1f408ff56427a5f3bdc6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ktr-1910000000-7468c35b24d4fbe27212Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pb9-4900000000-9fdaf8c5e4731311864eSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0302470
FooDB IDFDB004689
Phenol Explorer IDNot Available
KNApSAcK IDC00058178
BiGG IDNot Available
BioCyc IDCPD-15006
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID28533627
ChEBI ID71512
PubChem Compound IDNot Available
Kegg Compound IDC20470
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available