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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2021-09-22 16:36:16 UTC
Update Date2021-09-22 16:36:16 UTC
HMDB IDHMDB0301717
Secondary Accession NumbersNone
Metabolite Identification
Common NameFerulic acid 4-glucoside
DescriptionFerulic acid 4-glucoside is a member of the class of compounds known as phenolic glycosides. Phenolic glycosides 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. Ferulic acid 4-glucoside is slightly soluble (in water) and a weakly acidic compound (based on its pKa). Ferulic acid 4-glucoside can be found in a number of food items such as redcurrant, gooseberry, highbush blueberry, and blackcurrant, which makes ferulic acid 4-glucoside a potential biomarker for the consumption of these food products.
Structure
Thumb
Synonyms
ValueSource
(2E)-3-(3-Methoxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoateGenerator
Ferulate 4-glucosideGenerator
(2E)-3-[4-(beta-D-Glucopyranosyloxy)-3-methoxyphenyl]-2-propenoic acidPhytoBank
(2E)-3-[4-(β-D-Glucopyranosyloxy)-3-methoxyphenyl]-2-propenoic acidPhytoBank
(E)-Ferulic acid 4-O-beta-D-glucosidePhytoBank
(E)-Ferulic acid 4-O-β-D-glucosidePhytoBank
Ferulic acid 4-O-glucosidePhytoBank
Ferulic acid 4-O-beta-glucopyranosidePhytoBank
Ferulic acid 4-O-β-glucopyranosidePhytoBank
LavandosidePhytoBank
trans-4-O-beta-D-Glucopyranosylferulic acidPhytoBank
trans-4-O-β-D-Glucopyranosylferulic acidPhytoBank
trans-Ferulic acid 4-beta-D-glucosidePhytoBank
trans-Ferulic acid 4-β-D-glucosidePhytoBank
trans-Ferulic acid-4-beta-glucosidePhytoBank
trans-Ferulic acid-4-β-glucosidePhytoBank
trans-p-Feruloyl-beta-D-glucopyranosidePhytoBank
trans-p-Feruloyl-β-D-glucopyranosidePhytoBank
Ferulic acid 4-O-beta-D-glucopyranosidePhytoBank
Ferulic acid 4-O-β-D-glucopyranosidePhytoBank
Chemical FormulaC16H20O9
Average Molecular Weight356.3246
Monoisotopic Molecular Weight356.110732238
IUPAC Name(2E)-3-(3-methoxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoic acid
Traditional Name(2E)-3-(3-methoxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoic acid
CAS Registry Number537-98-4
SMILES
COC1=CC(\C=C\C(O)=O)=CC=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O
InChI Identifier
InChI=1S/C16H20O9/c1-23-10-6-8(3-5-12(18)19)2-4-9(10)24-16-15(22)14(21)13(20)11(7-17)25-16/h2-6,11,13-17,20-22H,7H2,1H3,(H,18,19)/b5-3+/t11-,13-,14+,15-,16-/m1/s1
InChI KeyIEMIRSXOYFWPFD-BJGSYIFTSA-N
Chemical Taxonomy
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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentPhenolic glycosides
Alternative Parents
Substituents
  • Phenolic glycoside
  • Cinnamic acid
  • Cinnamic acid or derivatives
  • Coumaric acid or derivatives
  • Hexose monosaccharide
  • O-glycosyl compound
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Styrene
  • Phenol ether
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Benzenoid
  • Monosaccharide
  • Oxane
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Ether
  • Organoheterocyclic compound
  • Oxacycle
  • Carboxylic acid
  • Carboxylic acid derivative
  • Acetal
  • Polyol
  • Alcohol
  • Carbonyl group
  • Organic oxide
  • Primary alcohol
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP-0.29ALOGPS
logP-0.59ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)3.57ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area145.91 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity83.65 m³·mol⁻¹ChemAxon
Polarizability34.8 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M+H]+183.33132859911
AllCCS[M+H-H2O]+180.46332859911
AllCCS[M+Na]+186.73632859911
AllCCS[M+NH4]+185.97832859911
AllCCS[M-H]-179.62632859911
AllCCS[M+Na-2H]-179.8132859911
AllCCS[M+HCOO]-180.14832859911
DeepCCS[M+H]+180.15130932474
DeepCCS[M-H]-177.75630932474
DeepCCS[M-2H]-211.47330932474
DeepCCS[M+Na]+186.45830932474

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ferulic acid 4-glucoside 10V, Positive-QTOFsplash10-054t-0916000000-ebc1cc4896fdc64a458c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ferulic acid 4-glucoside 20V, Positive-QTOFsplash10-002b-0900000000-6a902dabbbf78442f23e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ferulic acid 4-glucoside 40V, Positive-QTOFsplash10-004s-1900000000-e4ad1acd6f4850f0bc2e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ferulic acid 4-glucoside 10V, Negative-QTOFsplash10-0a4l-1819000000-eba6f8f85bf8d5d539342016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ferulic acid 4-glucoside 20V, Negative-QTOFsplash10-002f-1911000000-77f2053078c1eb574d282016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ferulic acid 4-glucoside 40V, Negative-QTOFsplash10-004l-2900000000-2ff1d99e129350f506212016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ferulic acid 4-glucoside 10V, Positive-QTOFsplash10-052s-0219000000-b7234cdb53b60902464c2021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ferulic acid 4-glucoside 20V, Positive-QTOFsplash10-01y2-0914000000-a18d425b2a03a2eee99b2021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ferulic acid 4-glucoside 40V, Positive-QTOFsplash10-001j-1920000000-3cd8ce35afe706d70b232021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ferulic acid 4-glucoside 10V, Negative-QTOFsplash10-0a4i-0109000000-be106f09d2f43d279f4f2021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ferulic acid 4-glucoside 20V, Negative-QTOFsplash10-0002-2893000000-9a4389f84bbaed5643152021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ferulic acid 4-glucoside 40V, Negative-QTOFsplash10-0002-3902000000-98c283edf136c4ee19bf2021-10-21Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB000256
KNApSAcK IDNot Available
Chemspider ID10212167
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available