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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-24 04:56:04 UTC
Update Date2022-09-22 18:35:14 UTC
HMDB IDHMDB0303826
Secondary Accession NumbersNone
Metabolite Identification
Common NameProtocatechuic acid 4-glucoside
DescriptionProtocatechuic 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. Protocatechuic acid 4-glucoside is soluble (in water) and a weakly acidic compound (based on its pKa). Protocatechuic acid 4-glucoside can be found in a number of food items such as rosemary, jostaberry, rubus (blackberry, raspberry), and highbush blueberry, which makes protocatechuic acid 4-glucoside a potential biomarker for the consumption of these food products.
Structure
Thumb
Synonyms
ValueSource
3-Hydroxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoateGenerator
Protocatechuate 4-glucosideGenerator
Chemical FormulaC13H16O9
Average Molecular Weight316.262
Monoisotopic Molecular Weight316.079432095
IUPAC Name3-hydroxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoic acid
Traditional Name3-hydroxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoic acid
CAS Registry NumberNot Available
SMILES
OCC1OC(OC2=C(O)C=C(C=C2)C(O)=O)C(O)C(O)C1O
InChI Identifier
InChI=1S/C13H16O9/c14-4-8-9(16)10(17)11(18)13(22-8)21-7-2-1-5(12(19)20)3-6(7)15/h1-3,8-11,13-18H,4H2,(H,19,20)
InChI KeyHFFREILXLCWCQH-UHFFFAOYSA-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
  • Hexose monosaccharide
  • O-glycosyl compound
  • Hydroxybenzoic acid
  • Benzoic acid or derivatives
  • Benzoic acid
  • Phenoxy compound
  • Phenol ether
  • Benzoyl
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Sugar acid
  • Oxane
  • Monocyclic benzene moiety
  • Benzenoid
  • Monosaccharide
  • 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 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-0.94ALOGPS
logP-1.2ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)4.1ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area156.91 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity69.42 m³·mol⁻¹ChemAxon
Polarizability29.23 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M+H]+172.04632859911
AllCCS[M+H-H2O]+168.85232859911
AllCCS[M+Na]+175.8532859911
AllCCS[M+NH4]+175.00232859911
AllCCS[M-H]-168.08532859911
AllCCS[M+Na-2H]-167.9532859911
AllCCS[M+HCOO]-167.92532859911
DeepCCS[M+H]+167.0530932474
DeepCCS[M-H]-164.69230932474
DeepCCS[M-2H]-198.24830932474
DeepCCS[M+Na]+173.47530932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Protocatechuic acid 4-glucoside,3TBDMS,isomer #5CC(C)(C)[Si](C)(C)OCC1OC(OC2=CC=C(C(=O)O)C=C2O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C1O3540.8Semi standard non polar33892256
Protocatechuic acid 4-glucoside,3TBDMS,isomer #5CC(C)(C)[Si](C)(C)OCC1OC(OC2=CC=C(C(=O)O)C=C2O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C1O3519.3Standard non polar33892256
Protocatechuic acid 4-glucoside,3TBDMS,isomer #5CC(C)(C)[Si](C)(C)OCC1OC(OC2=CC=C(C(=O)O)C=C2O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C1O3879.9Standard polar33892256
Protocatechuic acid 4-glucoside,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC1OC(OC2=CC=C(C(=O)O[Si](C)(C)C(C)(C)C)C=C2O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C1O3669.3Semi standard non polar33892256
Protocatechuic acid 4-glucoside,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC1OC(OC2=CC=C(C(=O)O[Si](C)(C)C(C)(C)C)C=C2O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C1O3665.4Standard non polar33892256
Protocatechuic acid 4-glucoside,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC1OC(OC2=CC=C(C(=O)O[Si](C)(C)C(C)(C)C)C=C2O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C1O3721.2Standard polar33892256
Protocatechuic acid 4-glucoside,4TBDMS,isomer #7CC(C)(C)[Si](C)(C)OCC1OC(OC2=CC=C(C(=O)O)C=C2O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1O3718.6Semi standard non polar33892256
Protocatechuic acid 4-glucoside,4TBDMS,isomer #7CC(C)(C)[Si](C)(C)OCC1OC(OC2=CC=C(C(=O)O)C=C2O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1O3591.9Standard non polar33892256
Protocatechuic acid 4-glucoside,4TBDMS,isomer #7CC(C)(C)[Si](C)(C)OCC1OC(OC2=CC=C(C(=O)O)C=C2O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1O3665.1Standard polar33892256
Protocatechuic acid 4-glucoside,4TBDMS,isomer #8CC(C)(C)[Si](C)(C)OCC1OC(OC2=CC=C(C(=O)O)C=C2O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C1O[Si](C)(C)C(C)(C)C3740.7Semi standard non polar33892256
Protocatechuic acid 4-glucoside,4TBDMS,isomer #8CC(C)(C)[Si](C)(C)OCC1OC(OC2=CC=C(C(=O)O)C=C2O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C1O[Si](C)(C)C(C)(C)C3648.6Standard non polar33892256
Protocatechuic acid 4-glucoside,4TBDMS,isomer #8CC(C)(C)[Si](C)(C)OCC1OC(OC2=CC=C(C(=O)O)C=C2O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C1O[Si](C)(C)C(C)(C)C3685.9Standard polar33892256
Protocatechuic acid 4-glucoside,5TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC1OC(OC2=CC=C(C(=O)O[Si](C)(C)C(C)(C)C)C=C2O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1O3868.8Semi standard non polar33892256
Protocatechuic acid 4-glucoside,5TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC1OC(OC2=CC=C(C(=O)O[Si](C)(C)C(C)(C)C)C=C2O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1O3710.2Standard non polar33892256
Protocatechuic acid 4-glucoside,5TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC1OC(OC2=CC=C(C(=O)O[Si](C)(C)C(C)(C)C)C=C2O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1O3568.1Standard polar33892256
Protocatechuic acid 4-glucoside,5TBDMS,isomer #2CC(C)(C)[Si](C)(C)OCC1OC(OC2=CC=C(C(=O)O[Si](C)(C)C(C)(C)C)C=C2O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C1O[Si](C)(C)C(C)(C)C3899.3Semi standard non polar33892256
Protocatechuic acid 4-glucoside,5TBDMS,isomer #2CC(C)(C)[Si](C)(C)OCC1OC(OC2=CC=C(C(=O)O[Si](C)(C)C(C)(C)C)C=C2O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C1O[Si](C)(C)C(C)(C)C3763.1Standard non polar33892256
Protocatechuic acid 4-glucoside,5TBDMS,isomer #2CC(C)(C)[Si](C)(C)OCC1OC(OC2=CC=C(C(=O)O[Si](C)(C)C(C)(C)C)C=C2O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C1O[Si](C)(C)C(C)(C)C3580.7Standard polar33892256
Protocatechuic acid 4-glucoside,5TBDMS,isomer #5CC(C)(C)[Si](C)(C)OCC1OC(OC2=CC=C(C(=O)O)C=C2O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1O[Si](C)(C)C(C)(C)C3902.3Semi standard non polar33892256
Protocatechuic acid 4-glucoside,5TBDMS,isomer #5CC(C)(C)[Si](C)(C)OCC1OC(OC2=CC=C(C(=O)O)C=C2O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1O[Si](C)(C)C(C)(C)C3681.4Standard non polar33892256
Protocatechuic acid 4-glucoside,5TBDMS,isomer #5CC(C)(C)[Si](C)(C)OCC1OC(OC2=CC=C(C(=O)O)C=C2O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1O[Si](C)(C)C(C)(C)C3478.8Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Protocatechuic acid 4-glucoside GC-MS (Non-derivatized) - 70eV, Positivesplash10-0pbj-9570000000-6d30d9f6adf5b185e7ca2017-07-27Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Protocatechuic acid 4-glucoside 10V, Positive-QTOFsplash10-0aos-0953000000-00458630ff20f9da94522017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Protocatechuic acid 4-glucoside 20V, Positive-QTOFsplash10-0a4i-0910000000-cdc0cc0b11c3f192f3ed2017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Protocatechuic acid 4-glucoside 40V, Positive-QTOFsplash10-0a4r-2900000000-5e95efbc21405759814a2017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Protocatechuic acid 4-glucoside 10V, Negative-QTOFsplash10-0gb9-1957000000-391572d3667b5707b2322017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Protocatechuic acid 4-glucoside 20V, Negative-QTOFsplash10-0zfr-1920000000-de37ab8c3b253a4e36082017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Protocatechuic acid 4-glucoside 40V, Negative-QTOFsplash10-0pb9-3900000000-de8c096d899726f8d0652017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Protocatechuic acid 4-glucoside 10V, Positive-QTOFsplash10-0002-0954000000-b26c42eeb3c97745fb782021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Protocatechuic acid 4-glucoside 20V, Positive-QTOFsplash10-052k-1930000000-0cf9dde76564d38383d52021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Protocatechuic acid 4-glucoside 40V, Positive-QTOFsplash10-05fs-9800000000-5e9a94e36f969ad6926f2021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Protocatechuic acid 4-glucoside 10V, Negative-QTOFsplash10-0uxr-0935000000-f65e714c5693f8b014b12021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Protocatechuic acid 4-glucoside 20V, Negative-QTOFsplash10-0zfr-3931000000-2f38d5a75a6cdabe93bb2021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Protocatechuic acid 4-glucoside 40V, Negative-QTOFsplash10-052f-9500000000-4ee641510c5250432df32021-10-21Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedAdult (>18 years old)BothAsthma details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothAsthma details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB021851
KNApSAcK IDNot Available
Chemspider IDNot Available
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