Showing metabocard for 4-Hydroxyphenyl-beta-glucopyranoside (BMDB0062094)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2018-06-25 21:50:15 UTC
Update Date2020-03-13 17:33:35 UTC
BMDB IDBMDB0062094
Secondary Accession Numbers
  • BMDB62094
Metabolite Identification
Common Name4-Hydroxyphenyl-beta-glucopyranoside
DescriptionArbutin, also known as ursin or uvasol, 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. Arbutin exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
Hydroquinone-O-beta-D-glucopyranosideChEBI
p-Hydroxyphenyl beta-D-glucopyranosideChEBI
p-Hydroxyphenyl beta-D-glucosideChEBI
UrsinChEBI
UvasolChEBI
Hydroquinone-O-b-D-glucopyranosideGenerator
Hydroquinone-O-β-D-glucopyranosideGenerator
p-Hydroxyphenyl b-D-glucopyranosideGenerator
p-Hydroxyphenyl β-D-glucopyranosideGenerator
p-Hydroxyphenyl b-D-glucosideGenerator
p-Hydroxyphenyl β-D-glucosideGenerator
4-Hydroxyphenyl-b-glucopyranosideHMDB
4-Hydroxyphenyl-β-glucopyranosideHMDB
4-Hydroxyphenyl beta-D-glucopyranosideHMDB
4-Hydroxyphenyl β-D-glucopyranosideHMDB
ArbutineHMDB
ArbutosideHMDB
ArbutyneHMDB
Hydroquinone beta-D-glucopyranosideHMDB
Hydroquinone glucoseHMDB
Hydroquinone β-D-glucopyranosideHMDB
beta-ArbutinHMDB
p-ArbutinHMDB
Β-arbutinHMDB
ArbutinChEBI
Chemical FormulaC12H16O7
Average Molecular Weight272.2512
Monoisotopic Molecular Weight272.089602866
IUPAC Name(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(4-hydroxyphenoxy)oxane-3,4,5-triol
Traditional Nameβ-arbutin
CAS Registry Number497-76-7
SMILES
[H][C@]1(CO)O[C@@]([H])(OC2=CC=C(O)C=C2)[C@]([H])(O)[C@@]([H])(O)[C@]1([H])O
InChI Identifier
InChI=1S/C12H16O7/c13-5-8-9(15)10(16)11(17)12(19-8)18-7-3-1-6(14)2-4-7/h1-4,8-17H,5H2/t8-,9-,10+,11-,12-/m1/s1
InChI KeyBJRNKVDFDLYUGJ-RMPHRYRLSA-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
  • 4-alkoxyphenol
  • Phenoxy compound
  • Phenol ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Monosaccharide
  • Benzenoid
  • Oxane
  • Secondary alcohol
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Alcohol
  • Primary alcohol
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-1.4ALOGPS
logP-0.9ChemAxon
logS-0.84ALOGPS
pKa (Strongest Acidic)9.82ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area119.61 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity62.16 m³·mol⁻¹ChemAxon
Polarizability25.88 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (5 TMS)splash10-0uxr-1971000000-e8260464bad4d4a7fa0cView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0uxs-0940000000-9984522469f86670798fView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0r00-9750000000-b52a5d3b5fb7e98f0009View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-0002-0090000000-a7028a3a9618849334b7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0229-0920000000-532b692f9942a62cc7c8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0229-0910000000-1cb0580496288b7004fcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-001i-0950000000-4bafd0325d0163331c0aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-001i-0950000000-ffffdfe1cd448f0ea135View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-016r-0290000000-0ebc801fded534434aa5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-016r-0390000000-5831b5a141106482d24dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 75V, Negativesplash10-0a4i-0900000000-e517344bdabb66a133e9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 60V, Negativesplash10-0a4i-0900000000-315daa57d6f694ca71fbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0a4i-1900000000-df811a65eba1be7fd68dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 45V, Negativesplash10-0a4i-0900000000-4efe3ed1e7614387deb4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 90V, Positivesplash10-014i-9000000000-6f8b05f1e0b20e00a25fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-014i-9100000000-7092290163d035871936View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0a4i-0900000000-a0b2ea306ed135900292View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 15V, Negativesplash10-0a4i-1900000000-26385cb99dd5b38d4f3cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 90V, Negativesplash10-0a4i-0900000000-0a4c12f1e9730c4685eaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03k9-0970000000-e87519bd2c30ca193e5eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-1900000000-f812a22889a4e7871758View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03e9-9600000000-9a8f2b8fb568a07413b4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05fr-1890000000-cb67c77a9f0c57c986bdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-1910000000-52b74ad8f6f3181df26dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-5900000000-45bf1851196d0254c239View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ab9-0950000000-597b2277ebb9d13fbb41View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ab9-4940000000-6a46c2768079c1935cb9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-7900000000-56f28af9a02294ffb2faView in MoNA
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Milk
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
HMDB IDHMDB0029943
DrugBank IDDB11217
Phenol Explorer Compound IDNot Available
FooDB IDFDB030911
KNApSAcK IDC00002638
Chemspider ID389765
KEGG Compound IDC06186
BioCyc IDHYDROQUINONE-O-BETA-D-GLUCOPYRANOSIDE
BiGG IDNot Available
Wikipedia LinkArbutin
METLIN IDNot Available
PubChem Compound440936
PDB IDNot Available
ChEBI ID18305
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. [PubMed:23438684 ]