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Showing metabocard for Arbutin (HMDB0029943)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:33:42 UTC
Update Date2020-09-28 03:30:24 UTC
HMDB IDHMDB0029943
Secondary Accession Numbers
  • HMDB29943
Metabolite Identification
Common NameArbutin
DescriptionArbutin is found in apple. Glucoside in pear leaves (Pyrus communis
Structure
Data?1601263824
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
ArbutinChEBI
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-glucopyranosideGenerator
4-Hydroxyphenyl-β-glucopyranosideGenerator
4-Hydroxyphenyl beta-D-glucopyranosidePhytoBank
4-Hydroxyphenyl β-D-glucopyranosidePhytoBank
ArbutinePhytoBank
ArbutosidePhytoBank
ArbutynePhytoBank
Hydroquinone beta-D-glucopyranosidePhytoBank
Hydroquinone glucosePhytoBank
Hydroquinone β-D-glucopyranosidePhytoBank
beta-ArbutinPhytoBank
p-ArbutinPhytoBank
β-ArbutinPhytoBank
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
OC[C@H]1O[C@@H](OC2=CC=C(O)C=C2)[C@H](O)[C@@H](O)[C@@H]1O
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
Disposition

Route of exposure:

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point142 - 143 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-1.35Not Available
Predicted Properties
PropertyValueSource
Water Solubility39.1 g/LALOGPS
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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (5 TMS)splash10-0uxr-1971000000-e8260464bad4d4a7fa0cSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0uxs-0940000000-9984522469f86670798fSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0r00-9750000000-b52a5d3b5fb7e98f0009Spectrum
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-0002-0090000000-a7028a3a9618849334b7Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0229-0920000000-532b692f9942a62cc7c8Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0229-0910000000-1cb0580496288b7004fcSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-001i-0950000000-4bafd0325d0163331c0aSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-001i-0950000000-ffffdfe1cd448f0ea135Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-016r-0290000000-0ebc801fded534434aa5Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-016r-0390000000-5831b5a141106482d24dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03k9-0970000000-e87519bd2c30ca193e5eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-1900000000-f812a22889a4e7871758Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03e9-9600000000-9a8f2b8fb568a07413b4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05fr-1890000000-cb67c77a9f0c57c986bdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-1910000000-52b74ad8f6f3181df26dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-5900000000-45bf1851196d0254c239Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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 IDDB11217
Phenol Explorer Compound IDNot Available
FooDB IDFDB030911
KNApSAcK IDC00002638
Chemspider IDNot Available
KEGG Compound IDC06186
BioCyc IDHYDROQUINONE-O-BETA-D-GLUCOPYRANOSIDE
BiGG IDNot Available
Wikipedia LinkArbutin
METLIN IDNot Available
PubChem Compound440936
PDB IDNot Available
ChEBI ID18305
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Siegers C, Bodinet C, Ali SS, Siegers CP: Bacterial deconjugation of arbutin by Escherichia coli. Phytomedicine. 2003;10 Suppl 4:58-60. [PubMed:12807345 ]
  2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .