5-(3',5'-Dihydroxyphenyl)-gamma-valerolactone 3-glucuronide (CHEM041562)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-27 01:34:18 UTC
Update Date2016-11-09 01:22:30 UTC
Accession NumberCHEM041562
Identification
Common Name5-(3',5'-Dihydroxyphenyl)-gamma-valerolactone 3-glucuronide
ClassSmall Molecule
Description5-(3',5'-Dihydroxyphenyl)-gamma-valerolactone 3-O-glucuronide is a polyphenol metabolite detected in biological fluids (PMID: 20428313).
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
5-(3',5'-Dihydroxyphenyl)-g-valerolactone 3-O-glucuronideGenerator
5-(3',5'-Dihydroxyphenyl)-γ-valerolactone 3-O-glucuronideGenerator
(2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-{3-hydroxy-5-[(5-oxooxolan-2-yl)methyl]phenoxy}oxane-2-carboxylateHMDB
5-(3',5'-Dihydroxyphenyl)-g-valerolactone 3-glucuronideHMDB
5-(3',5'-Dihydroxyphenyl)-γ-valerolactone 3-glucuronideHMDB
Chemical FormulaC17H20O10
Average Molecular Mass384.335 g/mol
Monoisotopic Mass384.106 g/mol
CAS Registry NumberNot Available
IUPAC Name(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{3-hydroxy-5-[(5-oxooxolan-2-yl)methyl]phenoxy}oxane-2-carboxylic acid
Traditional Name(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{3-hydroxy-5-[(5-oxooxolan-2-yl)methyl]phenoxy}oxane-2-carboxylic acid
SMILESO[C@@H]1[C@@H](O)[C@H](OC2=CC(O)=CC(CC3CCC(=O)O3)=C2)O[C@@H]([C@H]1O)C(O)=O
InChI IdentifierInChI=1S/C17H20O10/c18-8-3-7(4-9-1-2-11(19)25-9)5-10(6-8)26-17-14(22)12(20)13(21)15(27-17)16(23)24/h3,5-6,9,12-15,17-18,20-22H,1-2,4H2,(H,23,24)/t9?,12-,13-,14+,15-,17+/m0/s1
InChI KeyRUSMDDXSDLDLKU-PHPHFFAHSA-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
  • 1-o-glucuronide
  • O-glucuronide
  • Glucuronic acid or derivatives
  • O-glycosyl compound
  • Phenoxy compound
  • Phenol ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Beta-hydroxy acid
  • Phenol
  • Monocyclic benzene moiety
  • Dicarboxylic acid or derivatives
  • Gamma butyrolactone
  • Hydroxy acid
  • Monosaccharide
  • Benzenoid
  • Oxane
  • Pyran
  • Tetrahydrofuran
  • Lactone
  • Secondary alcohol
  • Carboxylic acid ester
  • Acetal
  • Carboxylic acid
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Polyol
  • Organic oxide
  • Hydrocarbon derivative
  • Alcohol
  • Carbonyl group
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
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 Solubility6.91 g/LALOGPS
logP-0.26ALOGPS
logP-0.33ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)3.14ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area162.98 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity85.32 m³·mol⁻¹ChemAxon
Polarizability35.89 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-07vs-7393000000-9e5d2516c1bfcf90a3a4Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-0a4i-3022029000-4fb28db4992e513764acSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ap0-0449000000-5139e0a7c2df22349522Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4s-0931000000-a4004bfe97b134711408Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-059e-1910000000-7c6816701e1c3ff504d6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0540-1339000000-318726d27da0c33c62a1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-3795000000-1307b07d619b8baedc2aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0btc-8930000000-931db6da95b7bf8a978aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05o0-0239000000-7c65704b4b9e8f33f4b7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-6793000000-3e14f71356901c28cab5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-2910000000-f49273419e127ee75359Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-0249000000-62eab577644c14d2d54aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0699-0549000000-5b06ea36602ad433dfafSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ar0-2931000000-c85dd8dcf56ecae9b078Spectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
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 IDHMDB0041693
FooDB IDFDB029857
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID35015220
ChEBI ID88659
PubChem Compound ID124202085
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Neveu V, Perez-Jimenez J, Vos F, Crespy V, du Chaffaut L, Mennen L, Knox C, Eisner R, Cruz J, Wishart D, Scalbert A: Phenol-Explorer: an online comprehensive database on polyphenol contents in foods. Database (Oxford). 2010;2010:bap024. doi: 10.1093/database/bap024. Epub 2010 Jan 8.