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Showing Compound 2,4,6-Phenanthrenetriol 2-O-b-D-glucoside (FDB015206)

Record Information
Version1.0
Creation date2010-04-08 22:11:42 UTC
Update date2019-11-26 03:11:17 UTC
Primary IDFDB015206
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name2,4,6-Phenanthrenetriol 2-O-b-D-glucoside
Description2,4,6-Phenanthrenetriol 2-O-b-D-glucoside 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. 2,4,6-Phenanthrenetriol 2-O-b-D-glucoside is an extremely weak basic (essentially neutral) compound (based on its pKa). 2,4,6-Phenanthrenetriol 2-O-b-D-glucoside has been detected, but not quantified in, alcoholic beverages. This could make 2,4,6-phenanthrenetriol 2-O-b-D-glucoside a potential biomarker for the consumption of these foods.
CAS Number95-01-2
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
2,4,6-Phenanthrenetriol 2-O-b-D-glucopyranosidemanual
2,4,6-Phenanthrenetriol 2-O-b-D-glucosidemanual
2,4,6-Trihydroxyphenanthrene 2-O-b-D-glucopyranosidemanual
2,4,6-Trihydroxyphenanthrene 2-O-b-D-glucosidemanual
Predicted Properties
PropertyValueSource
Water Solubility1.15 g/LALOGPS
logP0.7ALOGPS
logP0.77ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)8.79ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area139.84 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity97.05 m³·mol⁻¹ChemAxon
Polarizability38.89 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC20H20O8
IUPAC name2-[(4,6-dihydroxyphenanthren-2-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
InChI IdentifierInChI=1S/C20H20O8/c21-8-15-17(24)18(25)19(26)20(28-15)27-12-5-10-2-1-9-3-4-11(22)6-13(9)16(10)14(23)7-12/h1-7,15,17-26H,8H2
InChI KeyOLRKGPYAYTYJGF-UHFFFAOYSA-N
Isomeric SMILESOCC1OC(OC2=CC(O)=C3C(C=CC4=CC=C(O)C=C34)=C2)C(O)C(O)C1O
Average Molecular Weight388.372
Monoisotopic Molecular Weight388.115817604
Classification
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
  • Phenanthrol
  • Phenanthrene
  • Hexose monosaccharide
  • 2-naphthol
  • 1-naphthol
  • O-glycosyl compound
  • Naphthalene
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Benzenoid
  • Oxane
  • Monosaccharide
  • Secondary alcohol
  • Polyol
  • Organoheterocyclic compound
  • Oxacycle
  • Acetal
  • Primary alcohol
  • Hydrocarbon derivative
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 61.85%; H 5.19%; O 32.96%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS2,4,6-Phenanthrenetriol 2-O-b-D-glucoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0fmi-9848000000-f32c15c6ea45717330ecSpectrum
Predicted GC-MS2,4,6-Phenanthrenetriol 2-O-b-D-glucoside, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03di-2402019000-d798832ea18be18a75f8Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004r-0196000000-c7fc65cc270b483c3b54Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0090000000-74a06af5adf5699afb03Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-1190000000-9b1ee8b436749b667691Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002r-1169000000-015a05fe349b46a63b68Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-1191000000-ee6718305f94cb2d86d7Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-3290000000-903d861f2e5a2cfb5fa7Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB36335
CRC / DFC (Dictionary of Food Compounds) IDFRH55-S:JYQ77-I
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference