Record Information
Creation date2010-04-08 22:04:26 UTC
Update date2019-11-26 02:54:31 UTC
Primary IDFDB000084
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePhloretin-2'-O-(2''-O-xylosylglucoside)
DescriptionPhloretin-2'-o-(2''-o-xylosylglucoside) is a member of the class of compounds known as flavonoid o-glycosides. Flavonoid o-glycosides are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone. Phloretin-2'-o-(2''-o-xylosylglucoside) is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Phloretin-2'-o-(2''-o-xylosylglucoside) can be found in apple, apricot, and pear, which makes phloretin-2'-o-(2''-o-xylosylglucoside) a potential biomarker for the consumption of these food products.
CAS Number60-82-2
Phloretin 2'-O-xylosyl-glucosidemanual
Predicted Properties
Water Solubility2.78 g/LALOGPS
pKa (Strongest Acidic)7.87ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area236.06 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity132.3 m³·mol⁻¹ChemAxon
Polarizability55.1 ųChemAxon
Number of Rings4ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC26H32O14
IUPAC name1-(2-{[(2S,3R,4S,5S,6R)-3-{[(2S,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,6-dihydroxyphenyl)-3-(4-hydroxyphenyl)propan-1-one
InChI IdentifierInChI=1S/C26H32O14/c27-9-17-20(33)22(35)24(40-25-23(36)21(34)18(10-28)38-25)26(39-17)37-16-8-13(30)7-15(32)19(16)14(31)6-3-11-1-4-12(29)5-2-11/h1-2,4-5,7-8,17-18,20-30,32-36H,3,6,9-10H2/t17-,18-,20-,21+,22+,23-,24-,25+,26-/m1/s1
Isomeric SMILESOC[C@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]2OC2=C(C(=O)CCC3=CC=C(O)C=C3)C(O)=CC(O)=C2)[C@H](O)[C@H]1O
Average Molecular Weight568.5239
Monoisotopic Molecular Weight568.179205732
Description Belongs to the class of organic compounds known as flavonoid o-glycosides. Flavonoid O-glycosides are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid O-glycosides
Alternative Parents
  • Flavonoid o-glycoside
  • 2'-hydroxy-dihydrochalcone
  • Linear 1,3-diarylpropanoid
  • Cinnamylphenol
  • Phenolic glycoside
  • Alkyl-phenylketone
  • O-glycosyl compound
  • Glycosyl compound
  • Butyrophenone
  • Disaccharide
  • Phenylketone
  • Phenol ether
  • Phenoxy compound
  • Resorcinol
  • Benzoyl
  • Aryl ketone
  • Aryl alkyl ketone
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • 1-hydroxy-4-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Oxane
  • Benzenoid
  • Tetrahydrofuran
  • Vinylogous acid
  • Secondary alcohol
  • Ketone
  • Acetal
  • Organoheterocyclic compound
  • Oxacycle
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Primary alcohol
  • Organooxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting Point263.5 oC
Boiling PointNot Available
Experimental Water Solubility0.123 mg/mL at 16 oCBEILSTEIN
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
EI-MS/GC-MSNot Available
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00or-0290640000-ebacf57060d275359e13Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-0691300000-7871bf67fe36442d9c7eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05r0-1971100000-cafa12df75de1bed9198Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01b9-2382980000-0e9b59f7d9cf9ac1de0eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00ea-0970310000-c9c818ed6fba24744dfbSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-3960000000-a8d5ea47784510b18293Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gbi-0630690000-2fc95214d77c627e6c53Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pb9-1900130000-c8b6498a96977432b9a3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ab9-9200110000-080b8a1e62b097b73d39Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000290000-226fd0858b077b414116Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-2000900000-b5f86dd5205fde29b222Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9410400000-dd716f047d81e7378c55Spectrum
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 ID111
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
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
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
MSDSNot Available
Synthesis ReferenceNot Available
General Reference
  1. Marks SC, Mullen W, Borges G, Crozier A: Absorption, metabolism, and excretion of cider dihydrochalcones in healthy humans and subjects with an ileostomy. J Agric Food Chem. 2009 Mar 11;57(5):2009-15. Pubmed [Structure]
Content Reference— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.