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Showing Compound Phloretin-2'-O-(2''-O-xylosylglucoside) (FDB000084)

Record Information
Version1.0
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
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Phloretin 2'-O-xylosyl-glucosidemanual
Predicted Properties
PropertyValueSource
Water Solubility2.78 g/LALOGPS
logP-0.29ALOGPS
logP-0.16ChemAxon
logS-2.3ALOGPS
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
BioavailabilityNoChemAxon
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
InChI KeyZPVXZDCYCDBKAJ-NCMRLHFPSA-N
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
Classification
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
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid O-glycosides
Alternative Parents
Substituents
  • 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
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
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
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00or-0290640000-ebacf57060d275359e132016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-0691300000-7871bf67fe36442d9c7e2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05r0-1971100000-cafa12df75de1bed91982016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01b9-2382980000-0e9b59f7d9cf9ac1de0e2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00ea-0970310000-c9c818ed6fba24744dfb2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-3960000000-a8d5ea47784510b182932016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gbi-0630690000-2fc95214d77c627e6c532021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pb9-1900130000-c8b6498a96977432b9a32021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ab9-9200110000-080b8a1e62b097b73d392021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000290000-226fd0858b077b4141162021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-2000900000-b5f86dd5205fde29b2222021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9410400000-dd716f047d81e7378c552021-10-21View Spectrum
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
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 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.