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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:47:48 UTC
Update Date2018-03-12 21:56:00 UTC
HMDB IDHMDB0036634
Secondary Accession Numbers
  • HMDB36634
Metabolite Identification
Common NamePhlorizin
DescriptionPhlorizin is found in apple. Phlorizin is isolated from apple leaves and bark.Phlorizin is a toxic glycoside made by some plants. It belongs to the group of flavonoids. It is a competitive inhibitor of renal glucose transport.
Structure
Thumb
Synonyms
ValueSource
FloridzinChEBI
Phloretin 2'-glucosideChEBI
PhlorhizinChEBI
PhloridzinChEBI
PhlorizosideChEBI
Phloretin-2'-beta-glucosideHMDB
Phloretin-2'-O-beta-glucosideHMDB
PhloridzinumHMDB
PhloridzosidHMDB
PhlorizineHMDB
PhlorrhizenHMDB
PhlorrhizinHMDB
Chemical FormulaC21H24O10
Average Molecular Weight436.4093
Monoisotopic Molecular Weight436.136946988
IUPAC Name1-(2,4-dihydroxy-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3-(4-hydroxyphenyl)propan-1-one
Traditional Namephlorizin
CAS Registry Number60-81-1
SMILES
OC[C@H]1O[C@@H](OC2=CC(O)=CC(O)=C2C(=O)CCC2=CC=C(O)C=C2)[C@H](O)[C@@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C21H24O10/c22-9-16-18(27)19(28)20(29)21(31-16)30-15-8-12(24)7-14(26)17(15)13(25)6-3-10-1-4-11(23)5-2-10/h1-2,4-5,7-8,16,18-24,26-29H,3,6,9H2/t16-,18-,19+,20-,21-/m1/s1
InChI KeyIOUVKUPGCMBWBT-QNDFHXLGSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as flavonoid o-glycosides. These 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
  • Chalcone or dihydrochalcone
  • Phenolic glycoside
  • Cinnamylphenol
  • 2'-hydroxy-dihydrochalcone
  • Linear 1,3-diarylpropanoid
  • O-glycosyl compound
  • Glycosyl compound
  • Butyrophenone
  • Acylphloroglucinol derivative
  • Phloroglucinol derivative
  • Benzenetriol
  • Acetophenone
  • Aryl alkyl ketone
  • Aryl ketone
  • Resorcinol
  • Phenol ether
  • Benzoyl
  • Phenol
  • Benzenoid
  • Oxane
  • Monosaccharide
  • Saccharide
  • Monocyclic benzene moiety
  • Vinylogous acid
  • Secondary alcohol
  • Polyol
  • Ketone
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Acetal
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point110.0 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1 mg/mL at 22 °CNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.21 g/LALOGPS
logP0.44ALOGPS
logP0.98ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)7.89ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area177.14 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity105.85 m³·mol⁻¹ChemAxon
Polarizability42.42 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0gb9-5913400000-47cf252550936db167d6View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-000i-4760119000-72f18a2449892aa53ec3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-00di-0090000000-76b60140aba03098ef8dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-00di-0090000000-26c8a10836d524559b7aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-0092000000-90a57e1f22eef000cfc2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-0192000000-569b92df53d5414d6b9cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00or-0593000000-dd46ab71f853e528f809View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014i-0029500000-83a7b6481f9411db0c2aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014l-0029400000-1e2ddb25131a89de2473View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014l-0029400000-9b87e9e9e7047311fe43View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014l-0129300000-85b4094b3a111acabac5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-014i-0019700000-17beed8e63a40dbe0fadView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-014i-0019700000-e6f57c85d791f73ddac4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-014i-0019800000-04f42cab2c73ebc8bfddView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-014i-0019700000-83eac943753547575e74View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0002-0193100000-60d4307e81921a884881View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0002-0193100000-4ef83973bcb1d290871bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0079-1361900000-f4ac825585d69e78246eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-1591100000-4099114d9b7e981d8ed0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00xu-4790000000-c222fbd317f639c6ecf7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00p0-0290600000-83064b80a026d781f15aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pdi-0980000000-825463dfd002813e90b3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pdi-1930000000-d13d22201525f5a889b7View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
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 IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB015554
KNApSAcK IDC00000990
Chemspider ID16498836
KEGG Compound IDC01604
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPhlorizin
METLIN IDNot Available
PubChem Compound6072
PDB IDNot Available
ChEBI ID8113
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .