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Record Information
Version3.6
Creation Date2007-01-23 13:47:12 UTC
Update Date2016-02-11 01:07:17 UTC
HMDB IDHMDB05810
Secondary Accession NumbersNone
Metabolite Identification
Common NameEriodictyol
DescriptionEriodictyol is a flavonoid, a compound isolated from Eriodictyon californicum and can be used in medicine as an expectorant.
Structure
Thumb
Synonyms
ValueSource
(S)-2-(3,4-Dihydroxyphenyl)-2,3-dihydro-5,7-dihydroxy-4-benzopyroneChEBI
EriodictiolChEBI
Chemical FormulaC15H12O6
Average Molecular Weight288.2522
Monoisotopic Molecular Weight288.063388116
IUPAC Name(2S)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-4-one
Traditional Nameeriodictyol
CAS Registry Number552-58-9
SMILES
OC1=CC2=C(C(=O)C[C@H](O2)C2=CC(O)=C(O)C=C2)C(O)=C1
InChI Identifier
InChI=1S/C15H12O6/c16-8-4-11(19)15-12(20)6-13(21-14(15)5-8)7-1-2-9(17)10(18)3-7/h1-5,13,16-19H,6H2/t13-/m0/s1
InChI KeyInChIKey=SBHXYTNGIZCORC-ZDUSSCGKSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as flavanones. These are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a ketone at the carbon C3.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavans
Direct ParentFlavanones
Alternative Parents
Substituents
  • Hydroxyflavonoid
  • Flavanone
  • 7-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 3'-hydroxyflavonoid
  • Chromone
  • 1-benzopyran
  • Benzopyran
  • Chromane
  • Aryl alkyl ketone
  • Aryl ketone
  • Resorcinol
  • 1,2-diphenol
  • Phenol
  • Alkyl aryl ether
  • Benzenoid
  • Monocyclic benzene moiety
  • Vinylogous acid
  • Ketone
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Drug
  • Drug metabolite
  • Plant
Biofunction
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Membrane (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point269 - 270 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.07 mg/mL at 20 °CNot Available
LogP2.02PERRISSOUD,D & TESTA,B (1986)
Predicted Properties
PropertyValueSource
Water Solubility0.37 mg/mLALOGPS
logP2.15ALOGPS
logP2.53ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)7.9ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area107.22 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity73.27 m3·mol-1ChemAxon
Polarizability27.32 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNot Available
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDDBMET00253
Phenol Explorer Compound ID202
Phenol Explorer Metabolite ID202
FoodDB IDFDB000688
KNApSAcK IDC00000960
Chemspider ID389606
KEGG Compound IDC05631
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEriodictyol
NuGOwiki LinkHMDB05810
Metagene LinkHMDB05810
METLIN ID3415
PubChem Compound440735
PDB IDERD
ChEBI ID28412
References
Synthesis ReferencePowers, Fred B.; Tutin, Frank. Chemical Examination of Eriodictyon. Pharmaceutical Review (1907), 24 301.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 'T Hart BA, Ip Via Ching TR, Van Dijk H, Labadie RP: How flavonoids inhibit the generation of luminol-dependent chemiluminescence by activated human neutrophils. Chem Biol Interact. 1990;73(2-3):323-35. [2155715 ]
  2. Miyake Y, Sakurai C, Usuda M, Fukumoto S, Hiramitsu M, Sakaida K, Osawa T, Kondo K: Difference in plasma metabolite concentration after ingestion of lemon flavonoids and their aglycones in humans. J Nutr Sci Vitaminol (Tokyo). 2006 Feb;52(1):54-60. [16637230 ]
  3. Ogata S, Miyake Y, Yamamoto K, Okumura K, Taguchi H: Apoptosis induced by the flavonoid from lemon fruit (Citrus limon BURM. f.) and its metabolites in HL-60 cells. Biosci Biotechnol Biochem. 2000 May;64(5):1075-8. [10879486 ]