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Record Information
Version4.0
Creation Date2007-01-23 13:47:12 UTC
Update Date2017-09-27 08:24:39 UTC
HMDB IDHMDB0005810
Secondary Accession Numbers
  • HMDB05810
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 KeySBHXYTNGIZCORC-ZDUSSCGKSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassPhenylpropanoids and polyketides
Sub ClassFlavonoids
Direct ParentFlavanones
Alternative Parents
Substituents
  • Flavanone
  • 3'-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Hydroxyflavonoid
  • Chromone
  • Benzopyran
  • Chromane
  • 1-benzopyran
  • Catechol
  • Aryl ketone
  • Aryl alkyl ketone
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • 1-hydroxy-4-unsubstituted benzenoid
  • Alkyl aryl ether
  • Benzenoid
  • Monocyclic benzene moiety
  • Vinylogous acid
  • Ketone
  • Organoheterocyclic compound
  • Oxacycle
  • Ether
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

Source:

  Biological:

    Plant:

Role

Industrial application:

Biological role:

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 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity73.27 m³·mol⁻¹ChemAxon
Polarizability27.32 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, Positivesplash10-06y9-0690000000-250ba7bd6576410f8734View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-0imi-2530190000-6bcd43fd8b42301ed166View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-000i-0090000000-778b9cb4a7b875c6bbecView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-052r-0090000000-9178a74a6239d2ef3882View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-052r-0290000000-287f5fa660d816283c29View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0019-0090000000-cb3df3f82944d76bf224View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0019-0090000000-cb3df3f82944d76bf224View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-0019-0090000000-cb3df3f82944d76bf224View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-000i-0090000000-778b9cb4a7b875c6bbecView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-052r-0090000000-9178a74a6239d2ef3882View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-052r-0290000000-287f5fa660d816283c29View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0019-0090000000-cb3df3f82944d76bf224View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-000i-0090000000-772ca2fc672ef9668bfaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-000i-0920000000-4bc67dc66facd1fa75e5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0f79-0910000000-c48ad5f3958e9c41f5deView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-000i-0970000000-cb17dd84eda67cc9d6a4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-000i-0900000000-5c65882b59856d787f67View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0910000000-85200d3bfe0ef9f8c6cfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0f79-0900000000-8aa62dd381d8e70390e1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-1900000000-c83d3fbbf98b1c8e768dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0f79-0950000000-70ad9d5c48c3fd3ab1feView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0390000000-0dc39ca84a3e57cc4553View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0980000000-1ccfe66899ea0c7d03a3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fa9-4900000000-df7958810e2c56540877View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0190000000-a7838f78d4cef436da5fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0390000000-adb9e4c67817a09b2fd0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0apr-5940000000-9fb4bafc0204f514e65fView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineDetected and Quantified0.000694 umol/mmol creatinineAdult (>18 years old)BothNormal details
    UrineDetected and Quantified0.000694 umol/mmol creatinineAdult (>18 years old)BothNormal details
    UrineDetected and Quantified0.00393 umol/mmol creatinineAdult (>18 years old)BothNormal details
    UrineDetected and Quantified0.00555 umol/mmol creatinineAdult (>18 years old)BothNormal details
    UrineDetected and Quantified0.00733 umol/mmol creatinineAdult (>18 years old)BothNormal details
    UrineExpected but not Quantified Not AvailableNot AvailableNot Available
      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
      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. [PubMed: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. [PubMed: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. [PubMed:10879486 ]