Showing Compound Card for Eriodictyol (CDB005181)

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Record Information
Version1.0
Created at2020-04-17 19:17:29 UTC
Updated at2020-12-07 19:11:43 UTC
CannabisDB IDCDB005181
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameEriodictyol
DescriptionEriodictyol belongs to the class of organic compounds known as flavanones. Flavanones 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. Thus, eriodictyol is considered to be a flavonoid lipid molecule. Eriodictyol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Eriodictyol has been detected, but not quantified in, several different foods, such as common oregano, common thymes, parsley, sweet basils, and tarragons. This could make eriodictyol a potential biomarker for the consumption of these foods. A tetrahydroxyflavanone that is flavanone substituted by hydroxy groups at positions 5, 7, 3' and 4' respectively. Eriodictyol is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(S)-2-(3,4-Dihydroxyphenyl)-2,3-dihydro-5,7-dihydroxy-4-benzopyroneChEBI
(S)-EriodictyolChEBI
EriodictiolChEBI
(+)-EriodictyolHMDB
(2S)-EriodictyolHMDB
(S)-2,3-DihydroluteolinHMDB
(S)-3',4',5,7-TetrahydroxyflavanoneHMDB
(S)-3’,4’,5,7-TetrahydroxyflavanoneHMDB
3',4',5,7-TetrahydroxyflavanoneHMDB
3’,4’,5,7-TetrahydroxyflavanoneHMDB
(2S)-2-(3,4-Dihydroxyphenyl)-2,3-dihydro-5,7-dihydroxy-4H-1-benzopyran-4-oneHMDB
(2S)-2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-2,3-dihydrochromen-4-oneHMDB
HuazhongilexoneHMDB
Chemical FormulaC15H12O6
Average Molecular Weight288.25
Monoisotopic Molecular Weight288.0634
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=CC(O)=C2C(=O)C[C@H](OC2=C1)C1=CC=C(O)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
Description Belongs to the class of organic compounds known as flavanones. Flavanones 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
  • 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

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateNot Available
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
logP2.15ALOGPS
logP2.53ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)7.85ChemAxon
pKa (Strongest Basic)-5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area107.22 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity73.27 m³·mol⁻¹ChemAxon
Polarizability27.33 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSEriodictyol, 5 TMS, GC-MS Spectrumsplash10-00o3-2964120000-760c54cbe3d97e214b89Spectrum
GC-MSEriodictyol, 1 MEOX; 4 TMS, GC-MS Spectrumsplash10-05i4-3982160000-16d59df001928b3a3494Spectrum
Predicted GC-MSEriodictyol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-06y9-0690000000-250ba7bd6576410f8734Spectrum
Predicted GC-MSEriodictyol, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0imi-2530190000-6bcd43fd8b42301ed166Spectrum
Predicted GC-MSEriodictyol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-000i-0090000000-778b9cb4a7b875c6bbec2017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-052r-0090000000-9178a74a6239d2ef38822017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-052r-0290000000-287f5fa660d816283c292017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0019-0090000000-cb3df3f82944d76bf2242017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0019-0090000000-cb3df3f82944d76bf2242017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-0019-0090000000-cb3df3f82944d76bf2242017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-000i-0090000000-778b9cb4a7b875c6bbec2017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-052r-0090000000-9178a74a6239d2ef38822017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-052r-0290000000-287f5fa660d816283c292017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0019-0090000000-cb3df3f82944d76bf2242017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-000i-0090000000-772ca2fc672ef9668bfa2017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-000i-0920000000-4bc67dc66facd1fa75e52017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0f79-0910000000-c48ad5f3958e9c41f5de2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-000i-0970000000-cb17dd84eda67cc9d6a42017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-000i-0900000000-5c65882b59856d787f672017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0910000000-85200d3bfe0ef9f8c6cf2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0f79-0900000000-8aa62dd381d8e70390e12017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-1900000000-c83d3fbbf98b1c8e768d2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0f79-0950000000-70ad9d5c48c3fd3ab1fe2017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0390000000-0dc39ca84a3e57cc45532016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0980000000-1ccfe66899ea0c7d03a32016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fa9-4900000000-df7958810e2c565408772016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0190000000-a7838f78d4cef436da5f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0390000000-adb9e4c67817a09b2fd02016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0apr-5940000000-9fb4bafc0204f514e65f2016-08-03View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
UDP-glucuronosyltransferase 1-1UGT1A12q37P22309 details
Sulfotransferase 1A3SULT1A3P0DMM9 details
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0005810
DrugBank IDNot Available
Phenol Explorer Compound ID202
FoodDB IDFDB011936
KNApSAcK IDC00000960
Chemspider ID389606
KEGG Compound IDC05631
BioCyc IDCPD-7671
BiGG IDNot Available
Wikipedia LinkEriodictyol
METLIN ID3415
PubChem Compound440735
PDB IDNot Available
ChEBI ID28412
References
General ReferencesNot Available

Enzymes

Enzyme Details
1. UDP-glucuronosyltransferase 1-1
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Enzyme Details
2. Sulfotransferase 1A3
General function:
sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:
SULT1A3
Uniprot ID:
P0DMM9
Molecular weight:
34195.96