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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 15:12:08 UTC
Update Date2021-09-07 16:45:34 UTC
HMDB IDHMDB0002755
Secondary Accession Numbers
  • HMDB02755
Metabolite Identification
Common NameMyricetin
DescriptionMyricetin, also known as cannabiscetin or myricetol, belongs to the class of organic compounds known as flavonols. Flavonols are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position. Thus, myricetin is considered to be a flavonoid lipid molecule. A hexahydroxyflavone that is flavone substituted by hydroxy groups at positions 3, 3', 4', 5, 5' and 7. Myricetin is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Myricetin is found, on average, in the highest concentration within a few different foods, such as common walnuts, carobs, and fennels and in a lower concentration in welsh onions, yellow bell peppers, and jutes. Myricetin has also been detected, but not quantified in several different foods, such as napa cabbages, sesames, mixed nuts, lichee, and garden cress.
Structure
Data?1585325983
Synonyms
ValueSource
3,3',4',5,5',7-HexahydroxyflavoneChEBI
3,5,7,3',4',5'-HexahydroxyflavoneChEBI
CannabiscetinChEBI
MyricetolChEBI
3,3',4',5,5',7-Hexahydroxy-(8ci)- flavoneHMDB
3,5,7-Trihydroxy-2-(3,4,5-trihydroxyphenyl)-4H-1-benzopyran-4-oneHMDB
Chemical FormulaC15H10O8
Average Molecular Weight318.2351
Monoisotopic Molecular Weight318.037567296
IUPAC Name3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-4H-chromen-4-one
Traditional Namemyricetin
CAS Registry Number529-44-2
SMILES
OC1=CC(O)=C2C(OC(=C(O)C2=O)C2=CC(O)=C(O)C(O)=C2)=C1
InChI Identifier
InChI=1S/C15H10O8/c16-6-3-7(17)11-10(4-6)23-15(14(22)13(11)21)5-1-8(18)12(20)9(19)2-5/h1-4,16-20,22H
InChI KeyIKMDFBPHZNJCSN-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as flavonols. Flavonols are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavones
Direct ParentFlavonols
Alternative Parents
Substituents
  • 3-hydroxyflavone
  • 3'-hydroxyflavonoid
  • 3-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Hydroxyflavonoid
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • Benzenetriol
  • Pyrogallol derivative
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Pyranone
  • Benzenoid
  • Monocyclic benzene moiety
  • Pyran
  • Heteroaromatic compound
  • Vinylogous acid
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point357 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.3 g/LALOGPS
logP1.66ALOGPS
logP1.85ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)6.37ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area147.68 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity78.84 m³·mol⁻¹ChemAxon
Polarizability29.47 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-000t-0943100000-fa00c6f71be0c66755992014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (6 TMS)splash10-005c-2954350000-46c24c9458aadfd2a7112014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000t-0943100000-fa00c6f71be0c66755992017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-005c-2954350000-46c24c9458aadfd2a7112017-09-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00kr-0962000000-771167ae1d9403c88d562017-07-27View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positivesplash10-0bt9-1021109000-c6b0cd1ae27d5b8c74c12017-10-06View Spectrum
MSMass Spectrum (Electron Ionization)splash10-000i-0972000000-ecb4c5473903482f0ca42021-09-05View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 5V, Positivesplash10-014i-0009000000-99c784d42ece911ecc132012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-014i-0907000000-0b4ff7a72a459baa829c2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0pbi-0900000000-b492f594bdca4c8132a02012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0uxr-0950000000-55c90a0d932630c6d6442012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-014i-0329000000-43069a5bf007fae18a272012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Positivesplash10-014i-0009000000-2b98dfcc4f869be902852012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Negativesplash10-014i-0009104000-6dada42248181a0149f32012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-014i-0009000000-bdbe61e1aba659fd27d22017-08-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-014i-0009000000-bdbe61e1aba659fd27d22017-08-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-014i-0009000000-2499e01afe3b3651b3922017-08-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-014i-0009000000-bdbe61e1aba659fd27d22017-09-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-014i-0009000000-35024ff951cd0ca242e42017-09-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-014r-0079000000-b798a1be942ffa6396d22017-09-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-014i-0009000000-2499e01afe3b3651b3922017-09-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0gb9-2951000000-55186f59f5d6ec659c2d2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-0009000000-7494718b3a96d5664b532017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-0209000000-2b4763ddb9eb888c9bfd2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0v09-0901000000-6861fe274e8b0b6b663e2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udr-0900000000-e982d07ed9f6838c4ee02017-09-14View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0009000000-9a84f52c6a2f1aaec1a72015-05-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0219000000-36b340f32ee87232a4d12015-05-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0v0a-5931000000-56b06c0109d323a15bc92015-05-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-7c52125f5ee8fbc51ba02015-05-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0229000000-413e7e87d4aaf205ca232015-05-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-066u-5930000000-ebd17a876ef4c64d13c02015-05-27View Spectrum

NMR

Spectrum TypeDescriptionDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2012-12-05View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, predicted)2012-12-05View Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified45.0 (0.62-94.2) uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB02375
Phenol Explorer Compound ID309
FooDB IDFDB012724
KNApSAcK IDC00001071
Chemspider ID4444991
KEGG Compound IDC10107
BioCyc IDMYRICETIN
BiGG IDNot Available
Wikipedia LinkMyricetin
METLIN ID3448
PubChem Compound5281672
PDB IDNot Available
ChEBI ID18152
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
References
Synthesis ReferenceDe Israilev, Lidia R. A.; Del Pero de Martinez, Maria A.; Seeligmann, Peter. Myricetin in Tagetes: chemosystematic significance. Phytochemistry (1991), 30(12), 4037-8.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Noroozi M, Burns J, Crozier A, Kelly IE, Lean ME: Prediction of dietary flavonol consumption from fasting plasma concentration or urinary excretion. Eur J Clin Nutr. 2000 Feb;54(2):143-9. [PubMed:10694785 ]
  2. Noguchi Y, Fukuda K, Matsushima A, Haishi D, Hiroto M, Kodera Y, Nishimura H, Inada Y: Inhibition of Df-protease associated with allergic diseases by polyphenol. J Agric Food Chem. 1999 Aug;47(8):2969-72. [PubMed:10552595 ]

Enzymes

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
Reactions
Myricetin → 6-[2,3-dihydroxy-5-(3,5,7-trihydroxy-4-oxo-4H-chromen-2-yl)phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Myricetin → 6-[2,6-dihydroxy-4-(3,5,7-trihydroxy-4-oxo-4H-chromen-2-yl)phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Myricetin → 6-{[5,7-dihydroxy-4-oxo-2-(3,4,5-trihydroxyphenyl)-4H-chromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Myricetin → 6-{[3,7-dihydroxy-4-oxo-2-(3,4,5-trihydroxyphenyl)-4H-chromen-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Myricetin → 6-{[3,5-dihydroxy-4-oxo-2-(3,4,5-trihydroxyphenyl)-4H-chromen-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails