Myricetin (CHEM028411)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 00:26:30 UTC
Update Date2016-11-09 01:18:41 UTC
Accession NumberCHEM028411
Identification
Common NameMyricetin
ClassSmall Molecule
DescriptionA hexahydroxyflavone that is flavone substituted by hydroxy groups at positions 3, 3', 4', 5, 5' and 7. It has been isolated from the leaves of Myrica rubra and other plants.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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-oneMeSH, HMDB
3,3’,4’,5,5’,7-HexahydroxyflavonePhytoBank
3,5,7,3’,4’,5’-HexahydroxyflavonePhytoBank
Chemical FormulaC15H10O8
Average Molecular Mass318.235 g/mol
Monoisotopic Mass318.038 g/mol
CAS Registry Number529-44-2
IUPAC Name3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-4H-chromen-4-one
Traditional Namemyricetin
SMILESOC1=CC(O)=C2C(OC(=C(O)C2=O)C2=CC(O)=C(O)C(O)=C2)=C1
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-000t-0943100000-fa00c6f71be0c6675599Spectrum
GC-MSGC-MS Spectrum - GC-MS (6 TMS)splash10-005c-2954350000-46c24c9458aadfd2a711Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000t-0943100000-fa00c6f71be0c6675599Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-005c-2954350000-46c24c9458aadfd2a711Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00kr-0962000000-771167ae1d9403c88d56Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positivesplash10-0bt9-1021109000-c6b0cd1ae27d5b8c74c1Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 5V, Positivesplash10-014i-0009000000-99c784d42ece911ecc13Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-014i-0907000000-0b4ff7a72a459baa829cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0pbi-0900000000-b492f594bdca4c8132a0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0uxr-0950000000-55c90a0d932630c6d644Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-014i-0329000000-43069a5bf007fae18a27Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Positivesplash10-014i-0009000000-2b98dfcc4f869be90285Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Negativesplash10-014i-0009104000-6dada42248181a0149f3Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-014i-0009000000-bdbe61e1aba659fd27d2Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-014i-0009000000-bdbe61e1aba659fd27d2Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-014i-0009000000-2499e01afe3b3651b392Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-014i-0009000000-bdbe61e1aba659fd27d2Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-014i-0009000000-35024ff951cd0ca242e4Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-014r-0079000000-b798a1be942ffa6396d2Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-014i-0009000000-2499e01afe3b3651b392Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0gb9-2951000000-55186f59f5d6ec659c2dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-0009000000-7494718b3a96d5664b53Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-0209000000-2b4763ddb9eb888c9bfdSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0v09-0901000000-6861fe274e8b0b6b663eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udr-0900000000-e982d07ed9f6838c4ee0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0009000000-9a84f52c6a2f1aaec1a7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0219000000-36b340f32ee87232a4d1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0v0a-5931000000-56b06c0109d323a15bc9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-7c52125f5ee8fbc51ba0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0229000000-413e7e87d4aaf205ca23Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-066u-5930000000-ebd17a876ef4c64d13c0Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB02375
HMDB IDHMDB0002755
FooDB IDFDB012724
Phenol Explorer ID309
KNApSAcK IDC00001071
BiGG IDNot Available
BioCyc IDMYRICETIN
METLIN ID3448
PDB IDNot Available
Wikipedia LinkMyricetin
Chemspider ID4444991
ChEBI ID18152
PubChem Compound ID5281672
Kegg Compound IDC10107
YMDB IDYMDB01754
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=19407970
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=19778600
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=22482362
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=23099505
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=23232835
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=23265454
7. De Israilev, Lidia R. A.; Del Pero de Martinez, Maria A.; Seeligmann, Peter. Myricetin in Tagetes: chemosystematic significance. Phytochemistry (1991), 30(12), 4037-8.
8. 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.
9. 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.