Myricetin (YMDB01754)

Identification

YMDB ID

YMDB01754

Name

Myricetin

Species

Saccharomyces cerevisiae

Strain

Brewer's yeast

Description

Myricetin, 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. Based on a literature review a significant number of articles have been published on Myricetin.

Structure

MOL SDF PDB SMILES InChI

Synonyms

3,3',4',5,5',7-Hexahydroxy-(8ci)- flavone
3,3',4',5,5',7-Hexahydroxyflavone
3,5,7-Trihydroxy-2-(3,4,5-trihydroxyphenyl)-4H-1-benzopyran-4-one
3,5,7,3',4',5'-Hexahydroxyflavone
Cannabiscetin
Myricetol
3,3’,4’,5,5’,7-Hexahydroxyflavone
3,5,7,3’,4’,5’-Hexahydroxyflavone

CAS number

529-44-2

Weight

Average: 318.2351
Monoisotopic: 318.037567296

InChI Key

IKMDFBPHZNJCSN-UHFFFAOYSA-N

InChI

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

IUPAC Name

3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-4H-chromen-4-one

Traditional IUPAC Name

myricetin

Chemical Formula

C₁₅H₁₀O₈

SMILES

OC1=CC2=C(C(O)=C1)C(=O)C(O)=C(O2)C1=CC(O)=C(O)C(O)=C1

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.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavones

Direct Parent

Flavonols

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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

7-hydroxyflavonol (CHEBI:18152 )
hexahydroxyflavone (CHEBI:18152 )
flavonols (C10107 )
Flavones and Flavonols (C10107 )
Flavones and Flavonols (LMPK12110001 )

Physical Properties

State

Solid

Charge

Melting point

357 °C

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	0.3 g/L	ALOGPS
logP	1.66	ALOGPS
logP	1.85	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	6.37	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	147.68 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	78.84 m³·mol⁻¹	ChemAxon
Polarizability	29.47 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

Not Available

Organoleptic Properties

Not Available

SMPDB Pathways

Not Available

KEGG Pathways

Not Available

SMPDB Reactions

Not Available

KEGG Reactions

Not Available

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-000t-0943100000-fa00c6f71be0c6675599	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (6 TMS)	splash10-005c-2954350000-46c24c9458aadfd2a711	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-000t-0943100000-fa00c6f71be0c6675599	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-005c-2954350000-46c24c9458aadfd2a711	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00kr-0962000000-771167ae1d9403c88d56	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positive	splash10-0bt9-1021109000-c6b0cd1ae27d5b8c74c1	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 5V, Positive	splash10-014i-0009000000-99c784d42ece911ecc13	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-014i-0907000000-0b4ff7a72a459baa829c	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0pbi-0900000000-b492f594bdca4c8132a0	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-0uxr-0950000000-55c90a0d932630c6d644	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-014i-0329000000-43069a5bf007fae18a27	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Positive	splash10-014i-0009000000-2b98dfcc4f869be90285	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Negative	splash10-014i-0009104000-6dada42248181a0149f3	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-014i-0009000000-bdbe61e1aba659fd27d2	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-014i-0009000000-bdbe61e1aba659fd27d2	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-014i-0009000000-2499e01afe3b3651b392	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-014i-0009000000-bdbe61e1aba659fd27d2	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-014i-0009000000-35024ff951cd0ca242e4	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-014r-0079000000-b798a1be942ffa6396d2	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-014i-0009000000-2499e01afe3b3651b392	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-0gb9-2951000000-55186f59f5d6ec659c2d	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-014i-0009000000-7494718b3a96d5664b53	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-014i-0209000000-2b4763ddb9eb888c9bfd	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0v09-0901000000-6861fe274e8b0b6b663e	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0udr-0900000000-e982d07ed9f6838c4ee0	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0009000000-9a84f52c6a2f1aaec1a7	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0219000000-36b340f32ee87232a4d1	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0v0a-5931000000-56b06c0109d323a15bc9	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0009000000-7c52125f5ee8fbc51ba0	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0229000000-413e7e87d4aaf205ca23	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-066u-5930000000-ebd17a876ef4c64d13c0	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	JSpectraViewer

References

References:

Not Available

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	18152
HMDB ID	HMDB02755
Pubchem Compound ID	5281672
Kegg ID	C10107
ChemSpider ID	4444991
FOODB ID	FDB012724
Wikipedia ID	Myricetin
BioCyc ID	Not Available

Structure for #<Compound:0xac5e8268>