AFCDB: Myricetin (FDB012724)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:19 UTC

Update date

2020-09-17 15:39:06 UTC

Primary ID

FDB012724

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Myricetin

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 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. Outside of the human body, 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. This could make myricetin a potential biomarker for the consumption of these foods.

CAS Number

529-44-2

Structure

MOL SDF PDB SMILES InChI

Synonyms

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	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C15H10O8

IUPAC name

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

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 Key

IKMDFBPHZNJCSN-UHFFFAOYSA-N

Isomeric SMILES

OC1=CC(O)=C2C(OC(=C(O)C2=O)C2=CC(O)=C(O)C(O)=C2)=C1

Average Molecular Weight

318.2351

Monoisotopic Molecular Weight

318.037567296

Classification

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 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biological:

Animal

Plant:

Biological location:

Biofluid and excreta:

Blood

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	C 56.61%; H 3.17%; O 40.22%	DFC
Melting Point	Mp 357-360° dec.	DFC
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	Myricetin, non-derivatized, GC-MS Spectrum	splash10-000t-0943100000-fa00c6f71be0c6675599	Spectrum
GC-MS	Myricetin, 6 TMS, GC-MS Spectrum	splash10-005c-2954350000-46c24c9458aadfd2a711	Spectrum
GC-MS	Myricetin, non-derivatized, GC-MS Spectrum	splash10-000t-0943100000-fa00c6f71be0c6675599	Spectrum
GC-MS	Myricetin, non-derivatized, GC-MS Spectrum	splash10-005c-2954350000-46c24c9458aadfd2a711	Spectrum
Predicted GC-MS	Myricetin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00kr-0962000000-771167ae1d9403c88d56	Spectrum
Predicted GC-MS	Myricetin, 5 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0bt9-1021109000-c6b0cd1ae27d5b8c74c1	Spectrum
Predicted GC-MS	Myricetin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 5V, Positive	splash10-014i-0009000000-99c784d42ece911ecc13	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-014i-0907000000-0b4ff7a72a459baa829c	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0pbi-0900000000-b492f594bdca4c8132a0	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-0uxr-0950000000-55c90a0d932630c6d644	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-014i-0329000000-43069a5bf007fae18a27	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Positive	splash10-014i-0009000000-2b98dfcc4f869be90285	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Negative	splash10-014i-0009104000-6dada42248181a0149f3	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-014i-0009000000-bdbe61e1aba659fd27d2	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-014i-0009000000-bdbe61e1aba659fd27d2	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-014i-0009000000-2499e01afe3b3651b392	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-014i-0009000000-bdbe61e1aba659fd27d2	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-014i-0009000000-35024ff951cd0ca242e4	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-014r-0079000000-b798a1be942ffa6396d2	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-014i-0009000000-2499e01afe3b3651b392	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-0gb9-2951000000-55186f59f5d6ec659c2d	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-014i-0009000000-7494718b3a96d5664b53	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-014i-0209000000-2b4763ddb9eb888c9bfd	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0v09-0901000000-6861fe274e8b0b6b663e	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0udr-0900000000-e982d07ed9f6838c4ee0	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0009000000-9a84f52c6a2f1aaec1a7	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0219000000-36b340f32ee87232a4d1	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0v0a-5931000000-56b06c0109d323a15bc9	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0009000000-7c52125f5ee8fbc51ba0	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0229000000-413e7e87d4aaf205ca23	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-066u-5930000000-ebd17a876ef4c64d13c0	2015-05-27	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Methanol, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Methanol, experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

309

DrugBank ID

DB02375

HMDB ID

HMDB02755

CRC / DFC (Dictionary of Food Compounds) ID

HKC26-K:HKC26-K

EAFUS ID

Not Available

Dr. Duke ID

MYRICETIN

BIGG ID

Not Available

KNApSAcK ID

C00001071

HET ID

MYC

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Myricetin

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

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Descriptor	ID	Definition	Reference
allelochemic			DUKE
anti allergenic	50857	A drug used to treat allergic reactions.	DUKE
anti bacterial	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti feedant			DUKE
anti gastric			DUKE
anti gingivitic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti gonadotrophic			DUKE
anti histaminic	37956	Histamine antagonists are the drugs that bind to but do not activate histamine receptors, thereby blocking the actions of histamine or histamine agonists.	DUKE
anti HIV	22587	A substance that destroys or inhibits replication of viruses.	DUKE
anti inflammatory	35472	A substance that reduces or suppresses inflammation.	DUKE

Showing 1 to 10 of 33 entries

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

show

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.

Myricetin (FDB012724)

Structure for FDB012724 (Myricetin)