Showing Compound Myricetin 3-rhamnoside (FDB012726)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:19 UTC

Update date

2019-11-26 03:07:28 UTC

Primary ID

FDB012726

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Myricetin 3-rhamnoside

Description

Myricetin 3-rhamnoside belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position. Myricetin 3-rhamnoside is found, on average, in the highest concentration within highbush blueberries (Vaccinium corymbosum) and lentils (Lens culinaris). Myricetin 3-rhamnoside has also been detected, but not quantified in, several different foods, such as summer grapes (Vitis aestivalis), rubus (blackberry, raspberry), common hazelnuts (Corylus avellana), sapodillas (Manilkara zapota), and black walnuts (Juglans nigra). This could make myricetin 3-rhamnoside a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Myricetin 3-rhamnoside.

CAS Number

17912-87-7

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Flavone,3,3',4',5,5',7-hexahydroxy-,3-rhamnoside	HMDB
Myricetin 3-O-alpha-L-rhamnopyranoside	HMDB
Myricetin 3-O-alpha-L-rhamnoside	HMDB
Myricetin 3-O-L-rhamnoside	HMDB
Myricetin 3-O-rhamnoside	HMDB
Myricetin 3-rhamnoside	HMDB
Myricetin-3-O-alpha-L-rhamnoside	HMDB
Myricetol 3-rhamnoside	HMDB
Myricetrin	HMDB
Myricitrin (8ci)	HMDB
Myricitrine	HMDB
Myricitroside	HMDB
Rhamnoside,myricetin-3	HMDB
Myricitrin	db_source

Predicted Properties

Property	Value	Source
Water Solubility	2.43 g/L	ALOGPS
logP	1.18	ALOGPS
logP	0.6	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	6.43	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	206.6 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	109.71 m³·mol⁻¹	ChemAxon
Polarizability	43.43 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C21H20O12

IUPAC name

5,7-dihydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-2-(3,4,5-trihydroxyphenyl)-4H-chromen-4-one

InChI Identifier

InChI=1S/C21H20O12/c1-6-14(26)17(29)18(30)21(31-6)33-20-16(28)13-9(23)4-8(22)5-12(13)32-19(20)7-2-10(24)15(27)11(25)3-7/h2-6,14,17-18,21-27,29-30H,1H3

InChI Key

DCYOADKBABEMIQ-UHFFFAOYSA-N

Isomeric SMILES

CC1OC(OC2=C(OC3=CC(O)=CC(O)=C3C2=O)C2=CC(O)=C(O)C(O)=C2)C(O)C(O)C1O

Average Molecular Weight

464.3763

Monoisotopic Molecular Weight

464.095476104

Classification

Description

Belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-3-O-glycosides

Alternative Parents

Substituents

Flavonoid-3-o-glycoside
Hydroxyflavonoid
Flavone
7-hydroxyflavonoid
5-hydroxyflavonoid
4'-hydroxyflavonoid
3'-hydroxyflavonoid
Hexose monosaccharide
Chromone
Glycosyl compound
O-glycosyl compound
Benzopyran
1-benzopyran
Benzenetriol
Pyrogallol derivative
Phenol
1-hydroxy-4-unsubstituted benzenoid
Pyranone
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Pyran
Monosaccharide
Oxane
Vinylogous acid
Heteroaromatic compound
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Polyol
Acetal
Organic oxide
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biological:

Plant:

Fabaceae

Biological location:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Role

Biological role:

Nutrient

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 54.32%; H 4.34%; O 41.34%	DFC
Melting Point	Mp 194-197°	DFC
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Myricetin 3-rhamnoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0k9b-9201300000-d10e32fc5a1d0c76806f	Spectrum
Predicted GC-MS	Myricetin 3-rhamnoside, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-014i-9400007000-64569a12a871673daba9	Spectrum
Predicted GC-MS	Myricetin 3-rhamnoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Myricetin 3-rhamnoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Myricetin 3-rhamnoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Myricetin 3-rhamnoside, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Myricetin 3-rhamnoside, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Myricetin 3-rhamnoside, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Myricetin 3-rhamnoside, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Myricetin 3-rhamnoside, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Myricetin 3-rhamnoside, TMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Myricetin 3-rhamnoside, TMS_1_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Myricetin 3-rhamnoside, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Myricetin 3-rhamnoside, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Myricetin 3-rhamnoside, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Myricetin 3-rhamnoside, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Myricetin 3-rhamnoside, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Myricetin 3-rhamnoside, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Myricetin 3-rhamnoside, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Myricetin 3-rhamnoside, TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Myricetin 3-rhamnoside, TMS_2_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Myricetin 3-rhamnoside, TMS_2_10, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Myricetin 3-rhamnoside, TMS_2_11, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Myricetin 3-rhamnoside, TMS_2_12, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Myricetin 3-rhamnoside, TMS_2_13, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0109600000-ebb1fb40483758f777ab	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0209000000-e344b10d0f1020c27096	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udr-2926000000-7decfb86b27dd94e53c6	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0109600000-ebb1fb40483758f777ab	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0209000000-e344b10d0f1020c27096	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udr-2926000000-7decfb86b27dd94e53c6	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03xr-2207900000-d36fac331dffea5d2f42	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014j-1339200000-33bd246d971e42c5ad27	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0170-5964000000-7bd9b72230384ddf2e0b	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03xr-2207900000-d36fac331dffea5d2f42	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014j-1339200000-33bd246d971e42c5ad27	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0170-5964000000-7bd9b72230384ddf2e0b	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0000900000-ede760d3092419a25e9d	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0300900000-54bc9fe47fd4524c0d68	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0gbl-1910200000-32350626533e5314ca32	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0000900000-efd108638fa903352a90	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0000900000-d5904d6fa0706b78e735	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0gb9-1901400000-7a5f7075c27aee4ffc7b	2021-09-25	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

4508981

ChEMBL ID

Not Available

KEGG Compound ID

C10108

Pubchem Compound ID

5352000

Pubchem Substance ID

Not Available

ChEBI ID

544021

Phenol-Explorer ID

327

DrugBank ID

Not Available

HMDB ID

HMDB34360

CRC / DFC (Dictionary of Food Compounds) ID

HKC26-K:HKC30-H

EAFUS ID

2624

Dr. Duke ID

MYRICITRIN

BIGG ID

Not Available

KNApSAcK ID

C00005730

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Myricitrin

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
aldose reductase inhibitor	48550	An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21).	DUKE
anti bacterial	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti inflammatory	35472	A substance that reduces or suppresses inflammation.	DUKE
anti mutagenic			DUKE
antioxidant	22586	A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.	DUKE
antitumor promoter	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
candidicide			DUKE
choleretic			DUKE
diuretic	35498	An agent that promotes the excretion of urine through its effects on kidney function.	DUKE
paramecicide			DUKE
pesticide	25944	Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.	DUKE
protisticide			DUKE
spermicide			DUKE