Record Information
Version1.0
Creation date2010-04-08 22:10:19 UTC
Update date2018-01-23 19:24:57 UTC
Primary IDFDB012726
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameMyricetin 3-rhamnoside
DescriptionMyricitrin is a chemical compound. It can be isolated from the root bark of Myrica cerifera (Bayberry, a small tree native to North America). Myricetin 3-rhamnoside is found in many foods, some of which are common grape, black walnut, highbush blueberry, and lentils.
CAS Number17912-87-7
Structure
Thumb
Synonyms
SynonymSource
Flavone,3,3',4',5,5',7-hexahydroxy-,3-rhamnosideHMDB
Myricetin 3-O-alpha-L-rhamnopyranosideHMDB
Myricetin 3-O-alpha-L-rhamnosideHMDB
Myricetin 3-O-L-rhamnosideHMDB
Myricetin 3-O-rhamnosideHMDB
Myricetin 3-rhamnosideHMDB
Myricetin-3-O-alpha-L-rhamnosideHMDB
Myricetol 3-rhamnosideHMDB
MyricetrinHMDB
Myricitrin (8ci)HMDB
MyricitrineHMDB
MyricitrosideHMDB
Rhamnoside,myricetin-3HMDB
Myricitrindb_source
Predicted Properties
PropertyValueSource
Water Solubility2.43 g/LALOGPS
logP1.18ALOGPS
logP0.6ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)6.43ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area206.6 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity109.71 m³·mol⁻¹ChemAxon
Polarizability43.43 ųChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC21H20O12
IUPAC name5,7-dihydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-2-(3,4,5-trihydroxyphenyl)-4H-chromen-4-one
InChI IdentifierInChI=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 KeyDCYOADKBABEMIQ-UHFFFAOYSA-N
Isomeric SMILESCC1OC(OC2=C(OC3=CC(O)=CC(O)=C3C2=O)C2=CC(O)=C(O)C(O)=C2)C(O)C(O)C1O
Average Molecular Weight464.3763
Monoisotopic Molecular Weight464.095476104
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.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid-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 FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 54.32%; H 4.34%; O 41.34%DFC
Melting PointMp 194-197°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0k9b-9201300000-d10e32fc5a1d0c76806fView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-014i-9400007000-64569a12a871673daba9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0109600000-ebb1fb40483758f777abView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0209000000-e344b10d0f1020c27096View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udr-2926000000-7decfb86b27dd94e53c6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0109600000-ebb1fb40483758f777abView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0209000000-e344b10d0f1020c27096View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udr-2926000000-7decfb86b27dd94e53c6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03xr-2207900000-d36fac331dffea5d2f42View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-1339200000-33bd246d971e42c5ad27View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0170-5964000000-7bd9b72230384ddf2e0bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03xr-2207900000-d36fac331dffea5d2f42View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-1339200000-33bd246d971e42c5ad27View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0170-5964000000-7bd9b72230384ddf2e0bView in MoNA
ChemSpider ID4508981
ChEMBL IDNot Available
KEGG Compound IDC10108
Pubchem Compound ID5352000
Pubchem Substance IDNot Available
ChEBI ID544021
Phenol-Explorer ID327
DrugBank IDNot Available
HMDB IDHMDB34360
CRC / DFC (Dictionary of Food Compounds) IDHKC26-K:HKC30-H
EAFUS ID2624
Dr. Duke IDMYRICITRIN
BIGG IDNot Available
KNApSAcK IDC00005730
HET IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDMyricitrin
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
aldose reductase inhibitor48550 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 bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
anti mutagenicDUKE
antioxidant22586 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 promoter35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
candidicideDUKE
cholereticDUKE
diuretic35498 An agent that promotes the excretion of urine through its effects on kidney function.DUKE
paramecicideDUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
protisticideDUKE
spermicideDUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— 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.
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.