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Isorhamnetin (FDB000604)

Record Information
Version1.0
Creation date2010-04-08 22:04:38 UTC
Update date2020-09-17 15:39:04 UTC
Primary IDFDB000604
Secondary Accession Numbers
  • FDB031348
Chemical Information
FooDB NameIsorhamnetin
DescriptionIsorhamnetin, also known as 3-methylquercetin, 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, isorhamnetin is considered to be a flavonoid lipid molecule. A monomethoxyflavone that is quercetin in which the hydroxy group at position 3' is replaced by a methoxy group. Isorhamnetin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Isorhamnetin exists in all eukaryotes, ranging from yeast to humans. Isorhamnetin is a bitter tasting compound. Outside of the human body, Isorhamnetin is found, on average, in the highest concentration within a few different foods, such as parsley, green bell peppers, and dills and in a lower concentration in romaine lettuces, chinese cabbages, and pears. Isorhamnetin has also been detected, but not quantified in, several different foods, such as lemons, agars, chickpea, apples, and cucurbita. This could make isorhamnetin a potential biomarker for the consumption of these foods.
CAS Number480-19-3
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.15 g/LALOGPS
logP1.96ALOGPS
logP2.3ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)6.38ChemAxon
pKa (Strongest Basic)-4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area116.45 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity81.34 m³·mol⁻¹ChemAxon
Polarizability30.58 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC16H12O7
IUPAC name3,5,7-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-chromen-4-one
InChI IdentifierInChI=1S/C16H12O7/c1-22-11-4-7(2-3-9(11)18)16-15(21)14(20)13-10(19)5-8(17)6-12(13)23-16/h2-6,17-19,21H,1H3
InChI KeyIZQSVPBOUDKVDZ-UHFFFAOYSA-N
Isomeric SMILESCOC1=C(O)C=CC(=C1)C1=C(O)C(=O)C2=C(O)C=C(O)C=C2O1
Average Molecular Weight316.2623
Monoisotopic Molecular Weight316.058302738
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.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavones
Direct ParentFlavonols
Alternative Parents
Substituents
  • 3p-methoxyflavonoid-skeleton
  • 3-hydroxyflavone
  • 3-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Hydroxyflavonoid
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • Methoxyphenol
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Pyranone
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Pyran
  • Vinylogous acid
  • Heteroaromatic compound
  • Ether
  • Organoheterocyclic compound
  • Oxacycle
  • Polyol
  • Organic oxygen compound
  • Organooxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Foods
  • Cocoa and cocoa products

    • Grains:

    Nuts and legumes:

    Fruits and vegetables:

    Fats and oils:

    Beverages:

    Physico-Chemical Properties
    Physico-Chemical Properties - Experimental
    PropertyValueReference
    Physical stateSolid
    Physical DescriptionNot Available
    Mass CompositionC 60.76%; H 3.82%; O 35.41%DFC
    Melting PointMp 305° dec.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
    EI-MS/GC-MS
    TypeDescriptionSplash KeyView
    GC-MSIsorhamnetin, non-derivatized, GC-MS Spectrumsplash10-014i-2219000000-20feeef38553ee7cdd29Spectrum
    GC-MSIsorhamnetin, non-derivatized, GC-MS Spectrumsplash10-014i-2219000000-20feeef38553ee7cdd29Spectrum
    Predicted GC-MSIsorhamnetin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000i-0591000000-2e1f6e28bf0d47d5e240Spectrum
    Predicted GC-MSIsorhamnetin, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-001u-0041090000-7e13d91dc4b2bd93fc17Spectrum
    Predicted GC-MSIsorhamnetin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    MS/MS
    TypeDescriptionSplash KeyView
    MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-0udi-0394000000-f903b8df9b79e6a94f442017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Negativesplash10-0udi-0956000000-6286c6784746c9eba0e82017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0gb9-0219000000-c620190cc3878a4242f92017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0zfr-1941000000-10313269e61a0584f37f2017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0gb9-0109000000-082620470bd7fd8a68972017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0ufr-0491000000-da6ec11ed89cc64a79722017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-014i-0139000000-141b68c1e564685b35ce2017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-014i-0139000000-8fa57905e16cdfcc4e9e2017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0udi-0493000000-2b88769e97319b5f076c2021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-0udi-1940000000-51e0d426523f81faa98b2021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0gb9-0009000000-caca1c7784ed9828dfb42021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-0233e63233dadf52ffc52021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0zfr-0952000000-13e1d438b3f800cfc18a2021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0gb9-0209000000-89d7fc697d82018c12282021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0gb9-0209000000-405d086d8e4de2b975b12021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 50V, Negativesplash10-0a4i-1910000000-170b80b866f2075e44e92021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-014i-0029000000-a9da21c499e339f09ac62021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0udi-0493000000-14bbb49d59d91543a76e2021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-014i-0029000000-3458ddb4f7ba64eb81c82021-09-20View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0019000000-bb7cbcffdd9f296b6b9b2016-08-03View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0079000000-c73663231834b1b1b79a2016-08-03View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uds-3790000000-3b8ca78684ffcba51bf12016-08-03View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-57dd2505d869c8f411dc2016-08-03View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0169000000-38b50b4081dff638023b2016-08-03View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0frb-3890000000-3525a3f4676b6a964b712016-08-03View Spectrum
    NMRNot Available
    ChemSpider ID4444973
    ChEMBL IDCHEMBL379064
    KEGG Compound IDC10084
    Pubchem Compound ID5281654
    Pubchem Substance IDNot Available
    ChEBI ID6052
    Phenol-Explorer ID318
    DrugBank IDNot Available
    HMDB IDHMDB02655
    CRC / DFC (Dictionary of Food Compounds) IDBFD21-N:BFD21-N
    EAFUS IDNot Available
    Dr. Duke IDISORHAMNETIN|3'-METHOXY-QUERCETIN
    BIGG IDNot Available
    KNApSAcK IDC00004635
    HET IDNot Available
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    Flavornet IDNot Available
    GoodScent IDNot Available
    SuperScent IDNot Available
    Wikipedia IDIsorhamnetin
    Phenol-Explorer Metabolite ID318
    Duplicate IDSNot Available
    Old DFC IDSNot Available
    Associated Foods
    FoodContent Range AverageReference
    FoodReference
    Biological Effects and Interactions
    Health Effects / Bioactivities
    DescriptorIDDefinitionReference
    anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
    anti histaminic37956 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 inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
    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
    anti spasmodic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
    cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
    hepatoprotective62868 Any compound that is able to prevent damage to the liver.DUKE
    monoamine-oxidase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
    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
    quinone-reductase inducerDUKE
    vasodilator35620 A drug used to cause dilation of the blood vessels.DUKE
    tyrosinase inhibitor59997 Any EC 1.14.18.* (oxidoreductase acting on paired donors, miscellaneous compound as one donor, incorporating 1 atom of oxygen) inhibitor that interferes with the action of tyrosinase (monophenol monooxygenase), EC 1.14.18.1, an enzyme that catalyses the oxidation of phenols (such as tyrosine) and is widespread in plants and animals.CHEBI
    anti coagulant50249 An agent that prevents blood clotting.CHEBI
    EnzymesNot Available
    PathwaysNot Available
    MetabolismNot Available
    BiosynthesisNot Available
    Organoleptic Properties
    Flavours
    FlavorCitations
    bitter
    1. Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
    Files
    MSDSshow
    References
    Synthesis ReferenceNot Available
    General ReferenceNot Available
    Content Reference— 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).
    — 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.