Record Information
Version1.0
Creation date2010-04-08 22:05:25 UTC
Update date2018-05-28 22:41:01 UTC
Primary IDFDB002536
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameQuercetin 3-rutinoside
DescriptionFirst isolated from Ruta graveolens (rue). Bioflavanoid. Quercetin 3-rutinoside is found in many foods, some of which are tea, bilberry, common oregano, and lemon grass.
CAS Number153-18-4
Structure
Thumb
Synonyms
SynonymSource
3-[[6-O-(6-Deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl]oxy]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-oneChEBI
3-RhamnoglucosylquercetinChEBI
3-Rutinosyl quercetinChEBI
PhytomelinChEBI
Quercetin 3-rutinosideChEBI
Quercetin-3-rutinosideChEBI
RutosideChEBI
VenorutonKegg
3-[[6-O-(6-Deoxy-a-L-mannopyranosyl)-b-D-glucopyranosyl]oxy]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-oneGenerator
3-[[6-O-(6-Deoxy-α-L-mannopyranosyl)-β-D-glucopyranosyl]oxy]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-oneGenerator
3,3',4',5,7-Pentahydroxyflavone-3-rutinosideHMDB
3-Rhamnoglucoside OF 3,3',4',5,7-pentahydroxyflavoneHMDB
beta-Quercetin-3-rutinosideHMDB
BioflavonoidHMDB
BirutanHMDB
Birutan forteHMDB
BirutinHMDB
EldrinHMDB
GlobulariacitrinHMDB
GlobularicitrinHMDB
IlixanthinHMDB
MelinHMDB
MyrticolorinHMDB
NeoisorutinHMDB
OsyritrinHMDB
OxyritinHMDB
PaliurosideHMDB
Quercetin 3-O-beta-D-rutinosideHMDB
Quercetin 3-O-beta-delta-rutinosideHMDB
Quercetin 3-O-rutinosideHMDB
Quercetin 3-rhamnoglucosideHMDB
Quercetin rhamnoglucosineHMDB
Quercetin-3beta-rutinosideHMDB
Quercetol 3-rhamnoglucosideHMDB
Quercitin 3-rutinosideHMDB
RUTHMDB
RutabionHMDB
Rutin trihydrateHMDB
RutineHMDB
Rutinic acidHMDB
Rutinion acidHMDB
RutinumHMDB
RutosidHMDB
RutosidoHMDB
RutosidumHMDB
RutozydHMDB
SophorinHMDB
TanrutinHMDB
ViolaquercitrinHMDB
Vitamin pHMDB
3-Rhamnosyl-glucosyl quercetinHMDB
Quercetin 3 rutinosideHMDB
Quercetin, 3-rhamnosyl-glucosylHMDB
RutinKEGG
Hydroxyethylrutosidebiospider
Osyritindb_source
Quercetin 3-b-D-rutinosidedb_source
Quercetin 3-O-[beta-L-rhamnosyl-(1->6)-beta-D-glucoside]biospider
Rutiniondb_source
Rutoside, BAN, INNdb_source
Sophorin?db_source
Vitamin P?db_source
Predicted Properties
PropertyValueSource
Water Solubility3.54 g/LALOGPS
logP0.15ALOGPS
logP-0.87ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)6.37ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area265.52 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity140.15 m³·mol⁻¹ChemAxon
Polarizability57.08 ųChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC27H30O16
IUPAC name2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-4H-chromen-4-one
InChI IdentifierInChI=1S/C27H30O16/c1-8-17(32)20(35)22(37)26(40-8)39-7-15-18(33)21(36)23(38)27(42-15)43-25-19(34)16-13(31)5-10(28)6-14(16)41-24(25)9-2-3-11(29)12(30)4-9/h2-6,8,15,17-18,20-23,26-33,35-38H,7H2,1H3/t8-,15+,17-,18+,20+,21-,22+,23+,26+,27-/m0/s1
InChI KeyIKGXIBQEEMLURG-NVPNHPEKSA-N
Isomeric SMILESC[C@@H]1O[C@@H](OC[C@H]2O[C@@H](OC3=C(OC4=CC(O)=CC(O)=C4C3=O)C3=CC(O)=C(O)C=C3)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O
Average Molecular Weight610.5175
Monoisotopic Molecular Weight610.153384912
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
  • 3'-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • O-glycosyl compound
  • Glycosyl compound
  • Disaccharide
  • Chromone
  • 1-benzopyran
  • Benzopyran
  • Catechol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • 1-hydroxy-4-unsubstituted benzenoid
  • Pyranone
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Oxane
  • Vinylogous acid
  • Heteroaromatic compound
  • Secondary alcohol
  • Organoheterocyclic compound
  • Oxacycle
  • Acetal
  • Polyol
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
OntologyShould have ontology for this compound
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 53.12%; H 4.95%; O 41.93%DFC
Melting PointMp 214-215 dec. (anhyd.)DFC
Boiling PointNot Available
Experimental Water Solubility0.125 mg/mLMERCK INDEX (1989)
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]23D +13.82 (EtOH)DFC
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, Positivesplash10-052p-7581190000-d9593c696e6c6e2454edView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-0000009000-a6b8403579a83c69506bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-03di-0002009000-ffacf122369038644c02View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0w29-5009015000-f74826ba5205775d12b8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 5V, Positivesplash10-03di-0003109000-85542c3510756d258e11View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Positivesplash10-0ik9-0008109000-f0d08078ad4b887cce0dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Negativesplash10-0a4i-0000009000-f07697affe03ff93dad3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Positivesplash10-0udi-0009000000-1b117e308c1ab00aa4a7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0a4i-0000009000-270308e3f77a0404dea8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0a4i-0010009000-f94b0edacf4c3bc9c9e3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-0udi-0049001000-8327d9d15b0d22a0c968View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0a4i-0000009000-270308e3f77a0404dea8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0a4i-0010009000-f94b0edacf4c3bc9c9e3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-0udi-0049001000-8327d9d15b0d22a0c968View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0udi-0009100000-dfc0a2b72193a5072ddeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0a4i-0000009000-dd163a2a17fe559c3482View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0a4i-0000009000-7b408d31853f85c12619View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0a4i-0001009000-3a559cbd175dfd7bafc9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0009005000-a090fd87b44b66b9f0c0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0009000000-8454cc7afaccaa2be7acView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0139143000-0b231bbaf0f8cd578ce9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0249200000-5766b78c90749219634cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udr-1955000000-49ac7b74c557179bbcaeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0pb9-5539337000-13a750c25d00b7185c08View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-3539010000-707593795636ef3841c1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-3966000000-61676ecb8f5b5e514760View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
ChemSpider ID4444362
ChEMBL IDCHEMBL226335
KEGG Compound IDC05625
Pubchem Compound ID5280805
Pubchem Substance IDNot Available
ChEBI ID28527
Phenol-Explorer ID296
DrugBank IDDB01698
HMDB IDHMDB03249
CRC / DFC (Dictionary of Food Compounds) IDCMH35-W:CMH35-W
EAFUS ID3346
Dr. Duke IDQUERCETIN-3-RHAMNOGLUCOSIDE|QUERCETIN-3-O-BETA-D-RUTOSIDE|QUERCETIN-3-O-RUTINOSIDE|QUERCETIN-3-0-RUTINOSIDE| QUERCITIN-3-RUTINOSIDE|RUTIN|RUTOSIDE
BIGG IDNot Available
KNApSAcK ID3346
HET IDRUT
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDRutin
Phenol-Explorer Metabolite ID296
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
5-hydroxytryptamine inhibitor48279 Drugs that bind to but do not activate serotonin receptors, thereby blocking the actions of serotonin or serotonergic agonists.DUKE
aldehyde-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
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
allelochemicDUKE
anti aggregantDUKE
anti allergic50857 A drug used to treat allergic reactions.DUKE
anti apoplectic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti atherogenic38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
anti atherosclerotic38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti cancer35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti capillary-fragilityDUKE
anti cataract52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti clastogenDUKE
anti convulsant52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti CVIDUKE
anti dementia52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti dermatitic50177 A drug used to treat or prevent skin disorders or for the routine care of skin.DUKE
anti diabetic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti edemicDUKE
anti erythemic50177 A drug used to treat or prevent skin disorders or for the routine care of skin.DUKE
anti feedantDUKE
anti glaucomicDUKE
anti hematuricDUKE
anti hemorrhoidal52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti hepatotoxic62868 Any compound that is able to prevent damage to the liver.DUKE
anti herpetic22587 A substance that destroys or inhibits replication of viruses.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 hypertensive52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
anti malarial33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti melanomic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti metastatic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti mutagenicDUKE
anti nephritic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti nociceptive35470 A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.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 peroxidantDUKE
anti plateletDUKE
anti proliferantDUKE
anti protozoal33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti purpuric50177 A drug used to treat or prevent skin disorders or for the routine care of skin.DUKE
anti radicularDUKE
anti spasmodic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti sunburn52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti thrombogenic50248 Drug that acts on blood and blood-forming organs and those that affect the hemostatic system.DUKE
anti thyroidDUKE
anti trypanosomic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
antitumor promoter35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti ulcer49201 One of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract.DUKE
anti varicose52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti viral22587 A substance that destroys or inhibits replication of viruses.DUKE
apoptoticDUKE
cAMP-phosphodiesterase 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
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
capillariprotectiveDUKE
catabolicDUKE
catechol O-methyltransferase inhibitor48406 An EC 2.1.1.* (methyltransferase) inhibitor that interferes with the action of catechol O-methyltransferase (EC 2.1.1.6).DUKE
chemopreventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
cholereticDUKE
cytoprotectiveDUKE
diuretic35498 An agent that promotes the excretion of urine through its effects on kidney function.DUKE
estrogenicDUKE
hemostatDUKE
hepatomagenicDUKE
hepatoprotective62868 Any compound that is able to prevent damage to the liver.DUKE
hypocholesterolemicDUKE
hypotensiveDUKE
immunomodulator50846 Biologically active substance whose activity affects or plays a role in the functioning of the immune system.DUKE
insecticide24852 Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.DUKE
Insectiphile24852 Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.DUKE
juvabionalDUKE
larvistatDUKE
lipoxygenase inhibitor35856 A compound or agent that combines with lipoxygenase and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of the icosanoid products hydroxyicosatetraenoic acid and various leukotrienes.DUKE
mutagenicDUKE
myoprotectiveDUKE
myorelaxantDUKE
oviposition stimulantDUKE
platelet aggregation factor inhibitor50427 A drug or agent which antagonizes or impairs any mechanism leading to blood platelet aggregation, whether during the phases of activation and shape change or following the dense-granule release reaction and stimulation of the prostaglandin-thromboxane system.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
protisticideDUKE
radioprotective35232 Any pharmaceutical compound containing a radioisotope.DUKE
sunscreen52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
topoisomerase-II inhibitor50750 A topoisomerase inhibitor that inhibits DNA topoisomerase (ATP-hydrolysing), EC 5.99.1.3 (topoisomerase II), which catalyses ATP-dependent breakage of both strands of DNA, passage of the unbroken strands through the breaks, and rejoining of the broken strands.DUKE
vasodilator35620 A drug used to cause dilation of the blood vessels.DUKE
vasopressorDUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot 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.
— 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.