Record Information
Version1.0
Created at2020-04-17 18:53:37 UTC
Updated at2020-11-18 16:39:05 UTC
CannabisDB IDCDB004949
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameRutin
DescriptionRutin, also known as rutoside or phytomelin, 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. Rutin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Rutin is found, on average, in the highest concentration within a few different foods, such as parsley, common buckwheats, and sorrels and in a lower concentration in grape wines, italian sweet red peppers, and nectarines. Rutin has also been detected, but not quantified in, several different foods, such as summer grapes, peachs, broccoli, rosemaries, and tartary buckwheats. This could make rutin a potential biomarker for the consumption of these foods. A rutinoside that is quercetin with the hydroxy group at position C-3 substituted with glucose and rhamnose sugar groups. Rutin is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
Synonyms
ValueSource
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-Rhamnosyl-glucosyl quercetinMeSH
Quercetin 3 rutinosideMeSH
Quercetin, 3-rhamnosyl-glucosylMeSH
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
RutinKEGG
3,3',4',5,7-Pentahydroxyflavone 3-O-rutinosidePhytoBank
3,3’,4’,5,7-Pentahydroxyflavone 3-O-rutinosidePhytoBank
3,3',4',5,7-Pentahydroxyflavone 3-rutinosidePhytoBank
3,3’,4’,5,7-Pentahydroxyflavone 3-rutinosidePhytoBank
3-O-RutinosylquercetinPhytoBank
3-RutinosylquercetinPhytoBank
5,7,3',4'-Tetrahydroxyflavonol-3-O-rutinosidePhytoBank
5,7,3’,4’-Tetrahydroxyflavonol-3-O-rutinosidePhytoBank
IlixathinPhytoBank
MyrticalorinPhytoBank
MyticolorinPhytoBank
Quercetin 3-(6-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranoside)PhytoBank
Quercetin 3-(6-O-α-L-rhamnopyranosyl-β-D-glucopyranoside)PhytoBank
Quercetin 6-O-alpha-L-rhamnosyl-beta-D-glucosidePhytoBank
Quercetin 6-O-α-L-rhamnosyl-β-D-glucosidePhytoBank
Quercetin-3-O-[alpha-L-rhamnopyranosyl-(1->6)-beta-D-glucopyranoside]PhytoBank
Quercetin-3-O-[α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranoside]PhytoBank
Quercetin 3-O-alpha-L-rhamnopyranosyl-(1->6)-beta-D-glucopyranosidePhytoBank
Quercetin 3-O-α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranosidePhytoBank
Quercetin 3-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranosidePhytoBank
Quercetin 3-O-α-L-rhamnopyranosyl-β-D-glucopyranosidePhytoBank
Quercetin 3-O-alpha-rhamnopyranosyl(1''->6')-beta-D-glucopyranosidePhytoBank
Quercetin 3-O-α-rhamnopyranosyl(1''→6')-β-D-glucopyranosidePhytoBank
Quercetin 3-O-α-rhamnopyranosyl(1’’→6’)-β-D-glucopyranosidePhytoBank
Quercetin 3-O-alpha-rhamnopyranosyl(1->6)-beta-glucopyranosidePhytoBank
Quercetin 3-O-α-rhamnopyranosyl(1→6)-β-glucopyranosidePhytoBank
Quercetin 3-O-alpha-rhamnopyranosyl-(1'''->6'')-beta-glucopyranosidePhytoBank
Quercetin 3-O-α-rhamnopyranosyl-(1'''→6'')-β-glucopyranosidePhytoBank
Quercetin 3-O-α-rhamnopyranosyl-(1’’’→6’’)-β-glucopyranosidePhytoBank
Quercetin 3-O-beta-D-(6''-O-alpha-L-rhamnopyranosyl)glucopyranosidePhytoBank
Quercetin 3-O-β-D-(6''-O-α-L-rhamnopyranosyl)glucopyranosidePhytoBank
Quercetin 3-O-β-D-(6’’-O-α-L-rhamnopyranosyl)glucopyranosidePhytoBank
Quercetin 3-O-β-D-rutinosidePhytoBank
Quercetin 3-O-beta-rutinosidePhytoBank
Quercetin 3-O-β-rutinosidePhytoBank
Quercetin 3-beta-rutinosidePhytoBank
Quercetin 3-β-rutinosidePhytoBank
Quercetin-3-O-[alpha-L-rhamnopyranosyl-(1→6)-beta-D-glucopyranoside]PhytoBank
Quercetin 3-O-alpha-L-rhamnopyranosyl-(1→6)-beta-D-glucopyranosidePhytoBank
Quercetin 3-O-alpha-rhamnopyranosyl(1''→6')-beta-D-glucopyranosidePhytoBank
Quercetin 3-O-alpha-rhamnopyranosyl(1→6)-beta-glucopyranosidePhytoBank
Quercetin 3-O-alpha-rhamnopyranosyl-(1'''→6'')-beta-glucopyranosidePhytoBank
Quercetin rutinosidePhytoBank
RutozidPhytoBank
ViolaquercetrinPhytoBank
Chemical FormulaC27H30O16
Average Molecular Weight610.52
Monoisotopic Molecular Weight610.1534
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
Traditional Nametroxerutin
CAS Registry Number153-18-4
SMILES
C[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
InChI Identifier
InChI=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
Chemical Taxonomy
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
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point125 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.12 mg/mLNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSRutin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-052p-7581190000-d9593c696e6c6e2454edSpectrum
Predicted GC-MSRutin, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSRutin, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSRutin, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSRutin, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSRutin, TMS_1_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSRutin, TMS_1_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSRutin, TMS_1_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSRutin, TMS_1_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSRutin, TMS_1_9, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSRutin, TMS_1_10, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSRutin, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSRutin, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSRutin, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSRutin, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSRutin, TMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSRutin, TMS_2_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSRutin, TMS_2_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSRutin, TMS_2_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSRutin, TMS_2_9, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSRutin, TMS_2_10, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSRutin, TMS_2_11, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSRutin, TMS_2_12, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSRutin, TMS_2_13, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSRutin, TMS_2_14, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-0000009000-a6b8403579a83c69506b2012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-03di-0002009000-ffacf122369038644c022012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0w29-5009015000-f74826ba5205775d12b82012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 5V, Positivesplash10-03di-0003109000-85542c3510756d258e112012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Positivesplash10-0ik9-0008109000-f0d08078ad4b887cce0d2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Negativesplash10-0a4i-0000009000-f07697affe03ff93dad32012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Positivesplash10-0udi-0009000000-1b117e308c1ab00aa4a72012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0a4i-0000009000-270308e3f77a0404dea82017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0a4i-0010009000-f94b0edacf4c3bc9c9e32017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-0udi-0049001000-8327d9d15b0d22a0c9682017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0a4i-0000009000-270308e3f77a0404dea82017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0a4i-0010009000-f94b0edacf4c3bc9c9e32017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-0udi-0049001000-8327d9d15b0d22a0c9682017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0udi-0009100000-dfc0a2b72193a5072dde2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0a4i-0000009000-dd163a2a17fe559c34822017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0a4i-0000009000-7b408d31853f85c126192017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0a4i-0001009000-3a559cbd175dfd7bafc92017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0009005000-a090fd87b44b66b9f0c02017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0009000000-8454cc7afaccaa2be7ac2017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0139143000-0b231bbaf0f8cd578ce92017-07-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0249200000-5766b78c90749219634c2017-07-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udr-1955000000-49ac7b74c557179bbcae2017-07-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0pb9-5539337000-13a750c25d00b7185c082017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-3539010000-707593795636ef3841c12017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-3966000000-61676ecb8f5b5e5147602017-07-26View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 50.32 MHz, DMSO-d6, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Spectrum
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Aldo-keto reductase family 1 member C3AKR1C310p15-p14P42330 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Cytochrome P450 3A4CYP3A47q21.1P08684 details
Cytochrome P450 2C9CYP2C910q24P11712 details
Cytochrome P450 2D6CYP2D622q13.1P10635 details
Cytochrome P450 2C8CYP2C810q23.33P10632 details
Receptors
Protein NameGene NameLocusUniprot IDDetails
Aldo-keto reductase family 1 member C3AKR1C310p15-p14P42330 details
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0003249
DrugBank IDDB01698
Phenol Explorer Compound ID296
FoodDB IDFDB002536
KNApSAcK IDC00005413
Chemspider ID4444362
KEGG Compound IDC05625
BioCyc IDRUTIN
BiGG IDNot Available
Wikipedia LinkRutin
METLIN ID3677
PubChem Compound5280805
PDB IDNot Available
ChEBI ID28527
References
General ReferencesNot Available

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the conversion of aldehydes and ketones to alcohols. Catalyzes the reduction of prostaglandin (PG) D2, PGH2 and phenanthrenequinone (PQ) and the oxidation of 9-alpha,11-beta-PGF2 to PGD2. Functions as a bi-directional 3-alpha-, 17-beta- and 20-alpha HSD. Can interconvert active androgens, estrogens and progestins with their cognate inactive metabolites. Preferentially transforms androstenedione (4-dione) to testosterone.
Gene Name:
AKR1C3
Uniprot ID:
P42330
Molecular weight:
36866.91