You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 15:12:44 UTC
Update Date2018-05-20 20:42:15 UTC
HMDB IDHMDB0003249
Secondary Accession Numbers
  • HMDB03249
Metabolite Identification
Common NameRutin
DescriptionRutin is a flavonoid known to have a variety of biological activities including antiallergic, anti-inflammatory, antiproliferative, and anticarcinogenic properties. A large number of flavonoids, mostly O-glycosides, are polyphenolic compounds of natural origin that are present in most fruits and vegetables. The average intake of the compounds by humans on a normal diet is more than 1 g per day. Although flavonoids are devoid of classical nutritional value, they are increasingly viewed as beneficial dietary components that act as potential protectors against human diseases such as coronary heart disease, cancers, and inflammatory bowel disease. Rutin acts as a quercetin deliverer to the large intestine; moreover, quercetin is extensively metabolized in the large intestine, which suggests that quercetin liberated from rutin and/or its colonic metabolites may play a role. Rutin's anti-inflammatory actions are mediated through a molecular mechanism that underlies the quercetin-mediated therapeutic effects: quercetin-mediated inhibition of tumor necrosis factor-alpha (TNF-alpha)-induced nuclear factor kappa B (NFkB) activation. TNF-alpha-induced NFkB activity plays a central role in the production of pro-inflammatory mediators involved in progression of gut inflammation. (PMID: 16132362 , Pharm Res. 2005 Sep;22(9):1499-509. Epub 2005 Aug 24.).
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
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
VenorutonHMDB
ViolaquercitrinHMDB
Vitamin PHMDB
3-Rhamnosyl-glucosyl quercetinMeSH
Quercetin 3 rutinosideMeSH
Quercetin, 3-rhamnosyl-glucosylMeSH
Chemical FormulaC27H30O16
Average Molecular Weight610.5175
Monoisotopic Molecular Weight610.153384912
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
DescriptionThis compound 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
Water Solubility3.54 g/LALOGPS
logP0.15ALOGPS
logP-0.87ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)6.43ChemAxon
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
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
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.72-0.75 uMAdult (>18 years old)BothNormal details
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 296 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
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 IDRUT
ChEBI ID28527
References
Synthesis ReferenceWinderlich, A. Viola Rutin (Violaquercitrin). Arch. Pharm. (1909), 246 224-38. CAN 3:1624 AN 1909:1624
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Lindahl M, Tagesson C: Flavonoids as phospholipase A2 inhibitors: importance of their structure for selective inhibition of group II phospholipase A2. Inflammation. 1997 Jun;21(3):347-56. [PubMed:9246576 ]
  2. Olthof MR, Hollman PC, Buijsman MN, van Amelsvoort JM, Katan MB: Chlorogenic acid, quercetin-3-rutinoside and black tea phenols are extensively metabolized in humans. J Nutr. 2003 Jun;133(6):1806-14. [PubMed:12771321 ]
  3. Broks PD: Effect of o-(beta-hydroxyethyl)-rutoside in lymphangiography. AJR Am J Roentgenol. 1977 Feb;128(2):263-5. [PubMed:401613 ]
  4. Hackett AM, Griffiths LA, Luyckx AS, van Cauwenberge H: Metabolism of hydroxyethylrutosides (HR): metabolism of [14C]-HR in man. Arzneimittelforschung. 1976;26(5):925-8. [PubMed:989368 ]
  5. Nielsen SE, Freese R, Cornett C, Dragsted LO: Identification and quantification of flavonoids in human urine samples by column-switching liquid chromatography coupled to atmospheric pressure chemical ionization mass spectrometry. Anal Chem. 2000 Apr 1;72(7):1503-9. [PubMed:10763246 ]
  6. Bihari I, Meleg M: [Conservative management of lymphedema of the limbs]. Orv Hetil. 1991 Aug 4;132(31):1705-8. [PubMed:1866167 ]
  7. Gerdin B, Svensjo E: Inhibitory effect of the flavonoid O-(beta-hydroxyethyl)-rutoside on increased microvascular permeability induced by various agents in rat skin. Int J Microcirc Clin Exp. 1983;2(1):39-46. [PubMed:6088413 ]
  8. Kim H, Kong H, Choi B, Yang Y, Kim Y, Lim MJ, Neckers L, Jung Y: Metabolic and pharmacological properties of rutin, a dietary quercetin glycoside, for treatment of inflammatory bowel disease. Pharm Res. 2005 Sep;22(9):1499-509. Epub 2005 Aug 24. [PubMed:16132362 ]

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
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular weight:
55627.365
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular weight:
55768.94
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti-cancer drug paclitaxel (taxol).
Gene Name:
CYP2C8
Uniprot ID:
P10632
Molecular weight:
55824.275
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]