You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NameRutin
Accession NumberDB01698  (EXPT02824)
Typesmall molecule
Groupsexperimental
Description

A flavonol glycoside found in many plants, including buckwheat; tobacco; forsythia; hydrangea; viola, etc. It has been used therapeutically to decrease capillary fragility. [PubChem]

Structure
Thumb
Synonyms
SynonymLanguageCode
2-(3,4-Dihydroxyphenyl)-5,7-Dihydroxy-4-Oxo-4h-Chromen-3-Yl 6-O-(6-Deoxy-Alpha-L-Mannopyranosyl)-Beta-D-GlucopyranosideNot AvailableNot Available
PhytomelinNot AvailableNot Available
quercetin-3-rutinosideNot AvailableNot Available
RutosideNot AvailableNot Available
sophorinNot AvailableNot Available
SaltsNot Available
Brand namesNot Available
Brand mixturesNot Available
CategoriesNot Available
CAS number153-18-4
WeightAverage: 610.5175
Monoisotopic: 610.153384912
Chemical FormulaC27H30O16
InChI KeyIKGXIBQEEMLURG-BKUODXTLSA-N
InChI
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
IUPAC Name
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-({[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-4H-chromen-4-one
SMILES
C[C@@H]1O[C@H](OC[C@@H]2O[C@H](OC3=C(OC4=CC(O)=CC(O)=C4C3=O)C3=CC=C(O)C(O)=C3)[C@@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@H](O)[C@H]1O
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassPhenylpropanoids and Polyketides
ClassFlavonoids
SubclassFlavonoid Glycosides
Direct parentFlavonoid O-Glycosides
Alternative parentsDihexoses; Flavonols; O-glycosyl Compounds; Chromones; Catechols; Alkyl Aryl Ethers; Pyranones and Derivatives; Oxanes; Secondary Alcohols; 1,2-Diols; Polyamines; Acetals; Enols
Substituentsflavonol; flavone; glycosyl compound; o-glycosyl compound; disaccharide; chromone; benzopyran; 1,2-diphenol; alkyl aryl ether; pyranone; phenol derivative; pyran; saccharide; benzene; oxane; 1,2-diol; secondary alcohol; polyol; enol; polyamine; acetal; ether; alcohol
Classification descriptionThis compound belongs to the flavonoid o-glycosides. These are compounds containing a carbohydrate moiety which is o-glycosidically linked to one of the flavonoid backbones (2-phenylchromen-4-one, 3-phenylchromen-4-one or 4-phenylcoumarin).
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.8041
Blood Brain Barrier - 0.8542
Caco-2 permeable - 0.9172
P-glycoprotein substrate Substrate 0.6901
P-glycoprotein inhibitor I Non-inhibitor 0.8759
P-glycoprotein inhibitor II Non-inhibitor 0.8546
Renal organic cation transporter Non-inhibitor 0.8977
CYP450 2C9 substrate Non-substrate 0.7639
CYP450 2D6 substrate Non-substrate 0.8962
CYP450 3A4 substrate Non-substrate 0.5374
CYP450 1A2 substrate Non-inhibitor 0.8673
CYP450 2C9 substrate Non-inhibitor 0.9071
CYP450 2D6 substrate Non-inhibitor 0.9545
CYP450 2C19 substrate Non-inhibitor 0.9025
CYP450 3A4 substrate Non-inhibitor 0.9249
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.6787
Ames test Non AMES toxic 0.5118
Carcinogenicity Non-carcinogens 0.9608
Biodegradation Not ready biodegradable 0.8339
Rat acute toxicity 2.4984 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9814
hERG inhibition (predictor II) Non-inhibitor 0.7469
Pharmacoeconomics
ManufacturersNot Available
Packagers
  • V Sab Medical Labs Inc.
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point125 °CPhysProp
water solubility125 mg/LMERCK (1989)
Predicted Properties
PropertyValueSource
water solubility3.54e+00 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 area265.52ChemAxon
rotatable bond count6ChemAxon
refractivity140.15ChemAxon
polarizability57.69ChemAxon
number of rings5ChemAxon
bioavailability0ChemAxon
rule of fiveNoChemAxon
Ghose filterNoChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleYesChemAxon
Spectra
SpectraNot Available
References
Synthesis Reference

Yukio Suzuki, Kei Suzuki, Masaru Yoneyama, Toshio Miyake, “4.sup.G -alpha-D-glucopyranosyl rutin, and its preparation and uses.” U.S. Patent US5171573, issued October, 1979.

US5171573
General ReferenceNot Available
External Links
ResourceLink
KEGG CompoundC05625
PubChem Compound46936193
PubChem Substance46508549
ChemSpider4454825
ChEBI28527
ChEMBL
PharmGKBPA451291
HETRUT
Drug Product Database141240
WikipediaRutin
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSshow(72 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Aldo-keto reductase family 1 member C3

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Aldo-keto reductase family 1 member C3 P42330 Details

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
  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

Enzymes

1. Cytochrome P450 2C8

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2C8 P10632 Details

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. Epub 2009 Nov 24. Pubmed

2. Cytochrome P450 2C9

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2C9 P11712 Details

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. Epub 2009 Nov 24. Pubmed

3. Cytochrome P450 2D6

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2D6 P10635 Details

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. Epub 2009 Nov 24. Pubmed

4. Cytochrome P450 3A4

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 3A4 P08684 Details

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. Epub 2009 Nov 24. Pubmed

Comments
comments powered by Disqus
Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:15