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Identification
NameRutin
Accession NumberDB01698  (EXPT02824)
TypeSmall Molecule
GroupsExperimental
DescriptionA 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
2-(3,4-Dihydroxyphenyl)-5,7-Dihydroxy-4-Oxo-4h-Chromen-3-Yl 6-O-(6-Deoxy-Alpha-L-Mannopyranosyl)-Beta-D-Glucopyranoside
Phytomelin
quercetin-3-rutinoside
rutoside
sophorin
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNII5G06TVY3R7
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[[email protected]](OC[C@@H]2O[[email protected]](OC3=C(OC4=CC(O)=CC(O)=C4C3=O)C3=CC=C(O)C(O)=C3)[C@@H](O)[[email protected]](O)[[email protected]]2O)[C@@H](O)[[email protected]](O)[[email protected]]1O
Pharmacology
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action
TargetKindPharmacological actionActionsOrganismUniProt ID
Aldo-keto reductase family 1 member C3ProteinunknownNot AvailableHumanP42330 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
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
Interactions
Drug Interactions
DrugInteractionDrug group
AmodiaquineThe serum concentration of Amodiaquine can be increased when it is combined with Rutin.Approved
FesoterodineThe serum concentration of the active metabolites of Fesoterodine can be increased when Fesoterodine is used in combination with Rutin.Approved
MetoprololThe serum concentration of Metoprolol can be increased when it is combined with Rutin.Approved, Investigational
ThioridazineThe serum concentration of Thioridazine can be increased when it is combined with Rutin.Approved
Food InteractionsNot 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 ReferencesNot Available
External Links
ATC CodesC05CA01C05CA51
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSDownload (72 KB)
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.8041
Blood Brain Barrier-0.8542
Caco-2 permeable-0.9172
P-glycoprotein substrateSubstrate0.6901
P-glycoprotein inhibitor INon-inhibitor0.8759
P-glycoprotein inhibitor IINon-inhibitor0.8546
Renal organic cation transporterNon-inhibitor0.8977
CYP450 2C9 substrateNon-substrate0.7639
CYP450 2D6 substrateNon-substrate0.8962
CYP450 3A4 substrateNon-substrate0.5374
CYP450 1A2 substrateNon-inhibitor0.8673
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9545
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.9249
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6787
Ames testNon AMES toxic0.5118
CarcinogenicityNon-carcinogens0.9608
BiodegradationNot ready biodegradable0.8339
Rat acute toxicity2.4984 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9814
hERG inhibition (predictor II)Non-inhibitor0.7469
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
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 Solubility3.54 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity140.15 m3·mol-1ChemAxon
Polarizability57.69 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
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
  • 7-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 3'-hydroxyflavonoid
  • O-glycosyl compound
  • Glycosyl compound
  • Disaccharide
  • Chromone
  • 1-benzopyran
  • Benzopyran
  • Resorcinol
  • 1,2-diphenol
  • Pyranone
  • Phenol
  • Benzenoid
  • Pyran
  • Oxane
  • Saccharide
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Vinylogous acid
  • Secondary alcohol
  • Polyol
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Acetal
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase 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 andro...
Gene Name:
AKR1C3
Uniprot ID:
P42330
Molecular Weight:
36852.89 Da
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 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Steroid hydroxylase 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...
Gene Name:
CYP2C8
Uniprot ID:
P10632
Molecular Weight:
55824.275 Da
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 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Steroid hydroxylase 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, phenyto...
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular Weight:
55627.365 Da
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 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Steroid hydroxylase 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 Da
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 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Vitamin d3 25-hydroxylase 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 xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
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 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23