<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-19 02:25:36 UTC</creation_date>
  <update_date>2026-05-14 17:13:19 UTC</update_date>
  <accession/>
  <common_name>RUTIN</common_name>
  <class>SmallMolecule</class>
  <description>RUTIN belongs to the flavonoid glycosides, a subclass of flavonoids within the organic compounds. With an average molecular weight of 610.52 g/mol, RUTIN is a heavy molecule with the formula C27H30O16. Biologically, it functions as a ligand (PMC12540936), an antioxidant (PMC11478989, PMC11548494, PMC11643819, PMC13031289, PMC13470057), and an iron chelator (PMC13470057). In industrial applications, it is used as a stabilizer (PMC9918917) and as a nutrient and flavouring (PMC11478989, PMC11548494, PMC11643819, PMC13031289, PMC13470057). It is further classified biologically as part of the flavonoids (PMC11832627). The compound acts as an inhibitor of Carbonyl reductase [NADPH] 1 (CBR1) and Aldo-keto reductase family 1 member C3 (AKR1C3).

RUTIN is found in 36 recorded sources, including healthcare, pharmaceuticals &amp; veterinary products such as medical devices and vasoprotectives; electrical &amp; electronic equipment including batteries, cell phones, capacitors, printed circuit boards, and wires and cables; food, food processing &amp; cookware including the preparation of malt, molasses and treatment of molasses, cellar tools, food packaging, and agglomerated sugar products; building &amp; construction including fencing and ceilings; textiles, leather &amp; furnishings including carpets, rugs, and synthetic textiles; and household cleaning &amp; consumer products such as soap dispensers, other smoking requisites, tobacco product cases, and non electric simulated smoking devices. Exposure routes include oral, inhalation, and touch.

The compound exhibits therapeutic effects on inflammation (PMC11478989, PMC12968236, PMC13031289, PMC13470057, PMC3872418), hyperglycemia (PMC12968236, PMC9379957), proteinuria (PMC12968236), and type 2 diabetes mellitus (PMC11478989). It is associated with therapeutic effects on glioblastoma (PMC12466395), colon cancer (PMC6130576), diabetic neuropathy (PMC9423984), anxiety (PMC10831359), seizure (PMC10831359), necrosis (PMC13470057), hypertension (PMC13470057), Alzheimer's disease (PMC13470057), and Parkinson's disease (PMC13470057). Additionally, it is a treatment for hepatic steatosis (PMC13470057), hepatitis (PMC13470057), and hypertension (PMC13470057).</description>
  <categories/>
  <types>
    <type>PFAS</type>
    <type>Phytotoxin</type>
  </types>
  <synonyms>
    <synonym>Quercetin 3-rutinoside</synonym>
    <synonym>Rutin trihydrate</synonym>
    <synonym>Rutoside</synonym>
  </synonyms>
  <chemical_formula>C27H30O16</chemical_formula>
  <average_molecular_weight>610.5175</average_molecular_weight>
  <monisotopic_moleculate_weight>610.153384912</monisotopic_moleculate_weight>
  <iupac_name>2-(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</iupac_name>
  <traditional_iupac>troxerutin</traditional_iupac>
  <cas_registry_number>153-18-4</cas_registry_number>
  <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</smiles>
  <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</inchi>
  <inchikey>IKGXIBQEEMLURG-NVPNHPEKSA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Phenylpropanoids and polyketides</super_class>
    <class>Flavonoids</class>
    <sub_class>Flavonoid glycosides</sub_class>
    <direct_parent>Flavonoid-3-O-glycosides</direct_parent>
    <alternate_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>1-hydroxy-4-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>3'-hydroxyflavonoids</alternative_parent>
      <alternative_parent>4'-hydroxyflavonoids</alternative_parent>
      <alternative_parent>5-hydroxyflavonoids</alternative_parent>
      <alternative_parent>7-hydroxyflavonoids</alternative_parent>
      <alternative_parent>Acetals</alternative_parent>
      <alternative_parent>Benzene and substituted derivatives</alternative_parent>
      <alternative_parent>Catechols</alternative_parent>
      <alternative_parent>Chromones</alternative_parent>
      <alternative_parent>Disaccharides</alternative_parent>
      <alternative_parent>Flavones</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>O-glycosyl compounds</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Pyranones and derivatives</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Vinylogous acids</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>1-benzopyran</substituent>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>1-hydroxy-4-unsubstituted benzenoid</substituent>
      <substituent>3'-hydroxyflavonoid</substituent>
      <substituent>4'-hydroxyflavonoid</substituent>
      <substituent>5-hydroxyflavonoid</substituent>
      <substituent>7-hydroxyflavonoid</substituent>
      <substituent>Acetal</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Benzopyran</substituent>
      <substituent>Catechol</substituent>
      <substituent>Chromone</substituent>
      <substituent>Disaccharide</substituent>
      <substituent>Flavone</substituent>
      <substituent>Flavonoid-3-o-glycoside</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxyflavonoid</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>O-glycosyl compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Phenol</substituent>
      <substituent>Polyol</substituent>
      <substituent>Pyran</substituent>
      <substituent>Pyranone</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Vinylogous acid</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <descriptors>
      <descriptor>disaccharide derivative</descriptor>
      <descriptor>flavonols</descriptor>
      <descriptor>quercetin O-glucoside</descriptor>
      <descriptor>rutinoside</descriptor>
      <descriptor>tetrahydroxyflavone</descriptor>
    </descriptors>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways>
    <pathway>
      <name>Rutin Drug Metabolism Action Pathway</name>
      <smpdb_id>SMP0143827</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <state/>
  <appearance/>
  <experimental_properties>
    <property>
      <kind>logp</kind>
      <value>-0.87</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.15</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.24</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>3.54e+00 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.87</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>6.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-(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</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>610.5175</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>610.153384912</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>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</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C27H30O16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>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</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>IKGXIBQEEMLURG-NVPNHPEKSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>265.52</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>140.15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>57.08</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <route_of_exposure/>
  <mechanism_of_toxicity/>
  <metabolism/>
  <toxicity/>
  <lethaldose/>
  <carcinogenicity/>
  <use_source/>
  <min_risk_level/>
  <health_effects>#&lt;HealthEffect::ActiveRecord_Associations_CollectionProxy:0x00007f7277749398&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB01698</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>5280805</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id>4444362</chemspider_id>
  <kegg_id/>
  <uniprot_id/>
  <omim_id/>
  <chebi_id/>
  <biocyc_id/>
  <ctd_id/>
  <stitch_id/>
  <actor_id/>
  <pdb_id/>
  <wikipidia/>
  <general_references/>
  <targets>
    <target>
      <target_id/>
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    <target>
      <target_id>BE0000592</target_id>
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    <target>
      <target_id>BE0003074</target_id>
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  </targets>
</compound>
