<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:05:31 UTC</creation_date>
  <update_date>2025-11-18 22:40:35 UTC</update_date>
  <accession>FDB002776</accession>
  <name>Aesculin</name>
  <description>Vitamin C2 is generally considered a bioflavanoid, related to vitamin P

Aesculin is a glucoside that naturally occurs in the horse chestnut (Aesculus hippocastanum), California Buckeye (Aesculus californica) and in daphnin (the dark green resin of Daphne mezereum). Aesculin is found in many foods, some of which are barley, mugwort, chicory, and lentils.</description>
  <synonyms>
    <synonym>6,7-Dihydroxycoumarin 6-glucoside</synonym>
    <synonym>Aesculin</synonym>
    <synonym>Bicolorin</synonym>
    <synonym>Crataegin</synonym>
    <synonym>Enallachrome</synonym>
    <synonym>Escosyl</synonym>
    <synonym>Esculetin 6-&amp;beta;-D-glucoside</synonym>
    <synonym>Esculetin 6-b-D-glucoside</synonym>
    <synonym>Esculetin 6-beta-D-glucoside</synonym>
    <synonym>Esculetin 6-O-glucoside</synonym>
    <synonym>Esculin</synonym>
    <synonym>Esculine</synonym>
    <synonym>Esculoside</synonym>
    <synonym>Polychrom</synonym>
    <synonym>Polychrome</synonym>
    <synonym>Vitamin C2</synonym>
  </synonyms>
  <chemical_formula>C15H16O9</chemical_formula>
  <average_molecular_weight>340.2821</average_molecular_weight>
  <monisotopic_moleculate_weight>340.07943211</monisotopic_moleculate_weight>
  <iupac_name>7-hydroxy-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2H-chromen-2-one</iupac_name>
  <traditional_iupac>esculin</traditional_iupac>
  <cas_registry_number>531-75-9</cas_registry_number>
  <smiles>OCC1OC(OC2=C(O)C=C3OC(=O)C=CC3=C2)C(O)C(O)C1O</smiles>
  <inchi>InChI=1S/C15H16O9/c16-5-10-12(19)13(20)14(21)15(24-10)23-9-3-6-1-2-11(18)22-8(6)4-7(9)17/h1-4,10,12-17,19-21H,5H2</inchi>
  <inchikey>XHCADAYNFIFUHF-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as coumarin glycosides. These are aromatic compounds containing a carbohydrate moiety glycosidically bound to a coumarin moiety.</description>
    <direct_parent>Coumarin glycosides</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Phenylpropanoids and polyketides</super_class>
    <class>Coumarins and derivatives</class>
    <sub_class>Coumarin glycosides</sub_class>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>1-benzopyrans</alternative_parent>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>7-hydroxycoumarins</alternative_parent>
      <alternative_parent>Acetals</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hexoses</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Lactones</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>Phenolic glycosides</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Pyranones and derivatives</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-benzopyran</substituent>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>7-hydroxycoumarin</substituent>
      <substituent>Acetal</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Benzopyran</substituent>
      <substituent>Coumarin o-glycoside</substituent>
      <substituent>Coumarin-6-o-glycoside</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hexose monosaccharide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxycoumarin</substituent>
      <substituent>Lactone</substituent>
      <substituent>Monosaccharide</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>Phenolic glycoside</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Pyran</substituent>
      <substituent>Pyranone</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <external_descriptors>
      <external_descriptor>a small molecule</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <state/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.53</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.52</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>1.03e+01 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>Mp 205°</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>-1.1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>8.12</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>7-hydroxy-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2H-chromen-2-one</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>340.2821</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>340.07943211</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>OCC1OC(OC2=C(O)C=C3OC(=O)C=CC3=C2)C(O)C(O)C1O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C15H16O9</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C15H16O9/c16-5-10-12(19)13(20)14(21)15(24-10)23-9-3-6-1-2-11(18)22-8(6)4-7(9)17/h1-4,10,12-17,19-21H,5H2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>XHCADAYNFIFUHF-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>145.91</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>77.65</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>31.59</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>8</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>donor_count</kind>
    <value>5</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>physiological_charge</kind>
    <value>0</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formal_charge</kind>
    <value>0</value>
    <source>ChemAxon</source>
  </property>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>10753</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>42188</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>11000</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>11001</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>11002</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>17672</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>17673</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>17674</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439429</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439430</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439431</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447314</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449456</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449461</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB30820</hmdb_id>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id/>
  <biocyc_id/>
  <het_id/>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
    <reference>#&lt;Reference:0x000055ce3256c0b0&gt;</reference>
  </general_references>
  <foods>
    <food>
      <name>Barley</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Hordeum vulgare</name_scientific>
      <ncbi_taxonomy_id>4513</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Beer</name>
      <food_type>Type 2</food_type>
      <category>specific</category>
      <name_scientific/>
      <ncbi_taxonomy_id/>
      <average_value>0.01625</average_value>
      <max_value>0.016250001</max_value>
      <min_value>0.016250001</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Chicory</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Cichorium intybus</name_scientific>
      <ncbi_taxonomy_id>13427</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Common bean</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Phaseolus vulgaris</name_scientific>
      <ncbi_taxonomy_id>3885</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Grape wine</name>
      <food_type>Type 2</food_type>
      <category>specific</category>
      <name_scientific/>
      <ncbi_taxonomy_id/>
      <average_value>0.0</average_value>
      <max_value>0.0</max_value>
      <min_value>0.0</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Lentils</name>
      <food_type>Type 1</food_type>
      <category>generic</category>
      <name_scientific>Lens culinaris</name_scientific>
      <ncbi_taxonomy_id>3864</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Mugwort</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Artemisia vulgaris</name_scientific>
      <ncbi_taxonomy_id>4220</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Olive</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Olea europaea</name_scientific>
      <ncbi_taxonomy_id>4146</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Sweet basil</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Ocimum basilicum</name_scientific>
      <ncbi_taxonomy_id>39350</ncbi_taxonomy_id>
    </food>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
    <health_effect>
      <name>Aldose reductase inhibitor</name>
      <id>40</id>
      <definition>An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21).</definition>
    </health_effect>
    <health_effect>
      <name>Analgesic</name>
      <id>56</id>
      <definition>An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.</definition>
    </health_effect>
    <health_effect>
      <name>Anti acrocyanotic</name>
      <id>79</id>
      <definition>Any substance introduced into a living organism with therapeutic or diagnostic purpose.</definition>
    </health_effect>
    <health_effect>
      <name>Anti capillary-fragility</name>
      <id>160</id>
      <definition/>
    </health_effect>
    <health_effect>
      <name>Anti cellulitic</name>
      <id>170</id>
      <definition>Any substance introduced into a living organism with therapeutic or diagnostic purpose.</definition>
    </health_effect>
    <health_effect>
      <name>Anti CVS</name>
      <id>214</id>
      <definition/>
    </health_effect>
    <health_effect>
      <name>Anti dermatitic</name>
      <id>225</id>
      <definition>A drug used to treat or prevent skin disorders or for the routine care of skin.</definition>
    </health_effect>
    <health_effect>
      <name>Anti erythemic</name>
      <id>268</id>
      <definition>A drug used to treat or prevent skin disorders or for the routine care of skin.</definition>
    </health_effect>
    <health_effect>
      <name>Anti histaminic</name>
      <id>331</id>
      <definition>Histamine antagonists are the drugs that bind to but do not activate histamine receptors, thereby blocking the actions of histamine or histamine agonists.</definition>
    </health_effect>
    <health_effect>
      <name>Anti pyretic</name>
      <id>567</id>
      <definition>A drug that prevents or reduces fever by lowering the body temperature from a raised state. An antipyretic will not affect the normal body temperature if one does not have fever. Antipyretics cause the hypothalamus to override an interleukin-induced increase in temperature. The body will then work to lower the temperature and the result is a reduction in fever.</definition>
    </health_effect>
    <health_effect>
      <name>Anti Raynaud's</name>
      <id>573</id>
      <definition>Any substance introduced into a living organism with therapeutic or diagnostic purpose.</definition>
    </health_effect>
    <health_effect>
      <name>Anti-aging</name>
      <id>95</id>
      <definition>Any substance introduced into a living organism with therapeutic or diagnostic purpose.</definition>
    </health_effect>
    <health_effect>
      <name>Anti-alopecic</name>
      <id>104</id>
      <definition>Any substance introduced into a living organism with therapeutic or diagnostic purpose.</definition>
    </health_effect>
    <health_effect>
      <name>Anti-arthritic</name>
      <id>131</id>
      <definition>Any substance introduced into a living organism with therapeutic or diagnostic purpose.</definition>
    </health_effect>
    <health_effect>
      <name>Anti-hemorrhoidal</name>
      <id>322</id>
      <definition>Any substance introduced into a living organism with therapeutic or diagnostic purpose.</definition>
    </health_effect>
    <health_effect>
      <name>Anti-inflammatory</name>
      <id>370</id>
      <definition>A substance that reduces or suppresses inflammation.</definition>
    </health_effect>
    <health_effect>
      <name>Anti-oxidant</name>
      <id>502</id>
      <definition>A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.</definition>
    </health_effect>
    <health_effect>
      <name>Anti-panniculopathic</name>
      <id>506</id>
      <definition/>
    </health_effect>
    <health_effect>
      <name>Anti-seborrheic</name>
      <id>600</id>
      <definition>Any substance introduced into a living organism with therapeutic or diagnostic purpose.</definition>
    </health_effect>
    <health_effect>
      <name>Bacteristat</name>
      <id>725</id>
      <definition>A substance that kills or slows the growth of bacteria.</definition>
    </health_effect>
    <health_effect>
      <name>Cancer preventive</name>
      <id>754</id>
      <definition>A substance that inhibits or prevents the proliferation of neoplasms.</definition>
    </health_effect>
    <health_effect>
      <name>Cardiotonic</name>
      <id>771</id>
      <definition>A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.</definition>
    </health_effect>
    <health_effect>
      <name>Choleretic</name>
      <id>801</id>
      <definition/>
    </health_effect>
    <health_effect>
      <name>Cosmetic</name>
      <id>838</id>
      <definition>The role played by a substance in enhancing the appearance or odour of the human body; a name given to the substance itself or to a component of it.</definition>
    </health_effect>
    <health_effect>
      <name>Diuretic</name>
      <id>883</id>
      <definition>An agent that promotes the excretion of urine through its effects on kidney function.</definition>
    </health_effect>
    <health_effect>
      <name>Hypertensive</name>
      <id>1007</id>
      <definition/>
    </health_effect>
    <health_effect>
      <name>Lipoxygenase inhibitor</name>
      <id>1077</id>
      <definition>A compound or agent that combines with lipoxygenase and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of the icosanoid products hydroxyicosatetraenoic acid and various leukotrienes.</definition>
    </health_effect>
    <health_effect>
      <name>Microvasculokinetic</name>
      <id>1104</id>
      <definition/>
    </health_effect>
    <health_effect>
      <name>Paralytic</name>
      <id>1196</id>
      <definition/>
    </health_effect>
    <health_effect>
      <name>Sunscreen</name>
      <id>1337</id>
      <definition>Any substance introduced into a living organism with therapeutic or diagnostic purpose.</definition>
    </health_effect>
    <health_effect>
      <name>Toxic</name>
      <id>1371</id>
      <definition>A role played by the molecular entity or part thereof which causes the development of a pathological process.</definition>
    </health_effect>
    <health_effect>
      <name>Vasoprotective</name>
      <id>1416</id>
      <definition/>
    </health_effect>
  </health_effects>
</compound>
