<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-22 04:27:57 UTC</creation_date>
  <update_date>2026-05-14 19:30:25 UTC</update_date>
  <accession/>
  <common_name>Artemisinin</common_name>
  <class>SmallMolecule</class>
  <description>Artemisinin (C15H22O5) is a compound with an average molecular weight of 282.34 g/mol. Artemisinin belongs to the terpene lactones, a subclass of prenol lipids within the organic compounds. Biologically, it functions as a drug (PMC9495708), an antioxidant (PMC9495708), and an antimalarial (PMC3768262, PMC4344607). Industrially, it is used as a biocide and as a softener and conditioner. It acts as an inhibitor of the mitochondrial protein target Dihydroorotate dehydrogenase (quinone).

The compound is used in the treatment of malaria (PMC11832355, PMC7793148, PMC9495708), cancer (PMC10059971), and fever (PMC7833388). Additionally, it has a therapeutic effect on polycystic ovary syndrome (PMC12947462). Artemisinin is found in or released from 22 recorded sources across several sectors. These include healthcare, pharmaceuticals &amp; veterinary products via medical devices; drinking water &amp; water supply via drinking water; textiles, leather &amp; furnishings such as carpets, rugs, and synthetic textiles; household cleaning &amp; consumer products including pipe accessories, tobacco pipes, and cigar cigarettes; food, food processing &amp; cookware including food packaging and the preparation of vinegar, wort, and fermentation processes for beer; and electrical &amp; electronic equipment such as batteries, capacitors, printed circuit boards, wires, cables, and cell phones, among three more sectors. Recorded routes of exposure include oral, inhalation, and touch.</description>
  <categories/>
  <types>
    <type>Human Neurotoxin</type>
    <type>PFAS</type>
    <type>Phytotoxin</type>
  </types>
  <synonyms>
    <synonym>(3R,5aS,6R,8aS,9R,12S,12aR)-3,6,9-trimethyloctahydro-3,12-epoxypyrano[4,3-j][1,2]benzodioxepin-10(3H)-one</synonym>
  </synonyms>
  <chemical_formula>C15H22O5</chemical_formula>
  <average_molecular_weight>282.336</average_molecular_weight>
  <monisotopic_moleculate_weight>282.146723808</monisotopic_moleculate_weight>
  <iupac_name>(1R,4S,5R,8S,9R,12S,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0⁴,¹³.0⁸,¹³]hexadecan-10-one</iupac_name>
  <traditional_iupac>(+)-artemisinin</traditional_iupac>
  <cas_registry_number>63968-64-9</cas_registry_number>
  <smiles>[H][C@@]1(C)CC[C@@]2([H])[C@@]([H])(C)C(=O)O[C@]3([H])O[C@@]4(C)CC[C@]1([H])[C@@]23OO4</smiles>
  <inchi>InChI=1S/C15H22O5/c1-8-4-5-11-9(2)12(16)17-13-15(11)10(8)6-7-14(3,18-13)19-20-15/h8-11,13H,4-7H2,1-3H3/t8-,9-,10+,11+,13-,14-,15-/m1/s1</inchi>
  <inchikey>BLUAFEHZUWYNDE-NNWCWBAJSA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Prenol lipids</class>
    <sub_class>Terpene lactones</sub_class>
    <direct_parent>Terpene lactones</direct_parent>
    <alternate_parents>
      <alternative_parent>Acetals</alternative_parent>
      <alternative_parent>Artemisinins</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acid esters</alternative_parent>
      <alternative_parent>Delta valerolactones</alternative_parent>
      <alternative_parent>Dialkyl peroxides</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Oxepanes</alternative_parent>
      <alternative_parent>Trioxanes</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>1,2,4-trioxane</substituent>
      <substituent>Acetal</substituent>
      <substituent>Aliphatic heteropolycyclic compound</substituent>
      <substituent>Artemisinin skeleton</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid ester</substituent>
      <substituent>Delta valerolactone</substituent>
      <substituent>Delta_valerolactone</substituent>
      <substituent>Dialkyl peroxide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Lactone</substituent>
      <substituent>Monocarboxylic acid or derivatives</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>Oxepane</substituent>
      <substituent>Sesquiterpenoid</substituent>
      <substituent>Terpene lactone</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteropolycyclic compounds</molecular_framework>
    <descriptors>
      <descriptor>Eudesmane sesquiterpenoids</descriptor>
      <descriptor>Eudesmane sesquiterpenoids</descriptor>
      <descriptor>Sesquiterpenoids (C15)</descriptor>
      <descriptor>organic peroxide</descriptor>
      <descriptor>sesquiterpene lactone</descriptor>
    </descriptors>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways/>
  <state/>
  <appearance/>
  <experimental_properties>
    <property>
      <kind>logp</kind>
      <value>3.11</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.52</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.35</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>1.27e+00 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-4.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1R,4S,5R,8S,9R,12S,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0⁴,¹³.0⁸,¹³]hexadecan-10-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>282.336</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>282.146723808</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]1(C)CC[C@@]2([H])[C@@]([H])(C)C(=O)O[C@]3([H])O[C@@]4(C)CC[C@]1([H])[C@@]23OO4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C15H22O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C15H22O5/c1-8-4-5-11-9(2)12(16)17-13-15(11)10(8)6-7-14(3,18-13)19-20-15/h8-11,13H,4-7H2,1-3H3/t8-,9-,10+,11+,13-,14-,15-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>BLUAFEHZUWYNDE-NNWCWBAJSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>53.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>68.68</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>29.43</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</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>
  </predicted_properties>
  <route_of_exposure/>
  <mechanism_of_toxicity/>
  <metabolism/>
  <toxicity/>
  <lethaldose/>
  <carcinogenicity/>
  <use_source/>
  <min_risk_level/>
  <health_effects>#&lt;HealthEffect::ActiveRecord_Associations_CollectionProxy:0x00007f72267e7800&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB13132</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>68827</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id>62060</chemspider_id>
  <kegg_id/>
  <uniprot_id/>
  <omim_id/>
  <chebi_id/>
  <biocyc_id/>
  <ctd_id/>
  <stitch_id/>
  <actor_id/>
  <pdb_id/>
  <wikipidia/>
  <general_references/>
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</compound>
