<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">4117</id>
  <title>T3D4063</title>
  <common-name>Ranunculin</common-name>
  <description>Ranunculin is an instable glucoside found in plants of the buttercup family (Ranunculaceae). On maceration, for example when the plant is wounded, it is enzymatically broken down into glucose and the toxin protoanemonin.</description>
  <cas>644-69-9</cas>
  <pubchem-id>441581</pubchem-id>
  <chemical-formula>C11H16O8</chemical-formula>
  <weight nil="true"/>
  <appearance>White powder.</appearance>
  <melting-point>141-142°C</melting-point>
  <boiling-point></boiling-point>
  <density nil="true"/>
  <solubility></solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure nil="true"/>
  <target nil="true"/>
  <mechanism-of-toxicity>Ranunculin (RAN) inhibited the incorporation of 3H-labeled precursors into DNA and RNA of L1210 cells. RAN (15 mumol/L) markedly decreased DNA synthesis catalyzed by DNA polymerase I and promoted the generation of superoxide anions in DMSO/KO2 system. In the meantime, SOD and CAT were shown to partly revoke the inhibitory effects of RAN upon the incorporation of 3H-TdR into DNA. The cytotoxicity of RAN in vitro may be due to inhibition of DNA polymerase and increase of oxygen free radicals. (A15425)</mechanism-of-toxicity>
  <metabolism nil="true"/>
  <toxicity nil="true"/>
  <lethaldose nil="true"/>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>Ranunculin is an instable glucoside found in plants of the buttercup family (Ranunculaceae). On maceration, for example when the plant is wounded, it is enzymatically broken down into glucose and the toxin protoanemonin.</use-source>
  <min-risk-level nil="true"/>
  <health-effects nil="true"/>
  <symptoms nil="true"/>
  <treatment nil="true"/>
  <created-at type="dateTime">2014-08-29T05:00:33Z</created-at>
  <updated-at type="dateTime">2026-04-04T19:00:11Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>Ranunculin</wikipedia>
  <uniprot-id nil="true"/>
  <kegg-compound-id>C08512</kegg-compound-id>
  <omim-id nil="true"/>
  <chebi-id nil="true"/>
  <biocyc-id nil="true"/>
  <ctd-id nil="true"/>
  <stitch-id nil="true"/>
  <drugbank-id nil="true"/>
  <pdb-id nil="true"/>
  <actor-id nil="true"/>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-smiles>[H][C@]1(CO[C@]2([H])O[C@]([H])(CO)[C@@]([H])(O)[C@]([H])(O)[C@@]2([H])O)OC(=O)C=C1</moldb-smiles>
  <moldb-formula>C11H16O8</moldb-formula>
  <moldb-inchi>InChI=1S/C11H16O8/c12-3-6-8(14)9(15)10(16)11(19-6)17-4-5-1-2-7(13)18-5/h1-2,5-6,8-12,14-16H,3-4H2/t5-,6+,8+,9-,10+,11+/m0/s1</moldb-inchi>
  <moldb-inchikey>TYWXNGXVSZRXNA-NVZSGMJQSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">276.2399</moldb-average-mass>
  <moldb-mono-mass type="decimal">276.084517488</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp nil="true"/>
  <hmdb-id nil="true"/>
  <chembl-id nil="true"/>
  <chemspider-id>390250</chemspider-id>
  <structure-image-file-name nil="true"/>
  <structure-image-content-type nil="true"/>
  <structure-image-file-size type="integer" nil="true"/>
  <structure-image-updated-at type="dateTime" nil="true"/>
  <biodb-id nil="true"/>
  <synthesis-reference></synthesis-reference>
  <structure-image-caption nil="true"/>
  <chemdb-id>CHEM003023</chemdb-id>
  <dsstox-id>DTXSID40982977</dsstox-id>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id nil="true"/>
  <iupac>(5S)-5-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-2,5-dihydrofuran-2-one</iupac>
</compound>
