<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">4146</id>
  <title>T3D4092</title>
  <common-name>Dicentrine</common-name>
  <description>Dicentrine is an anticancer compound isolated from Lindera, a species of flowering plants.</description>
  <cas>517-66-8</cas>
  <pubchem-id>101300</pubchem-id>
  <chemical-formula>C20H21NO4</chemical-formula>
  <weight nil="true"/>
  <appearance>White powder.</appearance>
  <melting-point></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></route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>Dicentrine was found to be a potent alpha 1-adrenoceptor blocking agent in rat thoracic aorta as revealed by its competitive antagonism of noradrenaline- (pA2 = 8.19 +/- 0.09) or phenylephrine (pA2 = 9.01 +/- 0.10)-induced vasoconstriction. These effects still persisted in denuded aorta. Dicentrine inhibited platelet aggregation and release reaction through the suppression of thromboxane formation and elevation of adenosine 3': S'-cyclic monophosphate. (A15323) d-Dicentrine significantly inhibits the growth of human hepatoma cell line HuH-7 by delaying its doubling time in tissue culture. An in vitro colony forming assay showed that d-dicentrine decreased the colony formation efficiency in both hepatoma cell lines, HuH-7 and MS-G2. An MTT assay in 21 tumor cell lines also revealed that d-dicentrine was most cytotoxic to esophageal carcinoma HCE-6, lymphoma cell lines Molt-4 and CESS, leukemia cell lines HL60 and K562, and hepatoma cell line MS-G2. (A15341) Dicentrine is also a selective α1-adrenoceptor antagonist with potent antiarrhythmic and antihypertensive activities. (A15324)</mechanism-of-toxicity>
  <metabolism></metabolism>
  <toxicity></toxicity>
  <lethaldose></lethaldose>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>Dicentrine is an anticancer compound isolated from Lindera, a species of flowering plants.</use-source>
  <min-risk-level></min-risk-level>
  <health-effects></health-effects>
  <symptoms></symptoms>
  <treatment></treatment>
  <created-at type="dateTime">2014-08-29T05:07:05Z</created-at>
  <updated-at type="dateTime">2026-04-06T02:08:15Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia></wikipedia>
  <uniprot-id></uniprot-id>
  <kegg-compound-id>C17426</kegg-compound-id>
  <omim-id></omim-id>
  <chebi-id></chebi-id>
  <biocyc-id></biocyc-id>
  <ctd-id></ctd-id>
  <stitch-id></stitch-id>
  <drugbank-id></drugbank-id>
  <pdb-id></pdb-id>
  <actor-id></actor-id>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-smiles>[H][C@]12CC3=CC(OC)=C(OC)C=C3C3=C1C(CCN2C)=CC1=C3OCO1</moldb-smiles>
  <moldb-formula>C20H21NO4</moldb-formula>
  <moldb-inchi>InChI=1S/C20H21NO4/c1-21-5-4-11-7-17-20(25-10-24-17)19-13-9-16(23-3)15(22-2)8-12(13)6-14(21)18(11)19/h7-9,14H,4-6,10H2,1-3H3/t14-/m0/s1</moldb-inchi>
  <moldb-inchikey>YJWBWQWUHVXPNC-AWEZNQCLSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">339.385</moldb-average-mass>
  <moldb-mono-mass type="decimal">339.147058165</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp></logp>
  <hmdb-id></hmdb-id>
  <chembl-id>CHEMBL464748</chembl-id>
  <chemspider-id>91532</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>CHEM003052</chemdb-id>
  <dsstox-id>DTXSID10199651</dsstox-id>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00094624</susdat-id>
  <iupac nil="true"/>
  <moldb-polar-surface-area>40.160000000000004</moldb-polar-surface-area>
  <moldb-refractivity>94.71959999999999</moldb-refractivity>
  <moldb-polarizability>37.116456100708916</moldb-polarizability>
  <moldb-rotatable-bond-count>2</moldb-rotatable-bond-count>
  <moldb-acceptor-count>5</moldb-acceptor-count>
  <moldb-donor-count>0</moldb-donor-count>
  <moldb-pka-strongest-acidic nil="true"/>
  <moldb-pka-strongest-basic>7.062561297435805</moldb-pka-strongest-basic>
  <moldb-physiological-charge>1</moldb-physiological-charge>
  <moldb-number-of-rings>5</moldb-number-of-rings>
  <moldb-alogps-logp>2.76</moldb-alogps-logp>
  <moldb-alogps-logs>-3.63</moldb-alogps-logs>
  <moldb-alogps-solubility>8.05e-02 g/l</moldb-alogps-solubility>
</compound>
