<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">4104</id>
  <title>T3D4050</title>
  <common-name>alpha-Chaconine</common-name>
  <description>alpha-Chaconine is found in potato. alpha-Chaconine is an alkaloid from Solanum chacoense and very many other Solanum species (Solanaceae). Alpha-chaconine has been shown to exhibit anti-angiogenic and anti-fungal functions  (A3215, A3216).</description>
  <cas>20562-03-2</cas>
  <pubchem-id>4115417</pubchem-id>
  <chemical-formula>C45H73NO14</chemical-formula>
  <weight nil="true"/>
  <appearance>White powder.</appearance>
  <melting-point>243°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>Alpha-Chaconine has inhibitory effect on lung adenocarcinoma cell metastasis in vitro. Alpha-chaconine could inhibit phosphorylation of c-Jun N-terminal kinase (JNK) and Akt, whereas it did not affected phosphorylation of extracellular signal regulating kinase (ERK) and p38. In addition, alpha-chaconine significantly decreased the nuclear level of nuclear factor kappa B (NF-_B) and the binding ability of NF-_B. Therefore, alpha-chaconine inhibited A549 cell metastasis by a reduction of matrix metalloproteinase-2 (MMP-2) and matrix metalloproteinase-9 (MMP-9) activities involving suppression of phosphoinositide 3-kinase/Akt/NF-_B (PI3K/Akt/NF-_B) signaling pathway. Alpha-chaconine has exhibited its antiproliferative and apoptotic effects on the growth of cancer cells originating from human skin, liver, prostate, breast, and colon. In addition to the cytotoxicity in various cancer cells, R-chaconine induces significant cytotoxicity in Chang, normal human liver cells. (A15417)</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>alpha-Chaconine is found in potato.</use-source>
  <min-risk-level nil="true"/>
  <health-effects nil="true"/>
  <symptoms nil="true"/>
  <treatment nil="true"/>
  <created-at type="dateTime">2014-08-29T04:58:10Z</created-at>
  <updated-at type="dateTime">2026-04-06T01:49:50Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia nil="true"/>
  <uniprot-id nil="true"/>
  <kegg-compound-id>C10796</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>CC1C2CCC(C)CN2C2CC3C4CC=C5CC(CCC5(C)C4CCC3(C)C12)OC1OC(CO)C(OC2OC(C)C(O)C(O)C2O)C(O)C1OC1OC(C)C(O)C(O)C1O</moldb-smiles>
  <moldb-formula>C45H73NO14</moldb-formula>
  <moldb-inchi>InChI=1S/C45H73NO14/c1-19-7-10-28-20(2)31-29(46(28)17-19)16-27-25-9-8-23-15-24(11-13-44(23,5)26(25)12-14-45(27,31)6)57-43-40(60-42-37(53)35(51)33(49)22(4)56-42)38(54)39(30(18-47)58-43)59-41-36(52)34(50)32(48)21(3)55-41/h8,19-22,24-43,47-54H,7,9-18H2,1-6H3</moldb-inchi>
  <moldb-inchikey>TYNQWWGVEGFKRU-UHFFFAOYSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">852.0594</moldb-average-mass>
  <moldb-mono-mass type="decimal">851.503106049</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp nil="true"/>
  <hmdb-id>HMDB39353</hmdb-id>
  <chembl-id nil="true"/>
  <chemspider-id>3328941</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 nil="true"/>
  <structure-image-caption nil="true"/>
  <chemdb-id>CHEM003010</chemdb-id>
  <dsstox-id>DTXSID501016601</dsstox-id>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00094322</susdat-id>
  <iupac nil="true"/>
  <moldb-polar-surface-area>220.45999999999995</moldb-polar-surface-area>
  <moldb-refractivity>215.00990000000004</moldb-refractivity>
  <moldb-polarizability>96.30670834802265</moldb-polarizability>
  <moldb-rotatable-bond-count>7</moldb-rotatable-bond-count>
  <moldb-acceptor-count>15</moldb-acceptor-count>
  <moldb-donor-count>8</moldb-donor-count>
  <moldb-pka-strongest-acidic>12.218002600948315</moldb-pka-strongest-acidic>
  <moldb-pka-strongest-basic>11.784001120236216</moldb-pka-strongest-basic>
  <moldb-physiological-charge>1</moldb-physiological-charge>
  <moldb-number-of-rings>9</moldb-number-of-rings>
  <moldb-alogps-logp>1.87</moldb-alogps-logp>
  <moldb-alogps-logs>-3.47</moldb-alogps-logs>
  <moldb-alogps-solubility>2.90e-01 g/l</moldb-alogps-solubility>
</compound>
