<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">4289</id>
  <title>T3D4235</title>
  <common-name>Aplysiatoxin</common-name>
  <description>Aplysiatoxin is a cyanotoxin produced by certain cyanobacteria species. It is used as a defensive secretion to protect these cyanobacteria from predation by fish, being a potent irritant and carcinogen, by acting as a powerful activator of Protein kinase C. It has dermatotoxic activity causing inflamation of the skin. They are also potent tumour promoters.</description>
  <cas>52659-57-1</cas>
  <pubchem-id>21672114</pubchem-id>
  <chemical-formula>C32H47BrO10</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>Dermal; ingestion.</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>Aplysiatoxin is a 12-O-tetradecanoylphorbol-13-acetate (TPA)-type tumor promoter that activates protein kinase C (PKC) (A15358). In cancer cells, PKC isozymes are involved in cell proliferation, survival, invasion, migration, apoptosis, angiogenesis, and anticancer drug resistance through their increased or decreased participation in various cellular signaling pathways (L2138).</mechanism-of-toxicity>
  <metabolism></metabolism>
  <toxicity></toxicity>
  <lethaldose></lethaldose>
  <carcinogenicity>Not listed by IARC.</carcinogenicity>
  <use-source>Aplysiatoxin is a cyanotoxin produced by certain cyanobacteria species. It is used as a defensive secretion to protect these cyanobacteria from predation by fish, being a potent irritant and carcinogen, by acting as a powerful activator of Protein kinase C. It has dermatotoxic activity causing inflamation of the skin.</use-source>
  <min-risk-level></min-risk-level>
  <health-effects>Aplysiatoxin is one of the causative agents of 'swimmer’s itch'. It also has tumor-promoting effects. Aplysiatoxin and debromoaplysiatoxin were found to be the causative agents of a red alga Gracilaria coronopifolia poisoning in Hawaii (A15448).</health-effects>
  <symptoms>Inflammation of the skin. Vomiting, diarrhea and burning sensation of the mouth and throat (A15448).</symptoms>
  <treatment></treatment>
  <created-at type="dateTime">2014-08-29T05:57:31Z</created-at>
  <updated-at type="dateTime">2026-04-05T15:32:55Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>Aplysiatoxin</wikipedia>
  <uniprot-id></uniprot-id>
  <kegg-compound-id>C16769</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@](C)(O)[C@@]1([H])CC(=O)O[C@@]2([H])C[C@]3(O[C@]([H])([C@@]([H])(C)CC[C@]([H])(OC)C4=C(Br)C=CC(O)=C4)[C@@]2([H])C)O[C@@](O)(CC(=O)O1)[C@]([H])(C)CC3(C)C</moldb-smiles>
  <moldb-formula>C32H47BrO10</moldb-formula>
  <moldb-inchi>InChI=1S/C32H47BrO10/c1-17(8-11-24(39-7)22-12-21(35)9-10-23(22)33)29-19(3)26-15-32(42-29)30(5,6)14-18(2)31(38,43-32)16-28(37)40-25(20(4)34)13-27(36)41-26/h9-10,12,17-20,24-26,29,34-35,38H,8,11,13-16H2,1-7H3/t17-,18+,19-,20+,24-,25+,26-,29+,31-,32-/m0/s1</moldb-inchi>
  <moldb-inchikey>RHJPBGWFGOAEID-BEDNPZBZSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">671.614</moldb-average-mass>
  <moldb-mono-mass type="decimal">670.235260371</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp></logp>
  <hmdb-id></hmdb-id>
  <chembl-id>CHEMBL1256416</chembl-id>
  <chemspider-id>10282349</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>CHEM003195</chemdb-id>
  <dsstox-id>DTXSID60880082</dsstox-id>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00075604</susdat-id>
  <iupac nil="true"/>
  <moldb-polar-surface-area>140.98</moldb-polar-surface-area>
  <moldb-refractivity>159.71330000000006</moldb-refractivity>
  <moldb-polarizability>66.28279848842382</moldb-polarizability>
  <moldb-rotatable-bond-count>7</moldb-rotatable-bond-count>
  <moldb-acceptor-count>8</moldb-acceptor-count>
  <moldb-donor-count>3</moldb-donor-count>
  <moldb-pka-strongest-acidic>8.917008091749306</moldb-pka-strongest-acidic>
  <moldb-pka-strongest-basic>-3.0342786881768538</moldb-pka-strongest-basic>
  <moldb-physiological-charge>0</moldb-physiological-charge>
  <moldb-number-of-rings>4</moldb-number-of-rings>
  <moldb-alogps-logp>4.22</moldb-alogps-logp>
  <moldb-alogps-logs>-4.99</moldb-alogps-logs>
  <moldb-alogps-solubility>6.86e-03 g/l</moldb-alogps-solubility>
</compound>
