<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">4184</id>
  <title>T3D4130</title>
  <common-name>Gambieric acid B</common-name>
  <description>Gambieric acid B is an antifungal compound isolated from the marine dinoflagellate Gambierdiscus toxicus that produces ciguatoxin precursors and maitotoxin. The skeletal structure of gambieric acids (GAs) consists of a nonacrylic polyether core involuving six-, seven-, and nine- membered cyclic ethers, arranged with an isolated tetrahydrofuran ring (A-ring). GAs share the structural characteristics common to those of polycyclic ether neurotoxins, which are produced by G. toxicus, for example, ciguatoxin, maitotoxin, and gambierol  (A3251).</description>
  <cas>141363-65-7</cas>
  <pubchem-id>46173843</pubchem-id>
  <chemical-formula>C60H94O16</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 nil="true"/>
  <target nil="true"/>
  <mechanism-of-toxicity nil="true"/>
  <metabolism nil="true"/>
  <toxicity nil="true"/>
  <lethaldose nil="true"/>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>Gambieric acid B is an antifungal compound isolated from the marine dinoflagellate Gambierdiscus toxicus that produces ciguatoxin precursors and maitotoxin. The skeletal structure of gambieric acids (GAs) consists of a nonacrylic polyether core involuving six-, seven-, and nine- membered cyclic ethers, arranged with an isolated tetrahydrofuran ring (A-ring). GAs share the structural characteristics common to those of polycyclic ether neurotoxins, which are produced by G. toxicus, for example, ciguatoxin, maitotoxin, and gambierol  (A3251).</use-source>
  <min-risk-level nil="true"/>
  <health-effects nil="true"/>
  <symptoms nil="true"/>
  <treatment nil="true"/>
  <created-at type="dateTime">2014-08-29T05:25:15Z</created-at>
  <updated-at type="dateTime">2026-05-21T00:19:44Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia nil="true"/>
  <uniprot-id nil="true"/>
  <kegg-compound-id>C16886</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(=C(C)C[C@]1([H])O[C@]2(C)C[C@]3([H])O[C@]4([H])C[C@]5([H])O[C@]6([H])CC[C@]7([H])O[C@]8([H])C[C@]9([H])O[C@]([H])(C[C@]([H])(O)C[C@]%10([H])C[C@@]([H])(C)[C@]([H])(O%10)[C@@]([H])(C)CC(O)=O)[C@@](C)(O)CC[C@@]9([H])O[C@@]8(C)C[C@@]7(C)O[C@@]6([H])C\C([H])=C([H])/[C@@]([H])(C)[C@@]5([H])O[C@@]4(C)[C@]([H])(O)[C@@]3([H])O[C@@]2([H])CC1=C)[C@@]([H])(C)CO</moldb-smiles>
  <moldb-formula>C60H94O16</moldb-formula>
  <moldb-inchi>InChI=1S/C60H94O16/c1-31(19-32(2)29-61)20-42-34(4)22-48-57(8,75-42)28-45-54(72-48)55(65)60(11)50(70-45)27-44-53(76-60)33(3)13-12-14-40-39(68-44)15-16-46-58(9,73-40)30-59(10)49(71-46)26-43-41(74-59)17-18-56(7,66)47(69-43)25-37(62)24-38-21-35(5)52(67-38)36(6)23-51(63)64/h12-13,19,32-33,35-50,52-55,61-62,65-66H,4,14-18,20-30H2,1-3,5-11H3,(H,63,64)/b13-12-,31-19+/t32-,33-,35-,36+,37-,38+,39-,40+,41-,42+,43+,44+,45+,46+,47-,48+,49-,50-,52+,53-,54+,55-,56+,57-,58-,59+,60-/m1/s1</moldb-inchi>
  <moldb-inchikey>PLNXKBYHTXJJIY-ISIUNFMJSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">1071.3788</moldb-average-mass>
  <moldb-mono-mass type="decimal">1070.65418696</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp nil="true"/>
  <hmdb-id nil="true"/>
  <chembl-id nil="true"/>
  <chemspider-id>28285403</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>CHEM003090</chemdb-id>
  <dsstox-id>DTXSID20880109</dsstox-id>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00075596</susdat-id>
  <iupac nil="true"/>
  <moldb-polar-surface-area>210.51999999999992</moldb-polar-surface-area>
  <moldb-refractivity>282.25789999999984</moldb-refractivity>
  <moldb-polarizability>122.88155630628849</moldb-polarizability>
  <moldb-rotatable-bond-count>11</moldb-rotatable-bond-count>
  <moldb-acceptor-count>16</moldb-acceptor-count>
  <moldb-donor-count>5</moldb-donor-count>
  <moldb-pka-strongest-acidic>4.554611154731956</moldb-pka-strongest-acidic>
  <moldb-pka-strongest-basic>-1.7897215412581988</moldb-pka-strongest-basic>
  <moldb-physiological-charge>-1</moldb-physiological-charge>
  <moldb-number-of-rings>10</moldb-number-of-rings>
  <moldb-alogps-logp>3.75</moldb-alogps-logp>
  <moldb-alogps-logs>-5.58</moldb-alogps-logs>
  <moldb-alogps-solubility>2.84e-03 g/l</moldb-alogps-solubility>
</compound>
