Antillatoxin

Antillatoxin

Three-dimensional representation of antillatoxin
Names
IUPAC name
(6S,9S,14R,15R)-7,9,14-Trimethyl-13-methylidene-6-propan-2-yl-15-[(2E,4E)-4,6,6-trimethylhepta-2,4-dien-2-yl]-1-oxa-4,7,10-triazacyclopentadecane-2,5,8,11-tetrone
Other names
ATX
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
  • InChI=1S/C27H43N3O5/c1-16(2)23-25(33)28-15-22(32)35-24(17(3)12-11-13-27(7,8)9)19(5)18(4)14-21(31)29-20(6)26(34)30(23)10/h11-13,16,19-20,23-24H,4,14-15H2,1-3,5-10H3,(H,28,33)(H,29,31)/b13-11+,17-12+/t19-,20+,23+,24+/m1/s1
    Key: TYCMYIZCBRIDDR-GHGXTVDISA-N
  • InChI=1/C27H43N3O5/c1-16(2)23-25(33)28-15-22(32)35-24(17(3)12-11-13-27(7,8)9)19(5)18(4)14-21(31)29-20(6)26(34)30(23)10/h11-13,16,19-20,23-24H,4,14-15H2,1-3,5-10H3,(H,28,33)(H,29,31)/b13-11+,17-12+/t19-,20+,23+,24+/m1/s1
    Key: TYCMYIZCBRIDDR-GHGXTVDIBQ
  • C[C@H]1[C@@H](OC(=O)CNC(=O)[C@@H](N(C(=O)[C@@H](NC(=O)CC1=C)C)C)C(C)C)/C(=C/C=C/C(C)(C)C)/C
Properties
C28H45N3O5
Molar mass 503.674
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Antillatoxin (ATX) is a potent lipopeptide neurotoxin produced by the marine cyanobacterium Lyngbya majuscula. ATX activates voltage-gated sodium channels, which can cause cell depolarisation, NMDA-receptor overactivity, excess calcium influx and neuronal necrosis.


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