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Substance Name: Ciguatoxin
RN: 11050-21-8
UNII: 2UKQ3B7696
InChIKey: VYVRIXWNTVOIRD-LRHBOZQDSA-N

Note

  • Polycyclic ethers produced by Gambierdiscus (DINOFLAGELLATES) from gambiertoxins, which are ingested by fish which in turn may be ingested by humans who are susceptible to the CIGUATERA POISONING.

Molecular Formula

  • C60-H86-O19

Molecular Weight

  • 1111.3204
 

Classification Codes

  • Natural Product
  • Noxae
  • Poisons
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Names and Synonyms

Name of Substance

  • Ciguatoxin

MeSH Heading

  • Ciguatoxins

Synonyms

  • Ciguatoxin
  • Ciguatoxin 1
  • Ciguatoxin CTX 1
  • CTX 1
  • HSDB 7241
  • P-CTX 1
  • Pacific ciguatoxin 1
  • UNII-2UKQ3B7696

Systematic Names

  • Ciguatoxin
  • Spiro(furan-2(3H),2'(3'H)-oxepino(2'''',3'''':5''',6''')pyrano(2''',3''':5'',6'')pyrano(2'',3'':6',7')oxepino(2',3':6,7)oxepino(3,2-b)pyrano(2''''',3''''':6'''',7'''')oxepino(2'''',3'''':5''',6''')pyrano(2''',3''':7'',8'')oxocino(2'',3'':5',6')pyrano(2',3':6,7)oxepino(2,3-h)oxonin), ciguatoxin deriv.

Registry Numbers

CAS Registry Number

  • 11050-21-8

FDA UNII

  • 2UKQ3B7696

System Generated Number

  • 0011050218

Structure Descriptors

InChI

1S/C60H86O19/c1-28-19-42-44(22-48-54(76-42)30(3)52(65)58-55(77-48)29(2)31(4)60(79-58)25-33(63)27-67-60)73-46-24-51-59(5,78-47(46)20-28)50(64)23-45-36(74-51)11-7-6-10-35-37(71-45)15-16-39-38(69-35)17-18-40-43(70-39)21-49-57(75-40)53(66)56-41(72-49)12-8-9-34(68-56)14-13-32(62)26-61/h6-9,13-18,28-58,61-66H,10-12,19-27H2,1-5H3/b7-6-,14-13+/t28-,29+,30+,31+,32+,33+,34-,35-,36+,37+,38+,39-,40-,41+,42+,43+,44-,45-,46+,47-,48+,49-,50-,51-,52+,53-,54-,55-,56+,57-,58+,59+,60-/m1/s1

InChIKey

VYVRIXWNTVOIRD-LRHBOZQDSA-N

Smiles

C[C@@H]1C[C@H]2[C@@H](C[C@H]3[C@H](O2)[C@H]([C@@H]([C@H]4[C@H](O3)[C@H]([C@@H]([C@]5(O4)C[C@@H](CO5)O)C)C)O)C)O[C@H]6C[C@@H]7[C@]([C@@H](C[C@@H]8[C@@H](O7)C/C=C\C[C@@H]9[C@@H](O8)C=C[C@@H]2[C@@H](O9)C=C[C@@H]3[C@@H](O2)C[C@@H]2[C@@H](O3)[C@@H]([C@@H]3[C@@H](O2)CC=C[C@@H](O3)/C=C/[C@@H](CO)O)O)O)(O[C@@H]6C1)C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
chicken LD50 intraperitoneal 80mg/kg (80mg/kg)   Proceedings of the Western Pharmacology Society. Vol. 11, Pg. 126, 1968.
chicken LD50 intravenous 10600ug/kg (10.6mg/kg)   Proceedings of the Western Pharmacology Society. Vol. 11, Pg. 126, 1968.
chicken LD50 oral 8800ug/kg (8.8mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: ATAXIA
Bulletin de la Societe de Pathologie Exotique et de Ses Filiales. Vol. 79, Pg. 140, 1986.
mouse LD50 intraperitoneal 250ng/kg (0.00025mg/kg)   Toxicon. Vol. 29, Pg. 1115, 1991.
mouse LD50 oral 530mg/kg (530mg/kg) BEHAVIORAL: ATAXIA

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: CYANOSIS
Toxicon. Vol. 6, Pg. 131, 1968.
mouse LD50 unreported 450ng/kg (0.00045mg/kg)   Yakkyoku. Pharmacy. Vol. 38, Pg. 1213, 1987.
rat LD50 intravenous 11mg/kg (11mg/kg) CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION)

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION
Toxicon. Vol. 6, Pg. 55, 1968.