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Substance Name: Lophotoxin
RN: 78697-56-0
UNII: 6LL2IET058
InChIKey: KGRIGHVGXOOCOY-ALYDTWDZSA-N

Note

  • Belongs to the cembrene class of diterpenoids; neuromuscular toxin isolated from several pacific gorgonians of the genus Lophogorgia.

Molecular Formula

  • C22-H24-O8

Molecular Weight

  • 416.424
 

Classification Codes

  • Drug / Therapeutic Agent
  • Natural Product
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Names and Synonyms

Name of Substance

  • Lophotoxin

Synonyms

  • BRN 4339458
  • Lophotoxin
  • UNII-6LL2IET058

Systematic Names

  • 11,16,18,19-Tetraoxapentacyclo(12.2.2.1(sup 6,9).0(sup 1,15).0(10,12))nonadeca-6,8-diene-7-carboxaldehyde, 2-(acetyloxy)-12-methyl-4-(1-methylethenyl)-17-oxo-, (1R-(1R*,2S*,4S*,10R*,12R*,14R*,15R*))-
  • 11,16,18,19-Tetraoxapentacyclo(12.2.2.16,9.01,15.010,12)nonadeca-6,8-diene-7-carboxaldehyde, 2-(acetyloxy)-12-methyl-4-(1-methylethenyl)-17-oxo-, (1R,2S,4S,10R,12R,14R,15R)-
  • 11,16,18,19-Tetraoxapentacyclo(12.2.2.16,9.01,15.010,12)nonadeca-6,8-diene-7-carboxaldehyde, 2-(acetyloxy)-12-methyl-4-(1-methylethenyl)-17-oxo-, (1R-(1R*,2S*,4S*,10R*,12R*,14R*,15R*))-

Registry Numbers

CAS Registry Number

  • 78697-56-0

FDA UNII

  • 6LL2IET058

System Generated Number

  • 0078697560

Structure Descriptors

InChI

1S/C22H24O8/c1-10(2)12-5-14-13(9-23)6-15(27-14)18-21(4,29-18)8-16-19-22(30-19,20(25)28-16)17(7-12)26-11(3)24/h6,9,12,16-19H,1,5,7-8H2,2-4H3/t12-,16-,17+,18+,19-,21-,22-/m1/s1

InChIKey

KGRIGHVGXOOCOY-ALYDTWDZSA-N

Smiles

C1(=O)O[C@@H]2C[C@@]3([C@@H](O3)c3oc(C[C@@H](C(C)=C)C[C@@H]([C@@]41[C@H]2O4)OC(C)=O)c(c3)C=O)C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 8mg/kg (8mg/kg)   Annual Review of Pharmacology and Toxicology. Vol. 26, Pg. 117, 1986.
mouse LD50 subcutaneous 8mg/kg (8mg/kg) BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE)
Science. Vol. 212, Pg. 1512, 1981.