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Substance Name: Lyngbyatoxin A
RN: 70497-14-2
UNII: SE69L721CS
InChIKey: KISDGNGREAJPQR-OICBGKIFSA-N

Note

  • Indole alkaloid from blue-green alga Lyngbya majuscula Gomont; responsible for dermatitis known as "swimmers' itch" in Hawaii.

Molecular Formula

  • C27-H39-N3-O2

Molecular Weight

  • 437.6241
 

Classification Codes

  • Drug / Therapeutic Agent
  • Natural Product
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Names and Synonyms

Name of Substance

  • Lyngbyatoxin A

Synonyms

  • CCRIS 4044
  • Lyngbyatoxin
  • Lyngbyatoxin A
  • Teleocidin A
  • Teleocidin A 1
  • UNII-SE69L721CS

Systematic Names

  • 3H-Pyrrolo(4,3,2-gh)-1,4-benzodiazonin-3-one, 1,2,4,5,6,8-hexahydro-9-(1-ethenyl-1,5-dimethyl-4-hexenyl)-5-(hydroxymethyl)-1-methyl-2-(1-methylethyl)-
  • 3H-Pyrrolo(4,3,2-gh)-1,4-benzodiazonin-3-one, 9-(1-ethenyl-1,5-dimethyl-4-hexenyl)-1,2,4,5,6,8-hexahydro-5-(hydroxymethyl)-1-methyl-2-(1-methylethyl)-
  • Teleocidin

Registry Numbers

CAS Registry Number

  • 70497-14-2

FDA UNII

  • SE69L721CS

Other Registry Number

  • 56645-57-9

System Generated Number

  • 0070497142

Structure Descriptors

InChI

1S/C27H39N3O2/c1-8-27(6,13-9-10-17(2)3)21-11-12-22-23-19(15-28-24(21)23)14-20(16-31)29-26(32)25(18(4)5)30(22)7/h8,10-12,15,18,20,25,28,31H,1,9,13-14,16H2,2-7H3,(H,29,32)/t20-,25-,27-/m0/s1

InChIKey

KISDGNGREAJPQR-OICBGKIFSA-N

Smiles

CC(C)[C@@H]1N(C)c2ccc(c3[nH]cc(C[C@@H](CO)NC1=O)c23)[C@](C)(CCC=C(C)C)C=C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intravenous 200ug/kg (0.2mg/kg)   Agricultural and Biological Chemistry. Vol. 26, Pg. 660, 1962.
mouse LD50 oral 2mg/kg (2mg/kg)   "Index of Antibiotics from Actinomycetes," Umezawa, H. et al., eds., Tokyo, Univ. of Tokyo Press, 1967Vol. -, Pg. 636, 1967.
mouse LDLo intraperitoneal 300ug/kg (0.3mg/kg)   Science. Vol. 204, Pg. 193, 1979.