Structure via PubChem · Public domain (PubChem)
teleocidin A1
Sign in to saveLyngbyatoxin-a is a type of alkaloid cyanotoxin produced by certain cyanobacteria species, most notably Moorea producens (formerly classified as Lyngbya majuscula). It is produced as defense mechanism to ward off any would-be predators of the bacterium, being a potent blister agent as well as carcinogen. Low concentrations cause a common skin condition known as seaweed dermatitis.
In the Vinony graph
Within Vinony's link graph, teleocidin A1 is referenced by 28 other articles, and connects out to digital object identifier, chemical formula and Cyanobacteria.
It is catalogued under topics including Bacterial alkaloids, Blister agents and Cyanotoxins.
Its subject is documented across 6 Wikipedia language editions.
Chemical data
- Formula
- C27H39N3O2
- Molecular weight
- 437.6 g/mol
- IUPAC name
- (10S,13S)-5-[(3R)-3,7-dimethylocta-1,6-dien-3-yl]-13-(hydroxymethyl)-9-methyl-10-propan-2-yl-3,9,12-triazatricyclo[6.6.1.04,15]pentadeca-1,4,6,8(15)-tetraen-11-one
- SMILES
- CC(C)[C@H]1C(=O)N[C@@H](CC2=CNC3=C(C=CC(=C23)N1C)[C@](C)(CCC=C(C)C)C=C)CO
- InChIKey
- KISDGNGREAJPQR-OICBGKIFSA-N
- XLogP
- 6.2
- Polar surface area
- 68.4 Ų
- H-bond donors
- 3
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Wikidata facts
- Mass
- 437.304
Show 4 more facts
- chemical formula
- C₂₇H₃₉N₃O₂
- canonical SMILES
- CC(C)C1C(=O)NC(CC2=CNC3=C(C=CC(=C23)N1C)C(C)(CCC=C(C)C)C=C)CO
- isomeric SMILES
- CC(C)[C@H]1C(=O)N[C@@H](CC2=CNC3=C(C=CC(=C23)N1C)[C@](C)(CCC=C(C)C)C=C)CO
- found in taxon
- Streptomyces
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
2 sectionsContents
- Biosynthesis
- References
Lyngbyatoxin-a is a type of alkaloid cyanotoxin produced by certain cyanobacteria species, most notably Moorea producens (formerly classified as Lyngbya majuscula). It is produced as defense mechanism to ward off any would-be predators of the bacterium, being a potent blister agent as well as carcinogen. Low concentrations cause a common skin condition known as seaweed dermatitis.
== Biosynthesis == thumb|Lyngbyatoxin Biosynthesis reported by Gerwick et al. and Neilan et al. Lyngbyatoxin is a terpenoid indole alkaloid hybrid that belongs to the class of non-ribosomal peptides (NRPs). Lyngbyatoxin contains a nucleophilic indole ring that takes part in the activation of protein kinases. Figure 1, shows the biosynthesis of Lyngbyatoxin reported by Neilan et al. and Gerwick et al. The non-ribosomal peptide synthase (NRPS) LtxA protein condenses L-methyl-valine and L-tryptophan to form the linear dipeptide N-methyl-L-valyl-L-tryptophan. The latter is released via a NADPH-dependent reductive cleavage to form the aldehyde which is subsequently reduced to the corresponding alcohol. A P450-dependent monooxygenase called LtxB then performs the oxidation and subsequent cyclization of N-methyl-L-valyl-L-tryptophan. Finally, LtxC transfers a geranyl functional group from geranyl pyrophosphate (GPP) to carbon number 7 of the indole ring.
Excerpted from Wikipedia’s “teleocidin A1” article, available under the CC BY-SA 4.0 licence.