aplysiatoxin

Also known as (1S,3R,4S,5S,9R,13S,14R)-3-[(2S,5S)-5-(2-bromo-5-hydroxyphenyl)-5-methoxypentan-2-yl]-13-hydroxy-9-[(1R)-1-hydroxyethyl]-4,14,16,16-tetramethyl-2,6,10,17-tetraoxatricyclo[11.3.1.1¹,⁵]octadecane-7,11-dione

Aplysiatoxin is a cyanotoxin produced by certain cyanobacteria species. It is used as a defensive secretion to protect these cyanobacteria from predation by fish, being a potent irritant and carcinogen, by acting as a powerful activator of protein kinase C. While this action has a tumour-promoting effect, protein kinase C activation can be medically beneficial for some other applications, and synthetic analogues of aplysiatoxin have been researched for anti-cancer effects.

Chemical data

Formula: C32H47BrO10
Molecular weight: 671.6 g/mol
IUPAC name: (1S,3R,4S,5S,9R,13S,14R)-3-[(2S,5S)-5-(2-bromo-5-hydroxyphenyl)-5-methoxypentan-2-yl]-13-hydroxy-9-[(1R)-1-hydroxyethyl]-4,14,16,16-tetramethyl-2,6,10,17-tetraoxatricyclo[11.3.1.11,5]octadecane-7,11-dione
SMILES: C[C@@H]1CC([C@@]23C[C@@H]([C@@H]([C@H](O2)[C@@H](C)CC[C@@H](C4=C(C=CC(=C4)O)Br)OC)C)OC(=O)C[C@@H](OC(=O)C[C@@]1(O3)O)[C@@H](C)O)(C)C
InChIKey: RHJPBGWFGOAEID-BEDNPZBZSA-N
XLogP: 4.8
Polar surface area: 141 Å²
H-bond donors: 3
H-bond acceptors: 10
Formal charge: 0

via PubChem

Wikidata facts

Mass: 670.235259804

Show 3 more facts

canonical SMILES: O=C1OC2CC3(OC(C(C)CCC(OC)C4=CC(O)=CC=C4Br)C2C)OC(O)(CC(=O)OC(C1)C(O)C)C(C)CC3(C)C
isomeric SMILES: CO[C@@H](CC[C@H](C)[C@H]1O[C@@]23C[C@H](OC(=O)C[C@H]([C@@H](C)O)OC(=O)C[C@](O)(O2)[C@H](C)CC3(C)C)[C@@H]1C)c1cc(O)ccc1Br
chemical formula: C₃₂H₄₇BrO₁₀

Sources (1)