Portimine A

Portimine A is a cyclic imine natural product produced by the dinoflagellate microalgae Vulcanodinium rugosum. It is a drug lead due to its anti-cancer activity.^[1] It seemingly inhibits ribosomal translation activity through an interaction with NMD3,^[1] leading to activation of the inflammasome.^[2] It is suspected to be causal toxin behind an severe inflammatory skin disease in Senegalese fishermen in 2020 and 2021.^[2]

Quick facts Names, Identifiers ...

Portimine A

Names
IUPAC name (3aR,7aS,8S,10R,12S,13S,16R,18S)-10,18-dihydroxy-12-methyl-6-vinyl-2,3,4,5,7a,8,10,11,12,13,14,15,17,18-tetradecahydro-9H-8,16:13,16-diepoxybenzo[2,3]cyclotetradeca[1,2-b]pyrrol-9-one
Identifiers
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL4467341
ChemSpider	30771030
PubChem CID	72197887
InChI InChI=1S/C23H31NO5/c1-3-14-4-6-22-8-9-24-21(22)17(26)12-23-7-5-18(28-23)13(2)10-16(25)19(27)20(29-23)15(22)11-14/h3,11,13,15-18,20,25-26H,1,4-10,12H2,2H3/t13-,15+,16+,17-,18-,20-,22+,23+/m0/s1 Key: JYQBXOZZPLFICX-CPWUQFAPSA-N
SMILES C[C@H]1C[C@H](C(=O)[C@@H]2[C@H]3C=C(CC[C@@]34CCN=C4[C@H](C[C@]5(O2)CC[C@@H]1O5)O)C=C)O
Properties
Chemical formula	C23H31NO5
Molar mass	401.503 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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