Plakohypaphorine

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Plakohypaphorines are halogenated indolic non-proteinogenic amino acids named for their similarity to hypaphorine (N,N,N-trimethyltryptophan betaine). First reported in the Caribbean sponge Plakortis simplex in 2003, plakohypaphorines A-C were the first iodine-containing indole alkaloids to be discovered in nature. Plakohypaphorines D-F, also found in P. simplex, were reported in 2004 by a group including the researchers who discovered the original plakohypaphorines.

Plakohypaphorine Chemical name Chemical formula SMILES Image
Plakohypaphorine7-Iodo-N,N,N-trimethyltryptophanC14H17IN2O2OC(=O)C(N(C)(C)C)Cc2cnc1c2cccc1I Plakohypaphorine A.svg
Plakohypaphorine B6,7-Diiodo-N,N,N-trimethyltryptophanC14H16I2N2O2OC(=O)C(N(C)(C)C)Cc2cnc1c2ccc(I)c1I Plakohypaphorine B.svg
Plakohypaphorine C5,7-Diiodo-N,N,N-trimethyltryptophanC14H16I2N2O2CN(C)(C)C(C(=O)O)Cc2cnc1c2cc(I)cc1I Plakohypaphorine C.svg
Plakohypaphorine D5,6-Diiodo-N,N,N-trimethyltryptophanC14H16I2N2O2Ic2cc1c(cc2I)ncc1CC(C(O)=O)N(C)(C)C Plakohypaphorine D.svg
Plakohypaphorine E5,6,7-Triiodo-N,N,N-trimethyltryptophanC14H15I3N2O2CN(C)(C)C(C(=O)O)Cc1cnc(c(I)c2I)c1cc2I Plakohypaphorine E.svg
Plakohypaphorine F6-Chloro-5-iodo-N,N,N-trimethyltryptophanC14H16ClIN2O2Clc2c1ncc(CC(C(O)=O)N(C)(C)C)c1cc(I)c2 Plakohypaphorine F.svg

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