Plakohypaphorine
Plakohypaphorines are halogenated indolic non-proteinogenic amino acids named for their similarity to hypaphorine. 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 |
| Plakohypaphorine | 7-Iodo-N,N,N-trimethyltryptophan | C14H17IN2O2 | OCCCc2cnc1c2cccc1I | |
| Plakohypaphorine B | 6,7-Diiodo-N,N,N-trimethyltryptophan | C14H16I2N2O2 | OCCCc2cnc1c2cccc1I | |
| Plakohypaphorine C | 5,7-Diiodo-N,N,N-trimethyltryptophan | C14H16I2N2O2 | CNCCc2cnc1c2cccc1I | |
| Plakohypaphorine D | 5,6-Diiodo-N,N,N-trimethyltryptophan | C14H16I2N2O2 | Ic2cc1cncc1CCNC | |
| Plakohypaphorine E | 5,6,7-Triiodo-N,N,N-trimethyltryptophan | C14H15I3N2O2 | CNCCc1cncc1cc2I | |
| Plakohypaphorine F | 6-Chloro-5-iodo-N,N,N-trimethyltryptophan | C14H16ClIN2O2 | Clc2c1nccc1ccc2 |