Plakohypaphorine
Encyclopedia
Plakohypaphorines are iodine
-containing indole
alkaloid
s named for their similarity to hypaphorine, another alkaloid related to the amino acid
tryptophan
. First reported in the Caribbean
sponge Plakortis simplex in 2003, plakohypaphorines A-C were the first iodine-containing compounds based on the indole ring structure 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.
Iodine
Iodine is a chemical element with the symbol I and atomic number 53. The name is pronounced , , or . The name is from the , meaning violet or purple, due to the color of elemental iodine vapor....
-containing indole
Indole
Indole is an aromatic heterocyclic organic compound. It has a bicyclic structure, consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. Indole is a popular component of fragrances and the precursor to many pharmaceuticals. Compounds that contain an...
alkaloid
Alkaloid
Alkaloids are a group of naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids...
s named for their similarity to hypaphorine, another alkaloid related to the amino acid
Amino acid
Amino acids are molecules containing an amine group, a carboxylic acid group and a side-chain that varies between different amino acids. The key elements of an amino acid are carbon, hydrogen, oxygen, and nitrogen...
tryptophan
Tryptophan
Tryptophan is one of the 20 standard amino acids, as well as an essential amino acid in the human diet. It is encoded in the standard genetic code as the codon UGG...
. First reported in the Caribbean
Caribbean
The Caribbean is a crescent-shaped group of islands more than 2,000 miles long separating the Gulf of Mexico and the Caribbean Sea, to the west and south, from the Atlantic Ocean, to the east and north...
sponge Plakortis simplex in 2003, plakohypaphorines A-C were the first iodine-containing compounds based on the indole ring structure 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 IUPAC nomenclature A chemical nomenclature is a set of rules to generate systematic names for chemical compounds. The nomenclature used most frequently worldwide is the one created and developed by the International Union of Pure and Applied Chemistry .... |
Chemical formula Chemical formula A chemical formula or molecular formula is a way of expressing information about the atoms that constitute a particular chemical compound.... |
SMILES Simplified molecular input line entry specification The simplified molecular-input line-entry specification or SMILES is a specification in form of a line notation for describing the structure of chemical molecules using short ASCII strings... |
Image |
|---|---|---|---|---|
| Plakohypaphorine | 7-Iodo-N,N,N-trimethyltryptophan | C14H17IN2O2 | OC(=O)C(N(C)(C)C)Cc2cnc1c2cccc1I |  |
| Plakohypaphorine B | 6,7-Diiodo-N,N,N-trimethyltryptophan | C14H16I2N2O2 | OC(=O)C(N(C)(C)C)Cc2cnc1c2ccc(I)c1I |  |
| Plakohypaphorine C | 5,7-Diiodo-N,N,N-trimethyltryptophan | C14H16I2N2O2 | CN(C)(C)C(C(=O)O)Cc2cnc1c2cc(I)cc1I |  |
| Plakohypaphorine D | 5,6-Diiodo-N,N,N-trimethyltryptophan | C14H16I2N2O2 | Ic2cc1c(cc2I)ncc1CC(C(O)=O)N(C)(C)C |  |
| Plakohypaphorine E | 5,6,7-Triiodo-N,N,N-trimethyltryptophan | C14H15I3N2O2 | CN(C)(C)C(C(=O)O)Cc1cnc(c(I)c2I)c1cc2I |  |
| Plakohypaphorine F | 6-Chloro-5-iodo-N,N,N-trimethyltryptophan | C14H16ClIN2O2 | Clc2c1ncc(CC(C(O)=O)N(C)(C)C)c1cc(I)c2 |  |