Palau'amine

Palau'amine

Chemical structure of palau'amine
Names
Systematic IUPAC name 2,2'-Diamino-11-(aminomethyl)-12-chloro-1,1',3a,5',10a,11,12,13a-octahydro-5'-hydroxy-spiro[8H-cyclopenta[3,4]pyrrolo[1,2-a]imidazo[4,5-b]pyrrolo[1,2-d]pyrazine-13(10H),4'-[4H]imidazol]-8-one
Identifiers
CAS Number	148717-58-2
ChEMBL	ChEMBL2079438
ChemSpider	17279008
Jmol 3D model	Interactive image
MeSH	C438976
PubChem	16122048
InChI InChI=1S/C17H22ClN9O2/c18-10-6(4-19)7-5-27-11(28)8-2-1-3-26(8)12-17(27,25-14(20)22-12)9(7)16(10)13(29)23-15(21)24-16/h1-3,6-7,9-10,12-13,29H,4-5,19H2,(H3,20,22,25)(H3,21,23,24)/t6-,7-,9+,10+,12+,13+,16+,17-/m1/s1 Key: VYOQBYCIIJYKJA-VORKOXQSSA-N InChI=1/C17H22ClN9O2/c18-10-6(4-19)7-5-27-11(28)8-2-1-3-26(8)12-17(27,25-14(20)22-12)9(7)16(10)13(29)23-15(21)24-16/h1-3,6-7,9-10,12-13,29H,4-5,19H2,(H3,20,22,25)(H3,21,23,24)/t6-,7-,9+,10+,12+,13+,16+,17-/m1/s1 Key: VYOQBYCIIJYKJA-VORKOXQSBL
SMILES Cl[C@@H]4[C@@]1(NC(=N/[C@H]1O)\N)[C@H]3[C@@]26/N=C(\N[C@H]6n5c(C(=O)N2C[C@@H]3[C@H]4CN)ccc5)N
Properties
Chemical formula	C17H22ClN9O2
Molar mass	419.87 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

Palau'amine is a toxic alkaloid compound synthesized naturally by Stylotella agminata, a species of sea sponge found in the southwest Pacific Ocean. The name of the molecule derives from the island nation of Palau, near which the sponges are found.

The substance was first isolated and described in 1993. Containing nine nitrogen atoms, the molecule is considered highly complex. The precise atomic structure was pinned down in 2007, and two years later the molecule was synthesized in the lab by a team at the Scripps Research Institute in La Jolla, California.

Biosynthesis

A pathway to this dimeric pyrrole-imidazole alkaloid has been hypothesized to include a key oxidation of a β-ketoester with Mn(OAc)₃ initiated a cascade radical cyclization sequence to deliver an ageliferin skeleton.