Jasplakinolide

Jasplakinolide

Names
IUPAC name Cyclo[(3R)-3-(4-hydroxyphenyl)-β-alanyl-(2S,4E,6R,8S)-8-hydroxy-2,4,6-trimethyl-4-nonenoyl-L-alanyl-2-bromo-N-methyl-D-tryptophyl]
Identifiers
CAS Number	102396-24-7
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL257166
ChemSpider	52563404
KEGG	C16883
PubChem CID	9831636
InChI InChI=1S/C36H45BrN4O6/c1-20-15-21(2)17-23(4)47-32(43)19-30(25-11-13-26(42)14-12-25)40-35(45)31(18-28-27-9-7-8-10-29(27)39-33(28)37)41(6)36(46)24(5)38-34(44)22(3)16-20/h7-15,21-24,30-31,39,42H,16-19H2,1-6H3,(H,38,44)(H,40,45)/b20-15+/t21-,22-,23-,24-,30+,31+/m0/s1 Key: GQWYWHOHRVVHAP-DHKPLNAMSA-N
SMILES C[C@@H]\1C[C@@H](OC(=O)C[C@@H](NC(=O)[C@H](N(C(=O)[C@@H](NC(=O)[C@H](C/C(=C1)/C)C)C)C)CC2=C(NC3=CC=CC=C32)Br)C4=CC=C(C=C4)O)C
Properties
Chemical formula	C36H45BrN4O6
Molar mass	709.682 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

Jasplakinolide is a naturally occurring cyclo-depsipeptide. It was first isolated from a species of marine sponge named Jaspis johnstoni. It is permeable to the cell membrane meaning that it is able to cross the membrane.^[1] Once it crosses the cell membrane, it is a potent inducer and stabilizer of actin filaments meaning that it rapidly stabilizes pre-existing filaments and polymerize the protein actin.^[2] It also inhibits the disassembly of theses filaments. When doing this, it competes with phalloidin making it unable to bind with F-actin.^[3]