Psymberin information

Psymberin
Names
	IUPAC name (2S,3S)-N-((S)-((2S,4R,6R)-6-((2S,3R)-3-((R)-6,8-dihydroxy-5-methyl-1-oxoisochroman-3-yl)-2-hydroxybutyl)-4-hydroxy-5,5-dimethyltetrahydro-2H-pyran-2-yl)(methoxy)methyl)-2-hydroxy-3-methoxy-5-methylhex-5-enamide
	Other names irciniastatin A
Identifiers
CAS Number	714954-37-7;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL374598;
ChemSpider	24604808;
PubChem CID	11692946;
	InChI InChI=1S/C31H47NO11/c1-14(2)9-22(40-7)27(37)28(38)32-29(41-8)23-13-24(36)31(5,6)25(42-23)12-19(34)16(4)21-10-17-15(3)18(33)11-20(35)26(17)30(39)43-21/h11,16,19,21-25,27,29,33-37H,1,9-10,12-13H2,2-8H3,(H,32,38)/t16-,19+,21-,22+,23+,24-,25-,27+,29+/m1/s1 Key: BNNIEBYABSNREN-CYRUSRGFSA-N;
	SMILES O[C@@H](C[C@H]1O[C@H]([C@H](OC)NC([C@@H](O)[C@H](CC(C)=C)OC)=O)C[C@@H](O)C1(C)C)[C@@H](C)[C@@H](CC2=C(C)C(O)=CC(O)=C23)OC3=O;
Properties
Chemical formula	C31H47NO11
Molar mass	609.71 g/mol
Appearance	clear, glasslike solid
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Psymberin, also known as irciniastatin A, is a cytotoxin derived from sea sponges. It was discovered by two independent research groups, one led by Dr. Phil Crews and one led by Dr. Jean Schmidt, in 2004.^[1]^[2] Psymberin was found to be highly bioactive as it showed LC50s at nanomolar concentrations against various types of tumors.^[1]^[2]

^ ^a ^b ^c Cichewicz RH, Valeriote FA, Crews P (2004). "Psymberin, a potent sponge-derived cytotoxin from Psammocinia distantly related to the pederin family". Org. Lett. 6 (12): 1951–4. doi:10.1021/ol049503q. PMID 15176791.
^ ^a ^b Pettit GR, Xu JP, Chapuis JC, Pettit RK, Tackett LP, Doubek DL, Hooper JN, Schmidt JM (2004). "Antineoplastic agents. 520. Isolation and structure of irciniastatins A and B from the Indo-Pacific marine sponge Ircinia ramosa". J. Med. Chem. 47 (5): 1149–52. doi:10.1021/jm030207d. PMID 14971894.

[Cichewicz2004-1] Cichewicz RH, Valeriote FA, Crews P (2004). "Psymberin, a potent sponge-derived cytotoxin from Psammocinia distantly related to the pederin family". Org. Lett. 6 (12): 1951–4. doi:10.1021/ol049503q. PMID 15176791.

[pmid14971894-2] Pettit GR, Xu JP, Chapuis JC, Pettit RK, Tackett LP, Doubek DL, Hooper JN, Schmidt JM (2004). "Antineoplastic agents. 520. Isolation and structure of irciniastatins A and B from the Indo-Pacific marine sponge Ircinia ramosa". J. Med. Chem. 47 (5): 1149–52. doi:10.1021/jm030207d. PMID 14971894.

Psymberin information

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Psymberin

Pederin

Krische allylation

Phillip Crews