Symplocamide A

Symplocamide A
Names
	IUPAC name N1-[(2S,5S,8S,11R,12S,15S,18S,21R)-5-(3-bromo-4-methoxybenzyl)-2-[(2S)-butan-2-yl]-15-[3-(carbamoylamino)propyl]-21-hydroxy-4,11-dimethyl-3,6,9,13,16,22-hexaoxo-8-(propan-2-yl)-10-oxa-1,4,7,14,17-pentaazabicyclo[16.3.1]docos-12-yl]-N2-butanoyl-L-glutamamide
Identifiers
CAS Number	1007391-44-7 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL436840;
ChemSpider	23314421 ;
PubChem CID	44448139;
CompTox Dashboard (EPA)	DTXSID40659157 ;
	InChI InChI=1S/C46H71BrN10O13/c1-9-12-34(59)51-29(15-18-33(48)58)40(62)55-37-25(6)70-45(67)36(23(3)4)54-41(63)31(22-26-14-17-32(69-8)27(47)21-26)56(7)44(66)38(24(5)10-2)57-35(60)19-16-30(43(57)65)53-39(61)28(52-42(37)64)13-11-20-50-46(49)68/h14,17,21,23-25,28-31,35-38,60H,9-13,15-16,18-20,22H2,1-8H3,(H2,48,58)(H,51,59)(H,52,64)(H,53,61)(H,54,63)(H,55,62)(H3,49,50,68)/t24-,25 ,28-,29-,30-,31-,35 ,36-,37-,38-/m0/s1 Key: XFQCUAOQRAZAJB-APLIVAFESA-N;
	SMILES CCCC(=O)N[C@@H](CCC(=O)N)C(=O)N[C@H]1[C@H](OC(=O)[C@@H](NC(=O)[C@@H](N(C(=O)[C@@H](N2[C@@H](CC[C@@H](C2=O)NC(=O)[C@@H](NC1=O)CCCNC(=O)N)O)[C@@H](C)CC)C)Cc3ccc(c(c3)Br)OC)C(C)C)C;
Properties
Chemical formula	C46H71BrN10O13
Molar mass	1052.035 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

Symplocamide A is a newly discovered (2008) 3-amino-6-hydroxy-2-piperidone (Ahp) cyclodepsipeptide that has been isolated from a marine cyanobacteria in Papua New Guinea, which has only been identified at the genus level (Symploca).^[2] Cyanobacteria, both freshwater and marine, are known as producers of diverse protease inhibitors that may be used to treat diseases, such as HIV, and some forms of cancer. Research on symplocamide A has shown that it is a strong serine protease inhibitor and has a high level of cytotoxicity to cancer cells when used in vitro.^[3] As of the time of this writing, its use as a treatment on human participants has not been done and future study will have to be done before any human testing can be commenced.

^ Chemspider http://www.chemspider.com/Chemical-Structure.23314421.html
^ Stolze, Sara C.; Michael Meltzer; Michael Ehrmann; Markus Kaiser (27 September 2010). "Solid phase total synthesis of the 3-amino-6-hydroxy-2-piperidone (Ahp) cyclodepsipeptide and protease inhibitor Symplocamide A". Chemical Communications. 46 (46): 8857–8859. doi:10.1039/c0cc02889d. PMID 20967347. S2CID 36924580.
^ Linington, Roger G.; Daniel J. Edwards; Cynthia F. Shuman; Kerry L. McPhail; Teatulohi Matainaho; William H. Gerwick (2007). "Symplocamide A, a potent cytotoxin and chymotrypsin inhibitor from the marine cyanobacterium Symploca sp". Journal of Natural Products. 71 (1): 22–27. doi:10.1021/np070280x. PMC 2832912. PMID 18163584.

[Chemspider-1] Chemspider http://www.chemspider.com/Chemical-Structure.23314421.html

[2] Stolze, Sara C.; Michael Meltzer; Michael Ehrmann; Markus Kaiser (27 September 2010). "Solid phase total synthesis of the 3-amino-6-hydroxy-2-piperidone (Ahp) cyclodepsipeptide and protease inhibitor Symplocamide A". Chemical Communications. 46 (46): 8857–8859. doi:10.1039/c0cc02889d. PMID 20967347. S2CID 36924580.

[Linington_2007_22–27-3] Linington, Roger G.; Daniel J. Edwards; Cynthia F. Shuman; Kerry L. McPhail; Teatulohi Matainaho; William H. Gerwick (2007). "Symplocamide A, a potent cytotoxin and chymotrypsin inhibitor from the marine cyanobacterium Symploca sp". Journal of Natural Products. 71 (1): 22–27. doi:10.1021/np070280x. PMC 2832912. PMID 18163584.

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