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Compounds

COMPOUND NPA018872

STRUCTURE
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PROPERTIES
NPAID NPA018872
CLUSTER ID 275
NODE ID 249
NAME Dendroamide A
FORMULA C21H24N6O4S2
MOLECULAR WEIGHT (Da) 488.5950
ACCURATE MASS (Da) 488.1300
ORIGIN ORGANISM TYPE Bacterium
ORIGIN GENUS Stigonema
ORIGIN SPECIES dendroideum
InChIKey MDIRDFOZMJDCMK-GPCCPHFNSA-N
InChI InChI=1S/C21H24N6O4S2/c1-8(2)14-21-25-13(7-33-21)17(29)23-10(4)20-24-12(6-32-20)16(28)22-9(3)19-27-15(11(5)31-19)18(30)26-14/h6-10,14H,1-5H3,(H,22,28)(H,23,29)(H,26,30)/t9-,10-,14-/m1/s1
SMILES C[C@@H]1C2=NC(=C(O2)C)C(=O)N[C@@H](C3=NC(=CS3)C(=O)N[C@@H](C4=NC(=CS4)C(=O)N1)C)C(C)C
ORIGINAL ISOLATION REFERENCE
CITATION Ogino, Junichi; Moore, Richard E.; Patterson, Gregory M. L.; Smith, Charles D. Dendroamides, new cyclic hexapeptides from a blue-green alga. Multidrug- resistance reversing activity of dendroamide A Journal of Natural Products 1996 59 (6) 581-586.
DOI 10.1021/np960178s PMID 8786364
ORIGINAL ISOLATION TAXONOMY
RANK NAME DB LINK NCBI
Domain Bacteria LPSN 2
Phylum Cyanobacteria LPSN 1117
Class Cyanophyceae LPSN -
Order Nostocales LPSN 1161
Family Stigonemataceae LPSN 1189
Genus Stigonema LPSN 221292
SYNTHESES
CITATION 1 You SL; Kelly JW Total synthesis of dendroamide a: oxazole and thiazole construction using an oxodiphosphonium salt. Journal of Organic Chemistry 2003 68 (24) 9506-9509. DOI: 10.1021/jo0302657 PMID: 14629183
CITATION 2 Xia Z; Smith CD Total synthesis of dendroamide A, a novel cyclic peptide that reverses multiple drug resistance. Journal of Organic Chemistry 2001 66 (10) 3459-3466. DOI: 10.1021/jo005783l PMID: 11348130
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