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Compounds

COMPOUND NPA002992

STRUCTURE
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PROPERTIES
NPAID NPA002992
CLUSTER ID 352
NODE ID 317
NAME Dolastatin 16
FORMULA C47H70N6O10
MOLECULAR WEIGHT (Da) 879.1090
ACCURATE MASS (Da) 878.5153
ORIGIN ORGANISM TYPE Bacterium
ORIGIN GENUS Lyngbya
ORIGIN SPECIES majuscula
InChIKey JXOFEBNJOOEXJY-NLKHYCKVSA-N
InChI InChI=1S/C47H70N6O10/c1-26(2)36-30(8)46(60)62-31(9)42(56)53-24-16-21-35(53)47(61)63-39(28(5)6)45(59)50(10)38(27(3)4)44(58)52-23-15-20-34(52)41(55)49-37(29(7)25-32-17-12-11-13-18-32)43(57)51-22-14-19-33(51)40(54)48-36/h11-13,17-18,26-31,33-39H,14-16,19-25H2,1-10H3,(H,48,54)(H,49,55)/t29?,30?,31-,33-,34-,35-,36?,37?,38+,39+/m0/s1
SMILES C[C@H]1C(=O)N2CCC[C@H]2C(=O)O[C@@H](C(=O)N([C@@H](C(=O)N3CCC[C@H]3C(=O)NC(C(=O)N4CCC[C@H]4C(=O)NC(C(C(=O)O1)C)C(C)C)C(C)CC5=CC=CC=C5)C(C)C)C)C(C)C
ORIGINAL ISOLATION REFERENCE
CITATION Nogle, Lisa M.; Gerwick, William H. Isolation of Four New Cyclic Depsipeptides, Antanapeptins A-D, and Dolastatin 16 from a Madagascan Collection of Lyngbya majuscula Journal of Natural Products 2002 65 (1) 21-24.
DOI 10.1021/np010348n PMID 11809058
ORIGINAL ISOLATION TAXONOMY
RANK NAME DB LINK NCBI
Domain Bacteria LPSN 2
Phylum Cyanobacteria LPSN 1117
Class Cyanophyceae LPSN -
Order Oscillatoriales LPSN 1150
Family Oscillatoriaceae LPSN 1892254
Genus Lyngbya LPSN 28073
SYNTHESES
CITATION 1 Pettit GR; Smith TH; Arce PM; Flahive EJ; Anderson CR; Chapuis JC; Xu JP; Groy TL; Belcher PE; Macdonald CB Antineoplastic agents. 599. Total synthesis of dolastatin 16. Journal of Natural Products 2015 78 (3) 476-85. DOI: 10.1021/np500925y PMID: 25689568
CITATION 2 Casalme LO; Yamauchi A; Sato A; Petitbois JG; Nogata Y; Yoshimura E; Okino T; Umezawa T; Matsuda F Total synthesis and biological activity of dolastatin 16. Organic & Biomolecular Chemistry 2017 15 (5) 1140-1150. DOI: 10.1039/c6ob02657e PMID: 28074955
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