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Compounds

COMPOUND NPA002977

STRUCTURE
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PROPERTIES
NPAID NPA002977
CLUSTER ID 279
NODE ID 253
NAME Gliocladine C
FORMULA C23H20N4O3S2
MOLECULAR WEIGHT (Da) 464.5720
ACCURATE MASS (Da) 464.0977
ORIGIN ORGANISM TYPE Fungus
ORIGIN GENUS Gliocladium
ORIGIN SPECIES roseum
InChIKey MRBZKCMQZBKXMZ-PHXJMUFTSA-N
InChI InChI=1S/C23H20N4O3S2/c1-21-19(29)27-18-22(13-8-4-6-10-16(13)25-18,14-11-24-15-9-5-3-7-12(14)15)17(28)23(27,32-31-21)20(30)26(21)2/h3-11,17-18,24-25,28H,1-2H3/t17-,18+,21-,22+,23-/m0/s1
SMILES C[C@]12C(=O)N3[C@@H]4[C@]([C@@H]([C@@]3(C(=O)N1C)SS2)O)(C5=CC=CC=C5N4)C6=CNC7=CC=CC=C76
ORIGINAL ISOLATION REFERENCE
CITATION Dong, Jin-Yan; He, Hong-Ping; Shen, Yue-Mao; Zhang, Ke-Qin Nematicidal epipolysulfanyldioxopiperazines from Gliocladium roseum Journal of Natural Products 2005 68 (10) 1510-1513.
DOI 10.1021/np0502241 PMID 16252916
ORIGINAL ISOLATION TAXONOMY
RANK NAME DB LINK NCBI
Domain Eukarya - 2759
Kingdom Fungi MycoBank 4751
Phylum Ascomycota MycoBank 4890
Class Sordariomycetes MycoBank 147550
Order Hypocreales MycoBank 5125
Family Hypocreaceae MycoBank 5129
Genus Gliocladium MycoBank 62887
SYNTHESES
CITATION 1 DeLorbe JE; Jabri SY; Mennen SM; Overman LE; Zhang FL Enantioselective total synthesis of (+)-gliocladine C: convergent construction of cyclotryptamine-fused polyoxopiperazines and a general approach for preparing epidithiodioxopiperazines from trioxopiperazine precursors. Journal of the American Chemical Society 2011 133 (17) 6549-6552. DOI: 10.1021/ja201789v PMID: 21473649
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