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Compounds

COMPOUND NPA017485

STRUCTURE
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EXTERNAL LINKS
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PROPERTIES
NPAID NPA017485
CLUSTER ID 83
NODE ID 78
NAME Gliotoxin
FORMULA C13H14N2O4S2
MOLECULAR WEIGHT (Da) 326.3990
ACCURATE MASS (Da) 326.0395
ORIGIN ORGANISM TYPE Fungus
ORIGIN GENUS Gliocladium
ORIGIN SPECIES fimbriatum
InChIKey FIVPIPIDMRVLAY-HIAZDOBYSA-N
InChI InChI=1S/C13H14N2O4S2/c1-14-10(18)12-5-7-3-2-4-8(17)9(7)15(12)11(19)13(14,6-16)21-20-12/h2-4,8-9,16-17H,5-6H2,1H3/t8-,9+,12+,13+/m0/s1
SMILES CN1C(=O)[C@]23CC4=CC=C[C@@H]([C@@H]4N2C(=O)[C@]1(SS3)CO)O
ORIGINAL ISOLATION REFERENCE
CITATION Bell, Malcolm R; Johnson, John R; Wildi, Bernard S; Woodward, RB The structure of gliotoxin Journal of the American Chemical Society 1958 80 (4) 1001-1001.
DOI 10.1021/ja01537a065 PMID -
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 Nicolaou KC; Lu M; Totokotsopoulos S; Heretsch P; Giguère D; Sun YP; Sarlah D; Nguyen TH; Wolf IC; Smee DF; Day CW; Bopp S; Winzeler EA Synthesis and biological evaluation of epidithio-, epitetrathio-, and bis-(methylthio)diketopiperazines: synthetic methodology, enantioselective total synthesis of epicoccin G, 8,8'-epi-ent-rostratin B, gliotoxin, gliotoxin G, emethallicin E, and haematocin and discovery of new antiviral and antimalarial agents. Journal of the American Chemical Society 2012 134 (41) 17320-17332. DOI: 10.1021/ja308429f PMID: 22978674
CITATION 2 Fukuyama T; Kishi Y A total synthesis of gliotoxin. Journal of the American Chemical Society 1976 98 (21) 6723-4. DOI: 10.1021/ja00437a063 PMID: 61223
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