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Compounds

COMPOUND NPA021227

STRUCTURE
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PROPERTIES
NPAID NPA021227
CLUSTER ID 2988
NODE ID 2287
NAME Rugulosin
FORMULA C30H22O10
MOLECULAR WEIGHT (Da) 542.4960
ACCURATE MASS (Da) 542.1213
ORIGIN ORGANISM TYPE Fungus
ORIGIN GENUS Sepedonium
ORIGIN SPECIES ampullosporum
InChIKey QFDPVUTXKUGISP-GBUXSVCISA-N
InChI InChI=1S/C30H22O10/c1-7-3-9-13(11(31)5-7)21(33)17-25(37)20-23(35)15-16-24(36)19(29(15,17)27(9)39)26(38)18-22(34)14-10(28(40)30(16,18)20)4-8(2)6-12(14)32/h3-6,15-16,19-20,23-24,31-36H,1-2H3/t15-,16-,19+,20+,23-,24-,29+,30+/m1/s1
SMILES CC1=CC(=C2C(=C1)C(=O)[C@]34[C@@H]5[C@@H]6[C@H]([C@H]3C(=O)C7=C(C8=C(C=C(C=C8C(=O)[C@@]67[C@@H]([C@@H]5O)C(=O)C4=C2O)C)O)O)O)O
ORIGINAL ISOLATION REFERENCE
CITATION Kato A; Ando K; Kodama K; Suzuki S; Suzuki K Production, isolation and purification of antitumor active monoglycerides and other antibiotics from Sepedonium ampullosporum. Studies on antiviral and antitumor antibiotics. IX. Journal of Antibiotics 1969 22 (2) 71-76.
DOI 10.7164/antibiotics.22.71 PMID 5814217
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 Sepedonium MycoBank 74837
SYNTHESES
CITATION 1 Nicolaou KC; Lim YH; Papageorgiou CD; Piper JL Total synthesis of (+)-rugulosin and (+)-2,2'-epi-cytoskyrin A through cascade reactions. Angewandte Chemie International Edition 2005 44 (48) 7917-21. DOI: 10.1002/anie.200503678 PMID: 16342134
CITATION 2 Nicolaou KC; Lim YH; Piper JL; Papageorgiou CD Total syntheses of 2,2'-epi-cytoskyrin A, rugulosin, and the alleged structure of rugulin. Journal of the American Chemical Society 2007 129 (13) 4001-13. DOI: 10.1021/ja0685708 PMID: 17355133
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