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Compounds

COMPOUND NPA007338

STRUCTURE
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PROPERTIES
NPAID NPA007338
CLUSTER ID 3103
NODE ID 2370
NAME Aspergillide B
FORMULA C14H22O4
MOLECULAR WEIGHT (Da) 254.3260
ACCURATE MASS (Da) 254.1518
ORIGIN ORGANISM TYPE Fungus
ORIGIN GENUS Aspergillus
ORIGIN SPECIES ostianus strain 01F313
InChIKey FDJDTDDUDZAAFP-NPZYAQMBSA-N
InChI InChI=1S/C14H22O4/c1-10-5-3-2-4-6-11-7-8-12(15)13(18-11)9-14(16)17-10/h4,6,10-13,15H,2-3,5,7-9H2,1H3/b6-4+/t10-,11-,12-,13-/m0/s1
SMILES C[C@H]1CCC/C=C/[C@H]2CC[C@H](O)[C@H](CC(=O)O1)O2
ORIGINAL ISOLATION REFERENCE
CITATION Kito, Keijiro; Ookura, Ryuhei; Yoshida, Sanae; Namikoshi, Michio; Ooi, Takashi; Kusumi, Takenori New cytotoxic 14-membered macrolides from marine-derived fungus Aspergillus ostianus. Organic Letters 2008 10 (2) 225-228.
DOI 10.1021/ol702598q PMID 18078344
ORIGINAL ISOLATION TAXONOMY
RANK NAME DB LINK NCBI
Domain Eukarya - 2759
Kingdom Fungi MycoBank 4751
Phylum Ascomycota MycoBank 4890
Class Eurotiomycetes MycoBank 147545
Order Eurotiales MycoBank 5042
Family Aspergillaceae MycoBank 1131492
Genus Aspergillus MycoBank 5052
SYNTHESES
CITATION 1 Liu J; Xu K; He J; Zhang L; Pan X; She X Concise total synthesis of (+)-aspergillide B. Journal of Organic Chemistry 2009 74 (14) 5063-6. DOI: 10.1021/jo900820f PMID: 19485348
CITATION 2 Trost BM; Bartlett MJ Transition-metal-catalyzed synthesis of aspergillide B: an alkyne addition strategy. Organic Letters 2012 14 (5) 1322-5. DOI: 10.1021/ol300200m PMID: 22356535
REVISIONS
VERSION SMILES CITATION
Original Isolation C[C@@H]1CCCC=C[C@H]2CC[C@@H]([C@@H](O2)CC(=O)O1)O Kito, Keijiro; Ookura, Ryuhei; Yoshida, Sanae; Namikoshi, Michio; Ooi, Takashi; Kusumi, Takenori New cytotoxic 14-membered macrolides from marine-derived fungus Aspergillus ostianus. Organic Letters 2008 10 (2) 225-228. DOI: 10.1021/ol702598q PMID: 18078344
2 C[C@H]1CCC/C=C/[C@H]2CC[C@H](O)[C@H](CC(=O)O1)O2 Smith, Steven G; Goodman, Jonathan M Assigning stereochemistry to single diastereoisomers by GIAO NMR calculation: the DP4 probability. Journal of the American Chemical Society 2010 132 (37) 12946-59. DOI: 10.1021/ja105035r PMID: 20795713
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