Compounds
ID | Spectrum Quality | Annotated Name |
---|
COMPOUND NPA007338
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. | ||
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DOI | 10.1021/ol702598q | PMID | 18078344 |
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 | ||
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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 |