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Compounds

COMPOUND NPA003916

STRUCTURE
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PROPERTIES
NPAID NPA003916
CLUSTER ID 2105
NODE ID 11
NAME Lapatin B
FORMULA C20H14N4O3
MOLECULAR WEIGHT (Da) 358.3570
ACCURATE MASS (Da) 358.1066
ORIGIN ORGANISM TYPE Fungus
ORIGIN GENUS Penicillium
ORIGIN SPECIES lapatayae IBT 10870
InChIKey RSCQCCZWYNEMPN-VKWYCSODSA-N
InChI InChI=1S/C20H14N4O3/c25-17-14-9-20(11-6-2-4-8-13(11)22-19(20)27)15(23-17)16-21-12-7-3-1-5-10(12)18(26)24(14)16/h1-8,14-15H,9H2,(H,22,27)(H,23,25)/t14-,15+,20?/m0/s1
SMILES C1[C@H]2C(=O)N[C@@H](C13C4=CC=CC=C4NC3=O)C5=NC6=CC=CC=C6C(=O)N25
ORIGINAL ISOLATION REFERENCE
CITATION Larsen, Thomas Ostenfeld; Petersen, Bent O.; Duus, Jens Ø.; Sørensen, Dan; Frisvad, Jens C.; Hansen, Michael E. Discovery of New Natural Products by Application of X-hitting, a Novel Algorithm for Automated Comparison of Full UV Spectra, Combined with Structural Determination by NMR Spectroscopy Journal of Natural Products 2005 68 (6) 871-874.
DOI 10.1021/np040248s PMID 15974610
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 Penicillium MycoBank 5073
SYNTHESES
CITATION 1 Leca D; Gaggini F; Cassayre J; Loiseleur O; Pieniazek SN; Luft JA; Houk KN Acid-catalyzed aza-Diels-Alder reactions for the total synthesis of (+/-)-lapatin B. Journal of Organic Chemistry 2007 72 (11) 4284-7. DOI: 10.1021/jo0705162 PMID: 17480097
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