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Compounds

COMPOUND NPA017536

STRUCTURE
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PROPERTIES
NPAID NPA017536
CLUSTER ID 5879
NODE ID 4132
NAME Yaequinolone J2
FORMULA C27H31NO5
MOLECULAR WEIGHT (Da) 449.5470
ACCURATE MASS (Da) 449.2202
ORIGIN ORGANISM TYPE Fungus
ORIGIN GENUS Penicillium
ORIGIN SPECIES sp. FKI-2140
InChIKey CPWPNTRWIIAFEG-STXQHDJLSA-N
InChI InChI=1S/C27H31NO5/c1-17(2)7-6-15-26(3)16-14-18-8-13-21-22(23(18)33-26)27(30,24(32-5)25(29)28-21)19-9-11-20(31-4)12-10-19/h7-14,16,24,30H,6,15H2,1-5H3,(H,28,29)/t24-,26+,27+/m1/s1
SMILES COC1=CC=C([C@]2(O)C3=C(C=CC4=C3O[C@@](C)(CCC=C(C)C)C=C4)NC(=O)[C@H]2OC)C=C1
ORIGINAL ISOLATION REFERENCE
CITATION Uchida, Ryuji; Imasato, Rie; Yamaguchi, Yuichi; Masuma, Rokuro; Shiomi, Kazuro; Tomoda, Hiroshi; Omura, Satoshi Yaequinolones, new insecticidal antibiotics produced by Penicillium sp. FKI-2140: I. Taxonomy, fermentation, isolation and biological activity Journal of Antibiotics 2006 59 (10) 646-651.
DOI 10.1038/ja.2006.86 PMID 17191680
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
REVISIONS
VERSION SMILES CITATION
Original Isolation CC(=CCC[C@@]1(C=CC2=C(O1)C3=C(C=C2)NC(=O)[C@@H]([C@]3(C4=CC=C(C=C4)OC)O)OC)C)C Uchida, Ryuji; Imasato, Rie; Yamaguchi, Yuichi; Masuma, Rokuro; Shiomi, Kazuro; Tomoda, Hiroshi; Omura, Satoshi Yaequinolones, new insecticidal antibiotics produced by Penicillium sp. FKI-2140: I. Taxonomy, fermentation, isolation and biological activity Journal of Antibiotics 2006 59 (10) 646-651. DOI: 10.1038/ja.2006.86 PMID: 17191680
2 COC1=CC=C([C@]2(O)C3=C(C=CC4=C3O[C@@](C)(CCC=C(C)C)C=C4)NC(=O)[C@H]2OC)C=C1 Vece, Vito; Jakkepally, Shashidhar; Hanessian, Stephen Total Synthesis and Absolute Stereochemical Assignment of the Insecticidal Metabolites Yaequinolones J1 and J2. Organic Letters 2018 20 (14) 4277-4280. DOI: 10.1021/acs.orglett.8b01701 PMID: 29975546
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