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Compounds

COMPOUND NPA009797

STRUCTURE
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PROPERTIES
NPAID NPA009797
CLUSTER ID 701
NODE ID 433
NAME Andrastin C
FORMULA C28H40O6
MOLECULAR WEIGHT (Da) 472.6220
ACCURATE MASS (Da) 472.2825
ORIGIN ORGANISM TYPE Fungus
ORIGIN GENUS Penicillium
ORIGIN SPECIES sp. FO-3929
InChIKey AWMJEDMVXAOTQZ-QUQNHZJXSA-N
InChI InChI=1S/C28H40O6/c1-15-14-19-25(6)12-11-20(34-17(3)29)24(4,5)18(25)10-13-26(19,7)28(23(32)33-9)22(31)16(2)21(30)27(15,28)8/h14,18-20,30H,10-13H2,1-9H3/t18-,19+,20+,25-,26+,27+,28-/m1/s1
SMILES CC1=C[C@H]2[C@@]3(CC[C@@H](C([C@H]3CC[C@@]2([C@]4([C@@]1(C(=C(C4=O)C)O)C)C(=O)OC)C)(C)C)OC(=O)C)C
ORIGINAL ISOLATION REFERENCE
CITATION Uchida, Ryuji; Shiomi, Kazuro; Inokoshi, Junji; Sunazuka, Toshiaki; Tanaka, Haruo; Iwai, Yuzuru; Takayanagi, Hiroaki; Omura, Satoshi Andrastins A∼C, new protein farnesyltransferase inhibitors produced by Penicillium sp. FO-3929: II. Structure elucidation and biosynthesis Journal of Antibiotics 1996 49 (5) 418-424.
DOI 10.7164/antibiotics.49.418 PMID 8682717
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 Okamoto R; Takeda K; Tokuyama H; Ihara M; Toyota M Toward the total synthesis of (±)-andrastin C. Journal of Organic Chemistry 2013 78 (1) 93-103. DOI: 10.1021/jo301948h PMID: 23106671
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