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Compounds

COMPOUND NPA017440

STRUCTURE
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PROPERTIES
NPAID NPA017440
CLUSTER ID 2508
NODE ID 1966
NAME Terpestacin
FORMULA C25H38O4
MOLECULAR WEIGHT (Da) 402.5750
ACCURATE MASS (Da) 402.2770
ORIGIN ORGANISM TYPE Fungus
ORIGIN GENUS Arthrinium
ORIGIN SPECIES sp.
InChIKey UTGBBPSEQPITLF-QMDQJFAJSA-N
InChI InChI=1S/C25H38O4/c1-16-7-6-8-17(2)13-14-25(5)20(11-10-18(3)21(27)12-9-16)22(19(4)15-26)23(28)24(25)29/h7,10,13,19-21,26-28H,6,8-9,11-12,14-15H2,1-5H3/b16-7-,17-13-,18-10-/t19-,20-,21+,25+/m1/s1
SMILES C/C/1=C/CC/C(=C\C[C@]2([C@H](C/C=C(\[C@H](CC1)O)/C)C(=C(C2=O)O)[C@H](C)CO)C)/C
ORIGINAL ISOLATION REFERENCE
CITATION Iimura, Seiji; Oka, Masahisa; Narita, Yukio; Konishi, Masataka; Kakisawa, Hiroshi; Gao, Qi; Oki, Toshikazu Terpestacin, a novel syncytium formation inhibitor, isolated from Arthrinium species Tetrahedron Letters 1993 34 (3) 493-496.
DOI 10.1016/0040-4039(93)85110-i PMID -
ORIGINAL ISOLATION TAXONOMY
RANK NAME DB LINK NCBI
Domain Eukarya - 2759
Kingdom Fungi MycoBank 4751
Phylum Ascomycota MycoBank 4890
Class Sordariomycetes MycoBank 147550
Order Xylariales MycoBank 37989
Family Apiosporaceae MycoBank 106263
Genus Arthrinium MycoBank 112177
SYNTHESES
CITATION 1 Tatsuta K; Masuda N The first total synthesis of natural (+)-terpestacin, syncytium formation inhibitor. Journal of Antibiotics 1998 51 (6) 602-6. DOI: 10.7164/antibiotics.51.602 PMID: 9711228
CITATION 2 Berger GO; Tius MA Total synthesis of (+/-)-terpestacin and (+/-)-11-epi-terpestacin. Journal of Organic Chemistry 2007 72 (17) 6473-80. DOI: 10.1021/jo070923d PMID: 17630803
CITATION 3 Jin Y; Qiu FG A convergent stereocontrolled total synthesis of (-)-terpestacin. Organic & Biomolecular Chemistry 2012 10 (28) 5452-5. DOI: 10.1039/c2ob25940k PMID: 22710980
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