Compounds
| ID | Spectrum Quality | Annotated Name |
|---|
COMPOUND NPA012954
PROPERTIES
| NPAID | NPA012954 |
|---|---|
| CLUSTER ID | 112 |
| NODE ID | 106 |
| NAME | Platencin |
| FORMULA | C24H27NO6 |
| MOLECULAR WEIGHT (Da) | 425.4810 |
| ACCURATE MASS (Da) | 425.1838 |
| ORIGIN ORGANISM TYPE | Fungus |
| ORIGIN GENUS | Unknown-fungus |
| ORIGIN SPECIES | sp. |
| InChIKey | DWUHGPPFFABTIY-RLWZQHMASA-N |
| InChI | InChI=1S/C24H27NO6/c1-13-12-24-9-5-14(13)11-17(24)23(2,18(27)6-10-24)8-7-19(28)25-20-16(26)4-3-15(21(20)29)22(30)31/h3-4,6,10,14,17,26,29H,1,5,7-9,11-12H2,2H3,(H,25,28)(H,30,31)/t14-,17-,23-,24+/m0/s1 |
| SMILES | C[C@@]1([C@@H]2C[C@@H]3CC[C@]2(CC3=C)C=CC1=O)CCC(=O)NC4=C(C=CC(=C4O)C(=O)O)O |
ORIGINAL ISOLATION REFERENCE
| CITATION | Wang, Jun; Kodali, Srinivas; Lee, Sang Ho; Galgoci, Andrew; Painter, Ronald; Dorso, Karen; Racine, Fred; Motyl, Mary; Hernandez, Lorraine; Tinney, Elizabeth; Colletti, Steven L; Herath, Kithsiri; Cummings, Richard; Salazar, Oscar; González, Ignacio; Basilio, Angela; Vicente, Francisca; Genilloud, Olga; Pelaez, Fernando; Jayasuriya, Hiranthi; Young, Katherine; Cully, Doris F; Singh, Sheo B Discovery of platencin, a dual FabF and FabH inhibitor with in vivo antibiotic properties Proceedings of the National Academy of Sciences of the United States of America 2007 104 (18) 7612-7616. | ||
|---|---|---|---|
| DOI | 10.1073/pnas.0700746104 | PMID | 17456595 |
SYNTHESES
| CITATION 1 | Singh V; Sahu BC; Bansal V; Mobin SM Intramolecular cycloaddition in 6,6-spiroepoxycyclohexa-2,4-dienone: simple aromatics to (+/-)-platencin. Organic & Biomolecular Chemistry 2010 8 (19) 4472-4481. DOI: 10.1039/c004316h PMID: 20683538 | ||
|---|---|---|---|
| CITATION 2 | Hayashida J; Rawal VH Total synthesis of (+/-)-platencin. Angewandte Chemie International Edition 2008 47 (23) 4373-4376. DOI: 10.1002/anie.200800756 PMID: 18454442 | ||
| CITATION 3 | Nicolaou KC; Tria GS; Edmonds DJ Total synthesis of platencin. Angewandte Chemie International Edition 2008 47 (9) 1780-1783. DOI: 10.1002/anie.200800066 PMID: 18246566 | ||
| CITATION 4 | Nicolaou KC; Toh QY; Chen DY An expedient asymmetric synthesis of platencin. Journal of the American Chemical Society 2008 130 (34) 11292-11293. DOI: 10.1021/ja804588r PMID: 18665593 | ||
| CITATION 5 | Austin KA; Banwell MG; Willis AC A formal total synthesis of platencin. Organic Letters 2008 10 (20) 4465-4468. DOI: 10.1021/ol801647h PMID: 18798641 | ||
| CITATION 6 | Tiefenbacher K; Mulzer J A nine-step total synthesis of (-)-platencin. Journal of Organic Chemistry 2009 74 (8) 2937-2941. DOI: 10.1021/jo9001855 PMID: 19260660 | ||
| CITATION 7 | Varseev GN; Maier ME Formal total synthesis of platencin. Angewandte Chemie International Edition 2009 48 (20) 3685-3688. DOI: 10.1002/anie.200900447 PMID: 19353600 | ||
| CITATION 8 | Yoshimitsu T; Nojima S; Hashimoto M; Tanaka T Total synthesis of (±)-platencin. Organic Letters 2011 13 (14) 3698-3701. DOI: 10.1021/ol2013439 PMID: 21688769 | ||
| CITATION 9 | Chang EL; Schwartz BD; Draffan AG; Banwell MG; Willis AC A chemoenzymatic and fully stereocontrolled total synthesis of the antibacterial natural product (-)-platencin. Chemistry – An Asian Journal 2015 10 (2) 427-439. DOI: 10.1002/asia.201403069 PMID: 25393231 | ||
