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Compounds

COMPOUND NPA016412

STRUCTURE
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PROPERTIES
NPAID NPA016412
CLUSTER ID 249
NODE ID 228
NAME Myriocin
FORMULA C21H39NO6
MOLECULAR WEIGHT (Da) 401.5440
ACCURATE MASS (Da) 401.2777
ORIGIN ORGANISM TYPE Fungus
ORIGIN GENUS Myriococcum
ORIGIN SPECIES albomyces
InChIKey ZZIKIHCNFWXKDY-FMIVXFBMSA-N
InChI InChI=1S/C21H39NO6/c1-2-3-4-10-13-17(24)14-11-8-6-5-7-9-12-15-18(25)19(26)21(22,16-23)20(27)28/h9,12,18-19,23,25-26H,2-8,10-11,13-16,22H2,1H3,(H,27,28)/b12-9+
SMILES CCCCCCC(=O)CCCCCC/C=C/CC(C(C(CO)(C(=O)O)N)O)O
ORIGINAL ISOLATION REFERENCE
CITATION Kluepfel, D; Bagli, J; Baker, H; Charest, M P; Kudelski, A Myriocin, a new antifungal antibiotic from Myriococcum albomyces Journal of Antibiotics 1972 25 (2) 109-115.
DOI 10.7164/antibiotics.25.109 PMID 5034807
ORIGINAL ISOLATION TAXONOMY
RANK NAME DB LINK NCBI
Domain Eukarya - 2759
Kingdom Fungi MycoBank 4751
Phylum Ascomycota MycoBank 4890
Class Ascomycetes MycoBank -
Genus Myriococcum MycoBank 455372
SYNTHESES
CITATION 1 Yoshikawa M; Yokokawa Y; Okuno Y; Murakami N Total synthesis of a novel immunosuppressant, myriocin (thermozymocidin, ISP-I), and Z-myriocin. Chemical and Pharmaceutical Bulletin 1994 42 (4) 994-6. DOI: 10.1248/cpb.42.994 PMID: 8020136
CITATION 2 Oishi T; Ando K; Chida N Stereoselective total synthesis of (+)-myriocin from D-mannose. Chemical Communications 2001 (19) 1932-3. DOI: 10.1039/b104864n PMID: 12240225
CITATION 3 Jones MC; Marsden SP Total synthesis of the immunosuppressants myriocin and 2-epi-myriocin. Organic Letters 2008 10 (18) 4125-8. DOI: 10.1021/ol801709c PMID: 18722462
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