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CHEBI:65515 - brasilinolide B

ChEBI IDCHEBI:65515
ChEBI Namebrasilinolide B
Stars
DefinitionA 32-membered macrolide antibiotic isolated from the fermentation broth of Nocardia brasiliensis. It exhibits antifungal activity.
Last Modified11 March 2015
DownloadsMolfile
FormulaC59H104O23
Net Charge0
Average Mass1181.458
Monoisotopic Mass1180.69684
SMILES[H][C@]12C[C@@H](O)C[C@H](OC(=O)C(CCCC)C(=O)OC)CCC[C@H](O)[C@]3([H])O[C@@]3([H])[C@H](C)[C@@]([H])([C@@H](C)[C@@H](O)[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)O[C@H]3C[C@H](OC)[C@H](OC)[C@H](C)O3)OC(=O)/C=C/C[C@H](O)C[C@H](O)C[C@@H](O)CC[C@@H](C)[C@H](O)C[C@](O)(O1)[C@H](O)[C@@H](O)C2
InChIInChI=1S/C59H104O23/c1-12-13-18-43(57(71)76-11)58(72)79-41-17-15-19-44(64)55-53(81-55)34(6)52(33(5)51(69)32(4)50(68)31(3)35(7)77-49-28-47(74-9)54(75-10)36(8)78-49)80-48(67)20-14-16-37(60)23-39(62)24-38(61)22-21-30(2)46(66)29-59(73)56(70)45(65)27-42(82-59)26-40(63)25-41/h14,20,30-47,49-56,60-66,68-70,73H,12-13,15-19,21-29H2,1-11H3/b20-14+/t30-,31+,32-,33+,34-,35+,36+,37+,38+,39+,40+,41-,42-,43?,44+,45+,46-,47+,49-,50+,51+,52-,53+,54-,55+,56-,59+/m1/s1
InChIKeyAXFOSMASHUQEMX-QWVZVQMISA-N
Species of MetaboliteComponentSourceComments
Nocardia brasiliensis (ncbitaxon:37326) - PubMed (10724012) Strain: IFM 0466
Roles Classification
Biological Roles:
antifungal agent  An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
ChEBI Ontology
Outgoing Relation(s)
brasilinolide B (CHEBI:65515) has role antifungal agent (CHEBI:35718)
brasilinolide B (CHEBI:65515) has role metabolite (CHEBI:25212)
brasilinolide B (CHEBI:65515) is a deoxy hexoside (CHEBI:35315)
brasilinolide B (CHEBI:65515) is a epoxide (CHEBI:32955)
brasilinolide B (CHEBI:65515) is a macrolide antibiotic (CHEBI:25105)
brasilinolide B (CHEBI:65515) is a methyl ester (CHEBI:25248)
IUPAC Name 
(1R,3R,5R,9S,10S,12S,13R,14R,17E,20S,22R,24S,27R,28R,30S,31R,32S)-14-{(2S,3S,4R,5R,6R,7S)-7-[(2,6-dideoxy-3,4-di-O-methyl-α-L-lyxo-hexopyranosyl)oxy]-3,5-dihydroxy-4,6-dimethyloctan-2-yl}-3,9,20,22,24,28,30,31,32-nonahydroxy-13,27-dimethyl-16-oxo-11,15,34-trioxatricyclo[28.3.1.010,12]tetratriacont-17-en-5-yl methyl butylpropanedioate
Registry NumbersSources
Reaxys:8535952Reaxys
Citations