CHEBI:65515 - brasilinolide B

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ChEBI Name brasilinolide B
ChEBI ID CHEBI:65515
Definition A 32-membered macrolide antibiotic isolated from the fermentation broth of Nocardia brasiliensis. It exhibits antifungal activity.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C59H104O23
Net Charge 0
Average Mass 1181.44330
Monoisotopic Mass 1180.69684
InChI InChI=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
InChIKey AXFOSMASHUQEMX-QWVZVQMISA-N
SMILES [H][C@]12C[C@@H](O)C[C@@H](CCC[C@H](O)[C@]3([H])O[C@@]3([H])[C@H](C)[C@]([H])(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)[C@@H](C)[C@@H](O)[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)O[C@H]1C[C@H](OC)[C@H](OC)[C@H](C)O1)OC(=O)C(CCCC)C(=O)OC
Metabolite of Species Details
Nocardia brasiliensis (NCBI:txid37326) of strain IFM 0466 See: PubMed
Roles Classification
Biological Role(s): 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.
(via macrolide antibiotic )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 Number Type Source
8535952 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
10724012 PubMed citation Europe PMC
Last Modified
11 March 2015