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CHEBI:65514 - brasilinolide A

ChEBI IDCHEBI:65514
ChEBI Namebrasilinolide A
Stars
DefinitionA 32-membered macrolide antibiotic isolated from the fermentation broth of Nocardia brasiliensis. It exhibits antifungal and immunosuppressive activity.
Last Modified26 November 2012
DownloadsMolfile
FormulaC57H98O24
Net Charge0
Average Mass1167.387
Monoisotopic Mass1166.64480
SMILES[H][C@]12C[C@@H](O)C[C@H](OC(=O)CC(=O)O)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(=O)CCCC)[C@H](O)[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/C57H98O24/c1-9-10-16-46(67)78-44-25-49(76-34(8)52(44)72)75-33(7)29(3)50(70)30(4)51(71)31(5)53-32(6)54-55(80-54)41(62)15-12-14-39(77-48(69)26-45(65)66)22-38(61)23-40-24-42(63)56(73)57(74,81-40)27-43(64)28(2)18-19-36(59)21-37(60)20-35(58)13-11-17-47(68)79-53/h11,17,28-44,49-56,58-64,70-74H,9-10,12-16,18-27H2,1-8H3,(H,65,66)/b17-11+/t28-,29+,30-,31+,32-,33+,34+,35+,36+,37+,38+,39-,40-,41+,42+,43-,44+,49-,50+,51+,52-,53-,54+,55+,56-,57+/m1/s1
InChIKeyMVSIZSYJQDRVAV-XMTLADTRSA-N
Species of MetaboliteComponentSourceComments
Nocardia brasiliensis (ncbitaxon:37326) - PubMed (9510911) Strain: IFM 0466
Roles Classification
Biological Roles:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
antifungal agent  An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
immunosuppressive agent  An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response.
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
Application:
immunosuppressive agent  An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response.
ChEBI Ontology
Outgoing Relation(s)
brasilinolide A (CHEBI:65514) has role antifungal agent (CHEBI:35718)
brasilinolide A (CHEBI:65514) has role immunosuppressive agent (CHEBI:35705)
brasilinolide A (CHEBI:65514) has role metabolite (CHEBI:25212)
brasilinolide A (CHEBI:65514) is a deoxy hexoside (CHEBI:35315)
brasilinolide A (CHEBI:65514) is a epoxide (CHEBI:32955)
brasilinolide A (CHEBI:65514) is a macrolide antibiotic (CHEBI:25105)
brasilinolide A (CHEBI:65514) is a malonate ester (CHEBI:38083)
IUPAC Name 
3-{[(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-O-pentanoyl-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]oxy}-3-oxopropanoic acid
Registry NumbersSources
Reaxys:8184998Reaxys
CAS:179041-27-1ChemIDplus
Citations