CHEBI:65514 - brasilinolide A

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ChEBI Name brasilinolide A
ChEBI ID CHEBI:65514
Definition A 32-membered macrolide antibiotic isolated from the fermentation broth of Nocardia brasiliensis. It exhibits antifungal and immunosuppressive activity.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C57H98O24
Net Charge 0
Average Mass 1167.37360
Monoisotopic Mass 1166.64480
InChI InChI=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
InChIKey MVSIZSYJQDRVAV-XMTLADTRSA-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(=O)CCCC)[C@H](O)[C@H](C)O1)OC(=O)CC(O)=O
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.
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.
(via macrolide antibiotic )
Application(s): 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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 Numbers Types Sources
179041-27-1 CAS Registry Number ChemIDplus
8184998 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
14987008 PubMed citation Europe PMC
9510911 PubMed citation Europe PMC
Last Modified
26 November 2012