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CHEBI:71508 - fluvirucin A1

ChEBI IDCHEBI:71508
ChEBI Namefluvirucin A1
Stars
ASCII Namefluvirucin A1
DefinitionA lactam that is 4-hydroxyazacyclotetradecan-2-one substituted by an ethyl group at position 11, methyl groups at position 3 and 7 and a 3-amino-3,6-dideoxy-α-L-talopyranosyl moiety at position 4 via a glycosyl linkage (the 3R,4S,7R,11S stereoisomer). It is isolated from the fermentation broth of an unidentified actinomycete species and exhibits potent inhibitory activity against influenza A virus.
Last Modified2 January 2013
Submitternamrata
DownloadsMolfile
FormulaC23H44N2O5
Net Charge0
Average Mass428.614
Monoisotopic Mass428.32502
SMILES[H][C@@]1(O[C@H]2CC[C@H](C)CCC[C@H](CC)CCCNC(=O)[C@@H]2C)O[C@@H](C)[C@@H](O)[C@@H](N)[C@H]1O
InChIInChI=1S/C23H44N2O5/c1-5-17-9-6-8-14(2)11-12-18(15(3)22(28)25-13-7-10-17)30-23-21(27)19(24)20(26)16(4)29-23/h14-21,23,26-27H,5-13,24H2,1-4H3,(H,25,28)/t14-,15-,16+,17+,18+,19-,20-,21-,23+/m1/s1
InChIKeyZRJBXPCQRSLIKK-BDPAYSQHSA-N
Roles Classification
Biological Roles:
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
EC 3.2.1.18 (exo-alpha-sialidase) inhibitor  An antiviral drug targeted at influenza viruses. Its mode of action consists of blocking the function of the viral neuraminidase protein (EC 3.2.1.18), thus preventing the virus from budding from the host cell.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application:
EC 3.2.1.18 (exo-alpha-sialidase) inhibitor  An antiviral drug targeted at influenza viruses. Its mode of action consists of blocking the function of the viral neuraminidase protein (EC 3.2.1.18), thus preventing the virus from budding from the host cell.
ChEBI Ontology
Outgoing Relation(s)
fluvirucin A1 (CHEBI:71508) has role antimicrobial agent (CHEBI:33281)
fluvirucin A1 (CHEBI:71508) has role EC 3.2.1.18 (exo-α-sialidase) inhibitor (CHEBI:52425)
fluvirucin A1 (CHEBI:71508) has role metabolite (CHEBI:25212)
fluvirucin A1 (CHEBI:71508) is a aminoglycoside (CHEBI:47779)
fluvirucin A1 (CHEBI:71508) is a lactam (CHEBI:24995)
fluvirucin A1 (CHEBI:71508) is a macrocycle (CHEBI:51026)
Incoming Relation(s)
N-methylfluvirucin A1 (CHEBI:65750) has functional parent fluvirucin A1 (CHEBI:71508)
6-desmethyl-N-methylfluvirucin A1 (CHEBI:65749) has functional parent fluvirucin A1 (CHEBI:71508)
IUPAC Name 
(3R,4S,7R,11S)-11-ethyl-3,7-dimethyl-2-oxoazacyclotetradecan-4-yl 3-amino-3,6-dideoxy-α-L-talopyranoside
Synonym  Source
(2R,3S,6R,10S)-3-[(3-amino-3,6-dideoxy-α-L-talopyranosyl)-oxy]-2,6-dimethyl-10-ethyl-13-tridecanelactamChEBI
Citations