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CHEBI:65459 - australifungin

ChEBI IDCHEBI:65459
ChEBI Nameaustralifungin
Stars
DefinitionA carbobicyclic compound that is 4a,5,6,7,8,8a-hexahydronaphthalen-1(4H)-one substituted by hydroxy groups at positions 2, 5 and 8, a (2Z)-3-hydroxyprop-2-enoyl group at position 4, methyl groups at positions 4 and 7 and a 2R-octan-2-yl group at position 3 (the 4S,4aR,5S,7R,8R,8aS stereoisomer). It is isolated from the fermentation extracts of Sporormiella australis and exhibits antifungal activity by interfering with the fungal lipid metabolism.
Last Modified16 November 2012
DownloadsMolfile
FormulaC23H36O6
Net Charge0
Average Mass408.535
Monoisotopic Mass408.25119
SMILES[H][C@@]12[C@@H](O)C[C@@H](C)[C@@H](O)[C@@]1([H])C(=O)C(O)=C([C@H](C)CCCCCC)[C@@]2(C)C(=O)/C=C\O
InChIInChI=1S/C23H36O6/c1-5-6-7-8-9-13(2)18-22(29)21(28)17-19(15(25)12-14(3)20(17)27)23(18,4)16(26)10-11-24/h10-11,13-15,17,19-20,24-25,27,29H,5-9,12H2,1-4H3/b11-10-/t13-,14-,15+,17+,19-,20-,23-/m1/s1
InChIKeyQURROFPXYUFYAZ-GFHGMWMXSA-N
Species of MetaboliteComponentSourceComments
Sporormiella australis (ncbitaxon:55178) - PubMed (7797434) Strain: MF5672
Roles Classification
Biological Roles:
EC 2.3.1.24 (sphingosine N-acyltransferase) inhibitor  An EC 2.3.1.* (acyltransferase transferring other than amino-acyl group) inhibitor that interferes with the action of sphingosine N-acyltransferase (EC 2.3.1.24).
HIV-1 integrase inhibitor  An inhibitor of HIV-1 integrase, an enzyme required for the integration of the genetic material of the retrovirus into the DNA of the infected cells.
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.
ChEBI Ontology
Outgoing Relation(s)
australifungin (CHEBI:65459) has role antifungal agent (CHEBI:35718)
australifungin (CHEBI:65459) has role EC 2.3.1.24 (sphingosine N-acyltransferase) inhibitor (CHEBI:62530)
australifungin (CHEBI:65459) has role HIV-1 integrase inhibitor (CHEBI:67268)
australifungin (CHEBI:65459) has role metabolite (CHEBI:25212)
australifungin (CHEBI:65459) is a carbobicyclic compound (CHEBI:36785)
australifungin (CHEBI:65459) is a enol (CHEBI:33823)
australifungin (CHEBI:65459) is a enone (CHEBI:51689)
australifungin (CHEBI:65459) is a secondary alcohol (CHEBI:35681)
IUPAC Name 
(4S,4aR,5S,7R,8R,8aS)-2,5,8-trihydroxy-4-[(2Z)-3-hydroxyprop-2-enoyl]-4,7-dimethyl-3-[(2R)-octan-2-yl]-4a,5,6,7,8,8a-hexahydronaphthalen-1(4H)-one
Registry NumbersSources
Reaxys:7226637Reaxys
Citations