CHEBI:65459 - australifungin

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ChEBI Name australifungin
ChEBI ID CHEBI:65459
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C23H36O6
Net Charge 0
Average Mass 408.52830
Monoisotopic Mass 408.25119
InChI InChI=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
InChIKey QURROFPXYUFYAZ-GFHGMWMXSA-N
SMILES [H][C@@]12[C@H](O)[C@H](C)C[C@H](O)[C@@]1([H])[C@](C)(C(=O)\C=C/O)C([C@H](C)CCCCCC)=C(O)C2=O
Metabolite of Species Details
Sporormiella australis (NCBI:txid55178) of strain MF5672 See: PubMed
Roles Classification
Biological Role(s): 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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 Number Type Source
7226637 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
10563338 PubMed citation Europe PMC
12684378 PubMed citation Europe PMC
18952903 PubMed citation Europe PMC
22226824 PubMed citation Europe PMC
7797434 PubMed citation Europe PMC
9516416 PubMed citation Europe PMC
Last Modified
16 November 2012