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australifungin |
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CHEBI:65459 |
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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. |
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This entity has been manually annotated by the ChEBI Team.
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Molfile
XML
SDF
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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 |
QURROFPXYUFYAZ-GFHGMWMXSA-N |
[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 |
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Sporormiella australis
(NCBI:txid55178)
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of strain
MF5672
See:
PubMed
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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.
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View more via ChEBI Ontology
(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
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7226637
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Reaxys Registry Number
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Reaxys
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10563338
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PubMed citation
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Europe PMC
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12684378
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PubMed citation
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Europe PMC
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18952903
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PubMed citation
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Europe PMC
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22226824
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PubMed citation
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Europe PMC
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7797434
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PubMed citation
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Europe PMC
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9516416
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PubMed citation
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Europe PMC
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