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australifungin
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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03. Biological Effects of Specific Chemicals: antimicrobial agent [CHEBI:33281] > antiviral agent [CHEBI:22587] > anti-HIV agent [CHEBI:64946] > anti-HIV-1 agent [CHEBI:64947] > HIV-1 integrase inhibitor [CHEBI:67268]
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03. Biological Effects of Specific Chemicals 
03. Biological Effects of Specific Chemicals
 biochemical uses [CHEBI:52206] (3306) 
 enzyme inhibitor [CHEBI:23924] (825) 
 sphingosine N-acyltransferase inhibitor [CHEBI:62530] (1) 
 australifungin [CHEBI:65459] (1)
 metabolite [CHEBI:25212] (2692) 
 secondary metabolite [CHEBI:26619] (2225) 
 australifungin [CHEBI:65459] (1)
 antimicrobial agent [CHEBI:33281] (927) 
 antiviral agent [CHEBI:22587] (216) 
 anti-HIV agent [CHEBI:64946] (126) 
 anti-HIV-1 agent [CHEBI:64947] (79) 
 HIV-1 integrase inhibitor [CHEBI:67268] (16) 
 australifungin [CHEBI:65459] (1)
 antifungal agent [CHEBI:35718] (130) 
 australifungin [CHEBI:65459] (1)
08. Chemical Category 
08. Chemical Category
 main group molecular entity [CHEBI:33579] (25650) 
 s-block molecular entity [CHEBI:33674] (7287) 
 hydrogen molecular entity [CHEBI:33608] (6932) 
 hydroxides [CHEBI:24651] (5641) 
 organic hydroxy compound [CHEBI:33822] (3050) 
 alcohol [CHEBI:30879] (1371) 
 secondary alcohol [CHEBI:35681] (342) 
 australifungin [CHEBI:65459] (1)
 enol [CHEBI:33823] (52) 
 australifungin [CHEBI:65459] (1)
 p-block molecular entity [CHEBI:33675] (25343) 
 chalcogen molecular entity [CHEBI:33304] (15225) 
 oxygen molecular entity [CHEBI:25806] (14414) 
 hydroxides [CHEBI:24651] (5641) 
 organic hydroxy compound [CHEBI:33822] (3050) 
 alcohol [CHEBI:30879] (1371) 
 secondary alcohol [CHEBI:35681] (342) 
 australifungin [CHEBI:65459] (1)
 enol [CHEBI:33823] (52) 
 australifungin [CHEBI:65459] (1)
 organooxygen compound [CHEBI:36963] (11352) 
 carbonyl compound [CHEBI:36586] (5928) 
 ketone [CHEBI:17087] (1288) 
 alpha,beta-unsaturated ketone [CHEBI:51721] (238) 
 enone [CHEBI:51689] (233) 
 australifungin [CHEBI:65459] (1)
 organochalcogen compound [CHEBI:36962] (11874) 
 organooxygen compound [CHEBI:36963] (11352) 
 carbonyl compound [CHEBI:36586] (5928) 
 ketone [CHEBI:17087] (1288) 
 alpha,beta-unsaturated ketone [CHEBI:51721] (238) 
 enone [CHEBI:51689] (233) 
 australifungin [CHEBI:65459] (1)
 carbon group molecular entity [CHEBI:33582] (23847) 
 organic molecular entity [CHEBI:50860] (23769) 
 heteroorganic entity [CHEBI:33285] (15197) 
 organochalcogen compound [CHEBI:36962] (11874) 
 organooxygen compound [CHEBI:36963] (11352) 
 carbonyl compound [CHEBI:36586] (5928) 
 ketone [CHEBI:17087] (1288) 
 alpha,beta-unsaturated ketone [CHEBI:51721] (238) 
 enone [CHEBI:51689] (233) 
 australifungin [CHEBI:65459] (1)
 organic hydroxy compound [CHEBI:33822] (3050) 
 alcohol [CHEBI:30879] (1371) 
 secondary alcohol [CHEBI:35681] (342) 
 australifungin [CHEBI:65459] (1)
 enol [CHEBI:33823] (52) 
 australifungin [CHEBI:65459] (1)
 organic molecule [CHEBI:72695] (11399) 
 organic cyclic compound [CHEBI:33832] (7633) 
 carbocyclic compound [CHEBI:33598] (1130) 
 carbopolycyclic compound [CHEBI:35294] (493) 
 carbobicyclic compound [CHEBI:36785] (199) 
 australifungin [CHEBI:65459] (1)
 organic oxo compound [CHEBI:36587] (5932) 
 carbonyl compound [CHEBI:36586] (5928) 
 ketone [CHEBI:17087] (1288) 
 alpha,beta-unsaturated ketone [CHEBI:51721] (238) 
 enone [CHEBI:51689] (233) 
 australifungin [CHEBI:65459] (1)
 polyatomic entity [CHEBI:36357] (18777) 
 molecule [CHEBI:25367] (11520) 
 cyclic compound [CHEBI:33595] (7817) 
 homocyclic compound [CHEBI:33597] (1134) 
 carbocyclic compound [CHEBI:33598] (1130) 
 carbopolycyclic compound [CHEBI:35294] (493) 
 carbobicyclic compound [CHEBI:36785] (199) 
 australifungin [CHEBI:65459] (1)
 homopolycyclic compound [CHEBI:35295] (493) 
 carbopolycyclic compound [CHEBI:35294] (493) 
 carbobicyclic compound [CHEBI:36785] (199) 
 australifungin [CHEBI:65459] (1)
 polycyclic compound [CHEBI:33635] (4078) 
 homopolycyclic compound [CHEBI:35295] (493) 
 carbopolycyclic compound [CHEBI:35294] (493) 
 carbobicyclic compound [CHEBI:36785] (199) 
 australifungin [CHEBI:65459] (1)
 bicyclic compound [CHEBI:33636] (1511) 
 carbobicyclic compound [CHEBI:36785] (199) 
 australifungin [CHEBI:65459] (1)
 organic cyclic compound [CHEBI:33832] (7633) 
 carbocyclic compound [CHEBI:33598] (1130) 
 carbopolycyclic compound [CHEBI:35294] (493) 
 carbobicyclic compound [CHEBI:36785] (199) 
 australifungin [CHEBI:65459] (1)
 organic molecule [CHEBI:72695] (11399) 
 organic cyclic compound [CHEBI:33832] (7633) 
 carbocyclic compound [CHEBI:33598] (1130) 
 carbopolycyclic compound [CHEBI:35294] (493) 
 carbobicyclic compound [CHEBI:36785] (199) 
 australifungin [CHEBI:65459] (1)
 organic oxo compound [CHEBI:36587] (5932) 
 carbonyl compound [CHEBI:36586] (5928) 
 ketone [CHEBI:17087] (1288) 
 alpha,beta-unsaturated ketone [CHEBI:51721] (238) 
 enone [CHEBI:51689] (233) 
 australifungin [CHEBI:65459] (1)
 heteroatomic molecular entity [CHEBI:37577] (13672) 
 hydroxides [CHEBI:24651] (5641) 
 organic hydroxy compound [CHEBI:33822] (3050) 
 alcohol [CHEBI:30879] (1371) 
 secondary alcohol [CHEBI:35681] (342) 
 australifungin [CHEBI:65459] (1)
 enol [CHEBI:33823] (52) 
 australifungin [CHEBI:65459] (1)
ChEBI Compound Accession Identifier:   [CHEBI:65459]
ChEBI Compound Description:   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.
ChEBI Compound Identification Number:   65459
ChEBI InChI Value:   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
ChEBI InChIKey Value:   QURROFPXYUFYAZ-GFHGMWMXSA-N
ChEBI Compound Name:   australifungin
ChEBI SMILES Value:   [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
ChEBI Substance ID:   160644929
ChEBI URL:   ChEBI:65459
ChemSpider ID:   4440358
Ontomatica Chemical Accession Key (OnChAKey):   QURROFPXYUFYAZ_GFHGMWMXSA_N_000_000000
PubChem Compound ID:   5276375