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1-phosphatidyl-1D-myo-inositol + 6-((N-(7-nitrobenz-2-oxa-1,3-diazol-4-yl)amino)-hexanoyl)-sphingosine
?
1-phosphatidyl-1D-myo-inositol + C6-N-(7-nitrobenz-2-oxa-1,3-diazol-4-yl)ceramide
?
-
-
-
?
1-phosphatidyl-1D-myo-inositol + hydroxy fatty acid-containing ceramide
hydroxy fatty acid-containing inositolphosphoylceramide
-
-
-
-
?
1-phosphatidyl-1D-myo-inositol + N-[(2R,4E)-1-hydroxyoctadec-4-en-2-yl]octanamide
1,2-diacyl-sn-glycerol + ?
-
-
-
?
1-phosphatidyl-1D-myo-inositol + N-[6-[(7-nitro-2-1,3-benzoxadiazol-4-yl)amino]hexanoyl]-D-erythro-sphingosine
?
1-phosphatidyl-1D-myo-inositol + nonhydroxy fatty acid-containing ceramide
nonhydroxy fatty acid-containing inositolphosphoylceramide
-
-
-
-
?
L-alpha-phosphatidylinositol + C6-NBD-ceramide
?
-
-
-
?
additional information
?
-
1-phosphatidyl-1D-myo-inositol + 6-((N-(7-nitrobenz-2-oxa-1,3-diazol-4-yl)amino)-hexanoyl)-sphingosine
?
-
-
-
?
1-phosphatidyl-1D-myo-inositol + 6-((N-(7-nitrobenz-2-oxa-1,3-diazol-4-yl)amino)-hexanoyl)-sphingosine
?
-
-
-
-
?
1-phosphatidyl-1D-myo-inositol + 6-((N-(7-nitrobenz-2-oxa-1,3-diazol-4-yl)amino)-hexanoyl)-sphingosine
?
-
-
-
?
1-phosphatidyl-1D-myo-inositol + 6-((N-(7-nitrobenz-2-oxa-1,3-diazol-4-yl)amino)-hexanoyl)-sphingosine
?
-
-
-
-
?
1-phosphatidyl-1D-myo-inositol + 6-((N-(7-nitrobenz-2-oxa-1,3-diazol-4-yl)amino)-hexanoyl)-sphingosine
?
-
-
-
?
1-phosphatidyl-1D-myo-inositol + N-[6-[(7-nitro-2-1,3-benzoxadiazol-4-yl)amino]hexanoyl]-D-erythro-sphingosine
?
-
-
-
-
?
1-phosphatidyl-1D-myo-inositol + N-[6-[(7-nitro-2-1,3-benzoxadiazol-4-yl)amino]hexanoyl]-D-erythro-sphingosine
?
-
-
-
-
?
1-phosphatidyl-1D-myo-inositol + N-[6-[(7-nitro-2-1,3-benzoxadiazol-4-yl)amino]hexanoyl]-D-erythro-sphingosine
?
-
-
-
-
?
1-phosphatidyl-1D-myo-inositol + N-[6-[(7-nitro-2-1,3-benzoxadiazol-4-yl)amino]hexanoyl]-D-erythro-sphingosine
?
-
-
-
-
?
1-phosphatidyl-1D-myo-inositol + N-[6-[(7-nitro-2-1,3-benzoxadiazol-4-yl)amino]hexanoyl]-D-erythro-sphingosine
?
-
-
-
-
?
1-phosphatidyl-1D-myo-inositol + N-[6-[(7-nitro-2-1,3-benzoxadiazol-4-yl)amino]hexanoyl]-D-erythro-sphingosine
?
-
-
-
-
?
1-phosphatidyl-1D-myo-inositol + N-[6-[(7-nitro-2-1,3-benzoxadiazol-4-yl)amino]hexanoyl]-D-erythro-sphingosine
?
-
-
-
-
?
1-phosphatidyl-1D-myo-inositol + N-[6-[(7-nitro-2-1,3-benzoxadiazol-4-yl)amino]hexanoyl]-D-erythro-sphingosine
?
-
-
-
-
?
additional information
?
-
synthesis of ceramide derivatives built around a set of hydroxybutenyl amine cores, exploring variations in the sphingosine tail, N-acyl unit and the degree of hydroxylation. The C-3 hydroxyl group is not essential for turnover but it provides enhanced affinity. A long (C13) hydrocarbon ceramide tail is necessary for both high affinity and turnover. The N-acyl chain also contributes to affinity, analogues lacking the amide linkage function as competitive inhibitors in both enzyme and cell-based assays
-
-
?
additional information
?
-
-
synthesis of ceramide derivatives built around a set of hydroxybutenyl amine cores, exploring variations in the sphingosine tail, N-acyl unit and the degree of hydroxylation. The C-3 hydroxyl group is not essential for turnover but it provides enhanced affinity. A long (C13) hydrocarbon ceramide tail is necessary for both high affinity and turnover. The N-acyl chain also contributes to affinity, analogues lacking the amide linkage function as competitive inhibitors in both enzyme and cell-based assays
-
-
?
additional information
?
-
-
maximum product formation is observed at 1-phosphatidyl-1D-myo-inositol concentrations in excess of 600 microM
-
-
?
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(1R)-1-cyclohexyl-5-(3,4-dimethoxyphenyl)-3-methyl-2-oxopentyl 3-hydroxy-N-methyl-N-(2-propylpentanoyl)valinate
synthetic inhibitor based on aureobasdidin A structure, reversible
(1R)-1-cyclohexyl-5-(3,4-dimethoxyphenyl)-3-methyl-2-oxopentyl 3-hydroxy-N-methyl-N-(6-phenylhexanoyl)valinate
synthetic inhibitor based on aureobasdidin A structure, reversible
(1R)-1-cyclohexyl-5-(3,4-dimethoxyphenyl)-3-methyl-2-oxopentyl 3-hydroxy-N-methyl-N-nonanoylvalinate
synthetic inhibitor based on aureobasdidin A structure, reversible
(2R,4E)-2-aminooctadec-4-en-1-ol
compound displays significant anti-protozoal effects at the concentrations analyzed
1-phosphatidyl-1D-myo-inositol
substrate inhibition
3-(1,3-benzodioxol-5-yl)-6-[[(1E)-1H-pyrrol-2-ylmethylene]amino]-2H-chromene-2-one
-
coumarin derivative. Molecular dynamics modeling, free energy of binding is -9.5 kcal/mol
3-(2H-1,3-benzodioxol-5-yl)-6-[(E)-[(furan-2-yl)methylidene]amino]-2H-1-benzopyran-2-one
-
coumarin derivative with little cytotoxic effects.Molecular dynamics modeling, free energy of binding is -9.8 kcal/mol
3-[(4-fluorophenyl)methyl]-7-(1H-pyrrole-1-sulfonyl)-2,3,4,5-tetrahydro-1H-3-benzazepine
selective, non-toxic benzazepane inhibitor, inhibits the enzyme at nanomolar concentrations
4-(2,5-dimethyl-4-[(E)-[(piperidin-1-yl)methylidene]amino]phenoxy)-2-(2,2-dimethylpropyl)benzonitrile
inhibitor shows selectivity for isoform IPCS2 over the yeast orthologue, and activity against Arabidopsis thaliana seedlings
7-(4-fluoro-1H-indole-1-sulfonyl)-3-[(pyridin-3-yl)methyl]-2,3,4,5-tetrahydro-1H-3-benzazepine
selective, non-toxic benzazepane inhibitor, inhibits the enzyme at nanomolar concentrations
amidosulfobetaine-16
inactivates the enzyme irreversibly
Brij
inactivates the enzyme
-
CHAPS
-
0.1% w/v, 44% loss of activity
Empigen BB
inactivates the enzyme irreversibly
Mn2+
-
5 mM, 80% loss of activity
N-dodecyl-N,N-(dimethylammonio)butanoate
inactivates the enzyme irreversibly
N-[(2R,4E)-1-hydroxyoctadec-4-en-2-yl]-2-phenylacetamide
-
N-[(2S,4E)-3-hydroxyoctadec-4-en-2-yl]octanamide
-
Nonidet P-40
inactivates the enzyme
taurocholic acid
-
0.1% w/v, 70% loss of activity
Tween 80
inactivates the enzyme
Zwittergent 3-10
inactivates the enzyme irreversibly
-
aureobasidin A
-
IC50 value 2.6 ng/ml. Strain is intrinsically resistant to aureobasidin A (MIC above 50 microg/ml), but has IPC synthase activity sensitive to aureobasidin A
aureobasidin A
-
strongly inhibits the activity of IPC synthase in wild-type, which leads to distinct changes in cell morphology, including the delay in conidial germination, excessive branching near the tip of the germ tube and mycelium, and the inhibition of the mycelium growth. Aureobasidin A prevents the infection of wild-type in tomato fruits via reducing oxalic acid secretion and the activity of cellulase and pectinase
aureobasidin A
-
IC50 value 2.1 ng/ml. All Candida species tested are well susceptible to aureobasidin A with MICs below 2 microg/ml
aureobasidin A
irreversible
aureobasidin A
-
IC50 value 3.4 ng/ml. All Candida species tested are well susceptible to aureobasidin A with MICs below 2 microg/ml
aureobasidin A
enzyme is inhibited at concentrations of 0.1 microM
aureobasidin A
irreversible
aureobasidin A
-
inhibits Aur1, activates vacuolar acidification and strongly induces the cell wall integrity pathway
aureobasidin A
potent inhibitor
aureobasidin A
-
IC50 value 2.5 ng/ml. All Candida species tested are well susceptible to aureobasidin A with MICs below 2 microg/ml
haplofungin A
-
isolated from Lauriomyces bellulus SANK 26899, inhibits the activity of IPC synthase with an IC50 value of 0.25 microg/ml and suppresses the growth of Candida glabrata at the MIC value of 0.5 microg/ml
haplofungin A
-
isolated from Lauriomyces bellulus SANK 26899, inhibits the activity of IPC synthase with an IC50 value of 0.0015 microg/ml and also suppresses the growth of Candida glabrata at the MIC value of 0.5 microg/ml
haplofungin E
-
isolated from Lauriomyces bellulus SANK 26899, inhibits the activity of IPC synthase with an IC50 value of 0.24 microg/ml and suppresses the growth of Candida glabrata at the MIC value of 0.5 microg/ml
haplofungin E
-
isolated from Lauriomyces bellulus SANK 26899, inhibits the activity of IPC synthase with an IC50 value of 0.0015 microg/ml and also suppresses the growth of Candida glabrata at the MIC value of 0.5 microg/ml
khafrefungin
-
octylglucoside
inactivates the enzyme
octylglucoside
-
0.1% w/v, 40% loss of activity
rustimicin
i.e. galbonolide A
rustimicin
i.e. galbonolide A
Triton X-100
inactivates the enzyme
Triton X-100
-
0.1% w/v, 75% loss of activity
Tween 20
inactivates the enzyme
Tween 20
-
0.1% w/v, 55% loss of activity
additional information
isoform IPCS1 is insensitive to the addition of aureobasidin A at 0.005 mM; isoform IPCS1 is insensitive to the addition of aureobasidin A at 0.005 mM; isoform IPCS1 is insensitive to the addition of aureobasidin A at 0.005 mM
-
additional information
isoform IPCS1 is insensitive to the addition of aureobasidin A at 0.005 mM; isoform IPCS1 is insensitive to the addition of aureobasidin A at 0.005 mM; isoform IPCS1 is insensitive to the addition of aureobasidin A at 0.005 mM
-
additional information
isoform IPCS1 is insensitive to the addition of aureobasidin A at 0.005 mM; isoform IPCS1 is insensitive to the addition of aureobasidin A at 0.005 mM; isoform IPCS1 is insensitive to the addition of aureobasidin A at 0.005 mM
-
additional information
synthesis of ceramide derivatives built around a set of hydroxybutenyl amine cores, exploring variations in the sphingosine tail, N-acyl unit and the degree of hydroxylation. The N-acyl chain contributes to affinity, analogues lacking the amide linkage function as competitive inhibitors in both enzyme and cell-based assays
-
additional information
-
synthesis of ceramide derivatives built around a set of hydroxybutenyl amine cores, exploring variations in the sphingosine tail, N-acyl unit and the degree of hydroxylation. The N-acyl chain contributes to affinity, analogues lacking the amide linkage function as competitive inhibitors in both enzyme and cell-based assays
-
additional information
-
neither activating nor inhibitory: 1mM ATP or GTP, 5 mM Ca2+ or Mg2+, 100 mM KCl
-
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Zhong, W.; Jeffries, M.W.; Georgopapadakou, N.H.
Inhibition of inositol phosphorylceramide synthase by aureobasidin A in Candida and Aspergillus species
Antimicrob. Agents Chemother.
44
651-653
2000
Aspergillus flavus, Candida albicans, [Candida] glabrata, Candida tropicalis, [Candida] glabrata ATCC 90030, Candida tropicalis ATCC 750, Aspergillus flavus ATCC 9643, Candida albicans ATCC 90028
brenda
Aeed, P.A.; Young, C.L.; Nagiec, M.M.; Elhammer, A.P.
Inhibition of inositol phosphorylceramide synthase by the cyclic peptide aureobasidin A
Antimicrob. Agents Chemother.
53
496-504
2009
Candida albicans (O13332), Candida albicans, Saccharomyces cerevisiae (P36107), Saccharomyces cerevisiae, Candida albicans ATCC MYA-2876 (O13332)
brenda
Bromley, P.; Li, Y.; Murphy, S.; Sumner, C.; Lynch, D.
Complex sphingolipid synthesis in plants Characterization of inositolphosphorylceramide synthase activity in bean microsomes
Arch. Biochem. Biophys.
417
219-226
2003
Phaseolus vulgaris
brenda
Aeed, P.A.; Sperry, A.E.; Young, C.L.; Nagiec, M.M.; Elhammer, A.P.
Effect of membrane perturbants on the activity and phase distribution of inositol phosphorylceramide synthase; development of a novel assay
Biochemistry
43
8483-8493
2004
Candida albicans (O13332), Candida albicans, Candida albicans ATCC MYA-2876 (O13332)
brenda
Voynova, N.; Roubaty, C.; Vazquez, H.; Mallela, S.; Ejsing, C.; Conzelmann, A.
Saccharomyces cerevisiae is dependent on vesicular traffic between the Golgi apparatus and the vacuole when inositolphosphorylceramide synthase aur1 is inactivated
Eukaryot. Cell
14
1203-1216
2015
Saccharomyces cerevisiae
brenda
Mandlik, V.; Singh, S.
Molecular docking and molecular dynamics simulation study of inositol phosphorylceramide synthase - inhibitor complex in leishmaniasis Insight into the structure based drug design
F1000Res.
5
1610
2016
Leishmania major
brenda
Ohnuki, T.; Yano, T.; Ono, Y.; Kozuma, S.; Suzuki, T.; Ogawa, Y.; Takatsu, T.
Haplofungins, novel inositol phosphorylceramide synthase inhibitors, from Lauriomyces bellulus SANK 26899 I. Taxonomy, fermentation, isolation and biological activities
J. Antibiot.
62
545-549
2009
Aspergillus fumigatus, Saccharomyces cerevisiae
brenda
Nagiec, M.M.; Nagiec, E.E.; Baltisberger, J.A.; Wells, G.B.; Lester, R.L.; Dickson, R.C.
Sphingolipid synthesis as a target for antifungal drugs. Complementation of the inositol phosphorylceramide synthase defect in a mutant strain of Saccharomyces cerevisiae by the AUR1 gene
J. Biol. Chem.
272
9809-9817
1997
Saccharomyces cerevisiae (P36107), Saccharomyces cerevisiae
brenda
Denny, P.W.; Shams-Eldin, H.; Price, H.P.; Smith, D.F.; Schwarz, R.T.
The protozoan inositol phosphorylceramide synthase a novel drug target that defines a new class of sphingolipid synthase
J. Biol. Chem.
281
28200-28209
2006
Leishmania major (E9AFX2)
brenda
Wang, X.H.; Guo, X.J.; Li, H.Y.; Gou, P.
Characteristics of inositol phosphorylceramide synthase and effects of aureobasidin A on growth and pathogenicity of Botrytis cinerea
J. Gen. Appl. Microbiol.
61
108-116
2015
Botrytis cinerea
brenda
Yoo, B.; Kim, M.
Isolation of the inositol phosphoceramide synthase gene (AUR1) from stress-tolerant yeast Pichia kudriavzevii
J. Microbiol. Biotechnol.
25
1902-1907
2015
Pichia kudriavzevii (A0A099NZ49)
brenda
Levine, T.P.; Wiggins, C.A.; Munro, S.
Inositol phosphorylceramide synthase is located in the Golgi apparatus of Saccharomyces cerevisiae
Mol. Biol. Cell
11
2267-2281
2000
Saccharomyces cerevisiae (P36107), Saccharomyces cerevisiae
brenda
Sato, K.; Noda, Y.; Yoda, K.
Kei1 a novel subunit of inositolphosphorylceramide synthase, essential for its enzyme activity and Golgi localization
Mol. Biol. Cell
20
4444-4457
2009
Saccharomyces cerevisiae (Q06346 and P36107), Saccharomyces cerevisiae
brenda
Mina, J.G.; Mosely, J.A.; Ali, H.Z.; Denny, P.W.; Steel, P.G.
Exploring Leishmania major inositol phosphorylceramide synthase (LmjIPCS) insights into the ceramide binding domain
Org. Biomol. Chem.
9
1823-1830
2011
Leishmania major (E9AFX2), Leishmania major
brenda
Mina, J.G.; Okada, Y.; Wansadhipathi-Kannangara, N.K.; Pratt, S.; Shams-Eldin, H.; Schwarz, R.T.; Steel, P.G.; Fawcett, T.; Denny, P.W.
Functional analyses of differentially expressed isoforms of the Arabidopsis inositol phosphorylceramide synthase
Plant Mol. Biol.
73
399-407
2010
Arabidopsis thaliana (Q56Y01), Arabidopsis thaliana (Q9M325), Arabidopsis thaliana (Q9SH93)
brenda
Pinneh, E.; Stoppel, R.; Knight, H.; Knight, M.; Steel, P.; DennyI, P.
Expression levels of inositol phosphorylceramide synthase modulate plant responses to biotic and abiotic stress in Arabidopsis thaliana
PLoS ONE
14
e0217087
2019
Arabidopsis thaliana (Q56Y01), Arabidopsis thaliana (Q9M325), Arabidopsis thaliana (Q9SH93), Arabidopsis thaliana
brenda
Norcliffe, J.; Mina, J.; Alvarez, E.; Cantizani, J.; De Dios-Anton, F.; Colmenarejo, G.; Valle, S.; Marco, M.; Fiandor, J.; Martin, J.; Steel, P.; Denny, P.
Identifying inhibitors of the Leishmania inositol phosphorylceramide synthase with antiprotozoal activity using a yeast-based assay and ultra-high throughput screening platform
Sci. Rep.
8
8938
2018
Leishmania major (E9AFX2)
brenda
Pinneh, E.C.; Mina, J.G.; Stark, M.J.R.; Lindell, S.D.; Luemmen, P.; Knight, M.R.; Steel, P.G.; Denny, P.W.
The identification of small molecule inhibitors of the plant inositol phosphorylceramide synthase which demonstrate herbicidal activity
Sci. Rep.
9
8083
2019
Arabidopsis thaliana (Q9SH93)
brenda