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Information on EC 2.7.1.227 - inositol phosphorylceramide synthase
for references in articles please use BRENDA:EC2.7.1.227
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EC Tree 2 Transferases
2.7 Transferring phosphorus-containing groups
2.7.1 Phosphotransferases with an alcohol group as acceptor
2.7.1.227 inositol phosphorylceramide synthase
IUBMB Comments
The enzyme, characterized from yeast, attaches a phosphoinositol headgroup to α-hydroxyphytoceramides, generating a very-long-chain inositol phospho-α hydroxyphytoceramide (IPC), the simplest of the three complex sphingolipids produced by yeast.
The enzyme appears in viruses and cellular organisms
- 2.7.1.227
- sphingolipids
-
aureobasidin
-
protozoan
- leishmania
- sphingomyelin
- leishmaniasis
- palmitoyltransferase
-
anti-fungal
-
inositolphosphorylceramide
-
anti-protozoal
- neoformans
- kinetoplastids
-
depsipeptide
- phytosphingosine
-
phosphosphingolipid
- analysis
Reaction Schemes
show+
=
+
+
a very-long-chain (2'R)-2'-hydroxyphytoceramide
=
+
a very-long-chain inositol phospho-(2'R)-2'-hydroxyphytoceramide
Synonyms
ipc synthase, inositol phosphorylceramide synthase, at2g37940, more
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
AUR1
IPC synthase
KEI1
AUR1
-
-
-
-
KEI1
-
-
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
1-phosphatidyl-1D-myo-inositol + a very-long-chain (2'R)-2'-hydroxyphytoceramide = 1,2-diacyl-sn-glycerol + a very-long-chain inositol phospho-(2'R)-2'-hydroxyphytoceramide
-
-
-
-
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PATHWAY SOURCE
PATHWAYS
MetaCyc
sphingolipid biosynthesis (yeast)
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SYSTEMATIC NAME
IUBMB Comments
1-phosphatidyl-1D-myo-inositol:(2'R)-2'-hydroxy-phytoceramide phosphoinositoltransferase
The enzyme, characterized from yeast, attaches a phosphoinositol headgroup to alpha-hydroxyphytoceramides, generating a very-long-chain inositol phospho-alpha hydroxyphytoceramide (IPC), the simplest of the three complex sphingolipids produced by yeast.
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
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
?
Substrates: -
Products: -
Products: -
?
1-phosphatidyl-1D-myo-inositol + hydroxy fatty acid-containing ceramide
hydroxy fatty acid-containing inositolphosphoylceramide
-
Substrates: -
Products: -
Products: -
?
1-phosphatidyl-1D-myo-inositol + N-[(2R,4E)-1-hydroxyoctadec-4-en-2-yl]octanamide
1,2-diacyl-sn-glycerol + ?
Substrates: -
Products: -
Products: -
?
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
-
Substrates: -
Products: -
Products: -
?
1-phosphatidyl-1D-myo-inositol + 6-((N-(7-nitrobenz-2-oxa-1,3-diazol-4-yl)amino)-hexanoyl)-sphingosine
?
Substrates: -
Products: -
Products: -
?
1-phosphatidyl-1D-myo-inositol + 6-((N-(7-nitrobenz-2-oxa-1,3-diazol-4-yl)amino)-hexanoyl)-sphingosine
?
-
Substrates: -
Products: -
Products: -
?
1-phosphatidyl-1D-myo-inositol + 6-((N-(7-nitrobenz-2-oxa-1,3-diazol-4-yl)amino)-hexanoyl)-sphingosine
?
Substrates: -
Products: -
Products: -
?
1-phosphatidyl-1D-myo-inositol + 6-((N-(7-nitrobenz-2-oxa-1,3-diazol-4-yl)amino)-hexanoyl)-sphingosine
?
-
Substrates: -
Products: -
Products: -
?
1-phosphatidyl-1D-myo-inositol + 6-((N-(7-nitrobenz-2-oxa-1,3-diazol-4-yl)amino)-hexanoyl)-sphingosine
?
Substrates: -
Products: -
Products: -
?
1-phosphatidyl-1D-myo-inositol + N-[6-[(7-nitro-2-1,3-benzoxadiazol-4-yl)amino]hexanoyl]-D-erythro-sphingosine
?
-
Substrates: -
Products: -
Products: -
?
1-phosphatidyl-1D-myo-inositol + N-[6-[(7-nitro-2-1,3-benzoxadiazol-4-yl)amino]hexanoyl]-D-erythro-sphingosine
?
Aspergillus flavus ATCC 9643
-
Substrates: -
Products: -
Products: -
?
1-phosphatidyl-1D-myo-inositol + N-[6-[(7-nitro-2-1,3-benzoxadiazol-4-yl)amino]hexanoyl]-D-erythro-sphingosine
?
-
Substrates: -
Products: -
Products: -
?
1-phosphatidyl-1D-myo-inositol + N-[6-[(7-nitro-2-1,3-benzoxadiazol-4-yl)amino]hexanoyl]-D-erythro-sphingosine
?
-
Substrates: -
Products: -
Products: -
?
1-phosphatidyl-1D-myo-inositol + N-[6-[(7-nitro-2-1,3-benzoxadiazol-4-yl)amino]hexanoyl]-D-erythro-sphingosine
?
-
Substrates: -
Products: -
Products: -
?
1-phosphatidyl-1D-myo-inositol + N-[6-[(7-nitro-2-1,3-benzoxadiazol-4-yl)amino]hexanoyl]-D-erythro-sphingosine
?
-
Substrates: -
Products: -
Products: -
?
1-phosphatidyl-1D-myo-inositol + N-[6-[(7-nitro-2-1,3-benzoxadiazol-4-yl)amino]hexanoyl]-D-erythro-sphingosine
?
-
Substrates: -
Products: -
Products: -
?
1-phosphatidyl-1D-myo-inositol + N-[6-[(7-nitro-2-1,3-benzoxadiazol-4-yl)amino]hexanoyl]-D-erythro-sphingosine
?
[Candida] glabrata ATCC 90030
-
Substrates: -
Products: -
Products: -
?
additional information
?
-
Substrates: 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
Products: -
Products: -
?
additional information
?
-
-
Substrates: 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
Products: -
Products: -
?
additional information
?
-
-
Substrates: maximum product formation is observed at 1-phosphatidyl-1D-myo-inositol concentrations in excess of 600 microM
Products: -
Products: -
?
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
(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
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
N-dodecyl-N,N-(dimethylammonio)butanoate
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
-
IC50 value 3.4 ng/ml. All Candida species tested are well susceptible to aureobasidin A with MICs below 2 microg/ml
aureobasidin A
-
inhibits Aur1, activates vacuolar acidification and strongly induces the cell wall integrity pathway
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
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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DISEASE
TITLE OF PUBLICATION
LINK TO PUBMED
Chagas Disease
The Sphingolipid Biosynthetic Pathway Is a Potential Target for Chemotherapy against Chagas Disease.
Hypersensitivity
Crosstalk between protein kinase A and the HOG pathway under impaired biosynthesis of complex sphingolipids in budding yeast.
Leishmaniasis
Molecular docking and molecular dynamics simulation study of inositol phosphorylceramide synthase - inhibitor complex in leishmaniasis: Insight into the structure based drug design.
Mycoses
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.
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.138
1-phosphatidyl-1D-myo-inositol
CHAPS-washed membranes, pH 7.5, 23Ā°C
0.003
6-((N-(7-nitrobenz-2-oxa-1,3-diazol-4-yl)amino)-hexanoyl)-sphingosine
pH 7.0, 23Ā°C
0.0033
6-((N-(7-nitrobenz-2-oxa-1,3-diazol-4-yl)amino)-hexanoyl)-sphingosine
pH 7.0, 23Ā°C
0.0033
6-((N-(7-nitrobenz-2-oxa-1,3-diazol-4-yl)amino)-hexanoyl)-sphingosine
CHAPS-washed membranes, pH 7.5, 23Ā°C
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Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.008
(1R)-1-cyclohexyl-5-(3,4-dimethoxyphenyl)-3-methyl-2-oxopentyl 3-hydroxy-N-methyl-N-(2-propylpentanoyl)valinate
pH 7.0, 23Ā°C
0.011
(1R)-1-cyclohexyl-5-(3,4-dimethoxyphenyl)-3-methyl-2-oxopentyl 3-hydroxy-N-methyl-N-(6-phenylhexanoyl)valinate
pH 7.0, 23Ā°C
0.012
(1R)-1-cyclohexyl-5-(3,4-dimethoxyphenyl)-3-methyl-2-oxopentyl 3-hydroxy-N-methyl-N-nonanoylvalinate
pH 7.0, 23Ā°C
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IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0147
(2R,4E)-2-aminooctadec-4-en-1-ol
Leishmania major
pH not specified in the publication, temperature not specified in the publication
0.588
1-phosphatidyl-1D-myo-inositol
Candida albicans
CHAPS-washed membranes, pH 7.5, 23Ā°C
0.004
4-(2,5-dimethyl-4-[(E)-[(piperidin-1-yl)methylidene]amino]phenoxy)-2-(2,2-dimethylpropyl)benzonitrile
Arabidopsis thaliana
pH 7.4, 30Ā°C
0.0132
N-[(2R,4E)-1-hydroxyoctadec-4-en-2-yl]-2-phenylacetamide
Leishmania major
pH not specified in the publication, temperature not specified in the publication
0.0048
N-[(2S,4E)-3-hydroxyoctadec-4-en-2-yl]octanamide
Leishmania major
pH not specified in the publication, temperature not specified in the publication
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
134
-
pH not specified in the publication, temperature not specified in the publication
211
-
pH not specified in the publication, temperature not specified in the publication
333
-
pH not specified in the publication, temperature not specified in the publication
6.1
-
pH not specified in the publication, temperature not specified in the publication
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pI VALUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
Q06346 i.e. regulatory subunit Kei1, P36107 i.e. catalytic subunit Aur1
Q06346; P36107
UniProt
brenda
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
additional information
additional information
transcripts are expressed at low levels in all tissues
brenda
additional information
transcripts are expressed at low levels in all tissues
brenda
additional information
transcripts are expressed at low levels in all tissues
brenda
additional information
transcripts are expressed at low levels in cauline leaves, rosette leaves, roots and stems
brenda
additional information
transcripts are expressed at low levels in cauline leaves, rosette leaves, roots and stems
brenda
additional information
transcripts are expressed at low levels in cauline leaves, rosette leaves, roots and stems
brenda
additional information
transcripts are expressed in cauline leaves, rosette leaves, roots, flowers, siliques and stems
brenda
additional information
transcripts are expressed in cauline leaves, rosette leaves, roots, flowers, siliques and stems
brenda
additional information
transcripts are expressed in cauline leaves, rosette leaves, roots, flowers, siliques and stems
brenda
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
the enzyme's active site is in the lumen
brenda
Highest Expressing Human Cell Lines
Cell Line LinksPlease wait a moment until the data is sorted. This message will disappear when the data is sorted.
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
physiological function
physiological function
a strain lacking Aur1 activity fails to incorporate inositol or N-acetylsphinganine into sphingolipids and lacks enzyme activity
physiological function
expression in HEK 293 cells leads to the synthesis of an inositol phosphorylceramide-like species
physiological function
isoforms IPCS1-3 complement an Aur11 auxotrophic mutant yeast strain and confer aureobasidin A resistance
physiological function
overexpression of inositol phosphorylceramide synthase isoforms IPCS1, 2 or 3 in Arabidopsis thaliana results in the downregulation of genes involved in plant response to pathogens. In addition, genes associated with the abiotic stress response to salinity, cold and drought are similarly downregulated. The degree of downregulation is specifically correlated with the level of IPCS expression
physiological function
Saccharomyces cerevisiae transformants harboring AUR1 mutantY166F/G249C are resistant to aureobasidin A
physiological function
Q06346; P36107
the growth defect of a temperature-sensitive mutant is effectively suppressed by the overexpression of Aur1, and Aur1 and Kei1 proteins form a complex in vivo. The temperature-sensitive mutant is hypersensitive to aureobasidin A, a specific inhibitor of IPC synthesis, and the IPC synthase activity in the mutant membranes is thermolabile. A part of Aur1 is missorted to the vacuole in Kei1 mutant cells. Aur1 without Kei1 has hardly detectable IPC synthase activity
physiological function
-
upon downregulation of Aur1 expression, the accumulation of ceramides can lead to cell death. Vesicle-mediated transport between Golgi apparatus, endosomes, and vacuole becomes crucial for survival when Aur1 is repressed, irrespective of the mode of repression. Vacuolar acidification becomes essential when cells are acutely stressed by aureobasidin A. Aureobasidin A activates vacuolar acidification and strongly induces the cell wall integrity pathway
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UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). IPCS2_ARATH
305
3
34996
Swiss-Prot
Mitochondrion (Reliability: 5)
AUR1_YEAST
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
401
6
45193
Swiss-Prot
other Location (Reliability: 5)
GINT1_ARATH
765
3
86431
Swiss-Prot
other Location (Reliability: 1)
AUR1_CANAL
Candida albicans (strain SC5314 / ATCC MYA-2876)
471
0
53458
Swiss-Prot
-
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Y166F/G249C
mutant protein confers resistance to aureobasidin when expressed in Saccharomyces cerevisiae
additional information
-
a mutant strain with loss of an intron displays resistance to aureobasidin A
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
detergents Triton X-100, Nonidet P-40, Brij, Tween20, Tween 80 and octylglucoside all inactivate the enzyme. At moderate concentrations, the activity of the Triton X-100- and octylglucoside-solubilized material can be partially restored by inclusion of 5 mM phosphatidylinositol in the solubilization buffer. Detergents Empigen BB, N-dodecyl-N,N-(dimethylammonio)butanoate, Zwittergent 3-10, and amidosulfobetaine-16 all inactivate the enzyme essentially irreversibly. IPC synthase activity in membranes remaines largely intact and sedimentable at CHAPS concentrations of 4% where more than 90% of the phospholipids and 60% of the total proteins are extracted from the membranes
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
isoforms IPCS1 and IPCS3 display low expression compared to isoform IPCS2
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APPLICATION