Information on EC 3.5.1.23 - ceramidase

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The expected taxonomic range for this enzyme is: Eukaryota, Bacteria

EC NUMBER
COMMENTARY hide
3.5.1.23
-
RECOMMENDED NAME
GeneOntology No.
ceramidase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
a ceramide + H2O = a carboxylate + sphingosine
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
deacylation
hydrolysis
hydrolysis of peptide bond
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-
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
ceramide degradation
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fatty acid alpha-oxidation III
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Metabolic pathways
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Sphingolipid metabolism
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sphingolipid recycling and degradation (yeast)
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sphingosine and sphingosine-1-phosphate metabolism
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sphingosine metabolism
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SYSTEMATIC NAME
IUBMB Comments
N-acylsphingosine amidohydrolase
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CAS REGISTRY NUMBER
COMMENTARY hide
37289-06-8
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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UniProt
Manually annotated by BRENDA team
gene asahA
UniProt
Manually annotated by BRENDA team
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-
Manually annotated by BRENDA team
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-
Manually annotated by BRENDA team
gene CG13969
UniProt
Manually annotated by BRENDA team
no activity in Saccharomyces cerevisiae
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
strain AN17, gene cdase or PA0845
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Manually annotated by BRENDA team
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UniProt
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
evolution
malfunction
metabolism
physiological function
additional information
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(2R,3Z)-2-([(2E)-1-hydroxy-12-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]dodec-2-en-1-yl]amino)heptadec-3-ene-1,3-diol + H2O
?
show the reaction diagram
-
9.9% hydrolysis
-
-
ir
(4E,2S,3R)-2-N-(10-pyrenedecanoyl)-1,3,17-trihydroxy-17-(3,5-dinitrobenzoyl)-4-heptadecene + H2O
?
show the reaction diagram
11-eicosenoyl-ceramide + H2O
sphingosine + 11-eicosenoic acid
show the reaction diagram
-
-
-
-
?
11-eicosenoyl-dihydroceramide + H2O
dihydrosphingosine + 11-eicosenoic acid
show the reaction diagram
-
-
-
-
?
11-eicosenoyl-phytoceramide + H2O
phytosphingosine + 11-eicosenoic acid
show the reaction diagram
-
-
-
-
?
11-[[9-(diethylamino)-5-oxo-5H-benzo[a]phenoxazin-2-yl]oxy]-N-[(2S,3R,4E)-1,3-dihydroxy-7-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]hept-4-en-2-yl]undecanamide + H2O
?
show the reaction diagram
4-nitrobenzo-2-oxa-1,3-diazole-C12-ceramide + H2O
4-nitrobenzo-2-oxa-1,3-diazole-dodecanoic acid + ceramide
show the reaction diagram
4-nitrobenzo-2-oxa-1,3-diazole-ceramide + H2O
?
show the reaction diagram
4-nitrobenzo-2-oxa-1,3-diazole-N-dodecanoylsphingosine + H2O
?
show the reaction diagram
-
-
-
-
?
4-nitrobenzo-2-oxa-1,3-diazole-N-hexanoylsphingosine + H2O
?
show the reaction diagram
-
-
-
-
?
4-nitrobenzo-2-oxa-1,3-diazoyl-N-dodecanoylsphingosine + H2O
4-nitrobenzo-2-oxa-1,3-diazoyl-dodecanoic acid + sphingosine
show the reaction diagram
7-nitrobenz-2-oxa-1,3-diazole-N-lauroylsphingosine + H2O
?
show the reaction diagram
-
-
-
-
r
C12-4-nitrobenzo-2-oxa-1,3-diazole-ceramide + H2O
?
show the reaction diagram
C12-NBD-Cer + H2O
NBD-dodecanoic acid + D-erythro-sphingosine
show the reaction diagram
-
the enzyme catalyzes also the reverse reaction of ceramide synthesis
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-
r
C12-NBD-Cer + H2O
NBD-dodecanoic acid + sphingosine
show the reaction diagram
C12:0-ceramide + H2O
laurate + sphingosine
show the reaction diagram
-
-
-
-
?
C14:0-ceramide + H2O
myristate + sphingosine
show the reaction diagram
-
-
-
-
?
C16:0-ceramide + H2O
palmitate + sphingosine
show the reaction diagram
-
-
-
-
?
C18:0-ceramide + H2O
stearate + sphingosine
show the reaction diagram
-
-
-
-
?
C18:1-ceramide + H2O
oleate + sphingosine
show the reaction diagram
-
-
-
-
?
C20:0-ceramide + H2O
eicosanoic acid + sphingosine
show the reaction diagram
-
-
-
-
?
C20:1-ceramide + H2O
C20:1 fatty acid + sphingosine
show the reaction diagram
-
-
-
-
?
C24-ceramide + H2O
C24 fatty acid + sphingosine
show the reaction diagram
-
-
-
r
C24:0-ceramide + H2O
C24:0 fatty acid + sphingosine
show the reaction diagram
-
-
-
-
?
C24:1-ceramide + H2O
C24:1 fatty acid + sphingosine
show the reaction diagram
-
-
-
-
?
C6:0-ceramide + H2O
hexanoate + sphingosine
show the reaction diagram
-
-
-
-
?
ceramide + H2O
?
show the reaction diagram
-
substrate with about 30% activity of GM2
-
-
?
ceramide + H2O
carboxylate + sphingosine
show the reaction diagram
-
-
-
?
ceramide + H2O
sphingosine + a fatty acid
show the reaction diagram
-
-
sphongosine is an apoptosis mediator
-
?
ceramide + H2O
sphingosine + fatty acid
show the reaction diagram
D-erythro-4-nitrobenzo-2-oxa-1,3-diazole-C12-ceramide + H2O
D-erythro-4-nitrobenzo-2-oxa-1,3-diazole-dodecanoic acid + ceramide
show the reaction diagram
D-erythro-C12-4-nitrobenzo-2-oxa-1,3-diazole-ceramide + H2O
D-erythro-sphingosine + ?
show the reaction diagram
-
substrate activity assay
-
-
?
D-erythro-C12-4-nitrobenzo-2-oxa-1,3-diazole-phytoceramide + H2O
D-erythro-sphingosine + ?
show the reaction diagram
-
substrate activity assay
-
-
?
D-erythro-C12-NBD-ceramide + H2O
D-erythro-sphingosine + 4-nitrobenzo-2-oxa-1,3-diazoyl-dodecanoic acid
show the reaction diagram
D-erythro-C24:1-ceramide + H2O
C24:1 fatty acid + D-erythro-sphingosine
show the reaction diagram
-
-
-
-
?
D-erythro-dihydrosphingosine + fatty acid
?
show the reaction diagram
-
very low ceramide synthesis activity
-
-
?
D-erythro-dodecanoyl-7-nitrobenz-2-oxa-1,3-diazol-4-yl-ceramide + H2O
12-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]dodecanoic acid + sphingosine
show the reaction diagram
D-erythro-myristoyl-sphingosine + H2O
myristate + sphingosine
show the reaction diagram
-
-
-
?
D-erythro-octadecanoyl-ceramide + H2O
D-erythro-sphingosine + palmitic acid
show the reaction diagram
-
mtCDase specifically hydrolyzes the D-erythro-isomer of ceramide, requirements for ceramide-enzyme interaction, ligand interaction with the enzyme occurs in a high affinity low specificity manner, in contrast to catalysis which is highly specific for D-erythro-ceramide but occurs with a lower affinity
-
-
?
D-erythro-oleoyl-sphingosine + H2O
oleate + sphingosine
show the reaction diagram
-
-
-
?
D-erythro-palmitoyl-sphingosine + H2O
palmitate + sphingosine
show the reaction diagram
-
-
-
?
D-erythro-sphingosine + (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexa-4,7,10,13,16,19-enoic acid
N-((4Z,7Z,10Z,13Z,16Z,19Z)-docosahexa-4,7,10,13,16,19-enoyl)-D-erythro-sphingosine + H2O
show the reaction diagram
-
50% of activity
-
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r
D-erythro-sphingosine + arachidonic acid
N-arachidonyl-D-erythro-sphingosine + H2O
show the reaction diagram
-
61% of activity
-
-
r
D-erythro-sphingosine + behenic acid
N-behenoyl-D-erythro-sphingosine + H2O
show the reaction diagram
-
24% of activity
-
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r
D-erythro-sphingosine + cerotic acid
N-cerotoyl-D-erythro-sphingosine + H2O
show the reaction diagram
-
4% of activity
-
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r
D-erythro-sphingosine + eicosapentaenoic acid
N-eicosapentaenyl-D-erythro-sphingosine + H2O
show the reaction diagram
-
52% of activity
-
-
r
D-erythro-sphingosine + fatty acid
?
show the reaction diagram
-
highest ceramide synthesis activity with D-erythro-sphingosine
-
-
?
D-erythro-sphingosine + fatty acid
N-acyl-D-erythro-sphingosine + H2O
show the reaction diagram
-
-
-
-
r
D-erythro-sphingosine + lauric acid
N-lauroyl-D-erythro-sphingosine + H2O
show the reaction diagram
-
72% of activity
-
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r
D-erythro-sphingosine + lignoceric acid
N-lignoceroyl-D-erythro-sphingosine + H2O
show the reaction diagram
-
6% of activity
-
-
r
D-erythro-sphingosine + linoleic acid
N-linoleoyl-D-erythro-sphingosine + H2O
show the reaction diagram
-
66% of activity
-
-
r
D-erythro-sphingosine + myristic acid
N-myristoyl-D-erythro-sphingosine + H2O
show the reaction diagram
-
best substrate
-
-
r
D-erythro-sphingosine + oleic acid
N-oleoyl-D-erythro-sphingosine + H2O
show the reaction diagram
-
39% of activity
-
-
r
D-erythro-sphingosine + palmitic acid
N-palmitoyl-D-erythro-sphingosine + H2O
show the reaction diagram
-
70% of activity, palmitic acid can not be replaced with palmityl-CoA
-
-
r
D-erythro-sphingosine + stearic acid
N-stearoyl-D-erythro-sphingosine + H2O
show the reaction diagram
-
49% of activity
-
-
r
D-erythro-tetracosanoyl-sphingosine + H2O
tetracosanoate + sphingosine
show the reaction diagram
i.e. D-e-C24:0-ceramide
-
-
?
D-threo-sphingosine + fatty acid
?
show the reaction diagram
-
low ceramide synthesis activity
-
-
?
dihydro-C16-ceramide + H2O
?
show the reaction diagram
-
-
-
-
?
dihydro-N-myristoyl-D-erythro-sphingosine + H2O
dihydro-D-erythro-sphingosine + myristate
show the reaction diagram
-
55.9% hydrolysis compared to N-palmitoyl-D-erythro-sphingosine
-
-
?
dihydro-N-palmitoyl-D-erythro-sphingosine + H2O
dihydro-D-erythro-sphingosine + palmitate
show the reaction diagram
-
4.5% hydrolysis compared to N-palmitoyl-D-erythro-sphingosine
-
-
?
dihydroceramide + H2O
dihydrosphingosine + fatty acid
show the reaction diagram
-
-
-
-
?
ganglioside + H2O
lyso-ganglioside + fatty acid
show the reaction diagram
-
GM1, GM2, GM3
corresponding to ganglioside type
?
ganglioside GM2 + H2O
?
show the reaction diagram
-
sphingolipid, best substrate
-
-
?
hexadecanoyl-ceramide + H2O
hexadecanoate + sphingosine
show the reaction diagram
i.e. C16-ceramide
-
-
r
L-erythro-sphingosine + fatty acid
?
show the reaction diagram
-
low ceramide synthesis activity
-
-
?
L-threo-sphingosine + fatty acid
?
show the reaction diagram
-
low ceramide synthesis activity
-
-
?
linoleoylsphingosine + H2O
linoleic acid + sphingosine
show the reaction diagram
-
-
-
-
?
myristic acid + sphingosine
N-myristoylsphingosine + H2O
show the reaction diagram
-
highest ceramide synthesis activity with myristic acid
-
-
?
N-((2S,3R)-1,3-dihydroxy-5-((2-oxo-2H-chromen-7-yl)oxy)pentan-2-yl)palmitamide + H2O
palmitate + 2-amino-2,4-dideoxy-5-O-(2-oxo-2H-chromen-7-yl)-D-erythro-pentitol
show the reaction diagram
-
-
-
-
?
N-acetylsphingosine + H2O
acetic acid + sphingosine
show the reaction diagram
-
-
-
-
?
N-acyl-sphingosine + H2O
a carboxylate + sphingosine
show the reaction diagram
N-acylsphingosine + H2O
a carboxylate + sphingosine
show the reaction diagram
N-acylsphingosine + H2O
carboxylate + sphingosine
show the reaction diagram
N-arachidonoyl-ceramide + H2O
sphingosine + arachidonate
show the reaction diagram
-
-
-
-
?
N-arachidonoyl-dihydroceramide + H2O
dihydrosphingosine + arachidonate
show the reaction diagram
-
-
-
-
?
N-arachidonoyl-phytoceramide + H2O
phytosphingosine + arachidonate
show the reaction diagram
-
-
-
-
?
N-arachidoyl-D-erythro-sphingosine + H2O
arachidonate + D-erythro-sphingosine
show the reaction diagram
-
low activity
-
-
?
N-caproylsphingosine + H2O
caproate + sphingosine
show the reaction diagram
-
about 25% activity compared to N-oleoylsphingosine
-
-
?
N-dodecanoyl-7-nitrobenz-2-oxa-1,3,4-diazole-D-erythro-dihydrosphingosine + H2O
12-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]dodecanoate + D-erythro-dihydrosphingosine
show the reaction diagram
-
-
-
-
r
N-dodecanoyl-7-nitrobenz-2-oxa-1,3,4-diazole-D-erythro-phytosphingosine + H2O
12-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]dodecanate + D-erythro-phytosphingosine
show the reaction diagram
-
-
-
-
r
N-dodecanoyl-7-nitrobenz-2-oxa-1,3,4-diazole-D-erythro-sphingosine + H2O
12-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]dodecanate + D-erythro-sphingosine
show the reaction diagram
-
i.e. C12-NBD-Cer
-
-
r
N-hexanoyl-D-erythro-sphingosine + H2O
hexanoate + D-erythro-sphingosine
show the reaction diagram
N-hexanoyl-D-erythro-sphingosine + H2O
sphingosine + hexanoate
show the reaction diagram
-
100.3% hydrolysis compared to N-palmitoyl-D-erythro-sphingosine
-
-
?
N-hexanoyl-sphingosine + H2O
hexanoate + sphingosine
show the reaction diagram
-
-
-
-
?
N-hexanoylsphingosine + H2O
hexanoic acid + sphingosine
show the reaction diagram
-
-
-
-
?
N-lauroyl-D-erythro-sphingosine + H2O
laurate + D-erythro-sphingosine
show the reaction diagram
N-lauroyl-D-erythro-sphingosine + H2O
sphingosine + dodecanoate
show the reaction diagram
-
most efficient substrate, 293.2% hydrolysis compared to N-palmitoyl-D-erythro-sphingosine
-
-
r
N-lauroylceramide + H2O
laureate + sphingosine
show the reaction diagram
-
-
-
?
N-lauroylsphingosine + H2O
laurate + sphingosine
show the reaction diagram
N-lauroylsphingosine + H2O
lauric acid + sphingosine
show the reaction diagram
N-laurylsphingosine + H2O
laureate + sphingosine
show the reaction diagram
-
-
-
-
?
N-lignoceroyl-D-erythro-sphingosine + H2O
lignocerate + D-erythro-sphingosine
show the reaction diagram
N-lignoceroyl-D-erythro-sphingosine + H2O
sphingosine + tetracosanoate
show the reaction diagram
-
25.1% hydrolysis compared to N-palmitoyl-D-erythro-sphingosine
-
-
?
N-myristoyl-D-erythro-sphingosine + H2O
myristate + D-erythro-sphingosine
show the reaction diagram
-
best substrate
-
-
?
N-myristoyl-D-erythro-sphingosine + H2O
sphingosine + myristate
show the reaction diagram
-
212.2% hydrolysis compared to N-palmitoyl-D-erythro-sphingosine
-
-
?
N-myristoyl-D-sphingosine + H2O
?
show the reaction diagram
-
-
-
-
?
N-nervonoyl-D-erythro-sphingosine + H2O
nervonoate + D-erythro-sphingosine
show the reaction diagram
-
-
-
-
?
N-nervonoylsphingosine + H2O
nervonate + sphingosine
show the reaction diagram
-
about 80% activity compared to N-oleoylsphingosine
-
-
?
N-octanoylsphinganine + H2O
octanoic acid + sphingosine
show the reaction diagram
-
-
-
-
?
N-octanoylsphingosine + H2O
octanoic acid + sphingosine
show the reaction diagram
N-oleoyl-ceramide + H2O
sphingosine + oleate
show the reaction diagram
-
-
-
-
?
N-oleoyl-D-erythro-ceramide + H2O
oleate + D-erythro-sphingosine
show the reaction diagram
N-oleoyl-D-erythro-sphingosine + H2O
oleate + D-erythro-sphingosine
show the reaction diagram
-
-
-
-
?
N-oleoyl-dihydroceramide + H2O
dihydrosphingosine + oleate
show the reaction diagram
-
-
-
-
?
N-oleoyl-phytoceramide + H2O
phytosphingosine + oleate
show the reaction diagram
-
-
-
-
?
N-oleoylsphingosine + H2O
oleate + sphingosine
show the reaction diagram
-
100% activity
-
-
?
N-oleoylsphingosine + H2O
oleic acid + sphingosine
show the reaction diagram
N-oleyldihydro-sphingosine + H2O
?
show the reaction diagram
-
-
-
-
r
N-palmitoyl sphingosine + H2O
palmitic acid + sphingosine
show the reaction diagram
N-palmitoyl-D-erythro-sphingosine + H2O
D-erythro-sphingosine + palmitic acid
show the reaction diagram
-
-
-
-
?
N-palmitoyl-D-erythro-sphingosine + H2O
palmitate + D-erythro-sphingosine
show the reaction diagram
N-palmitoyl-D-erythro-sphingosine + H2O
sphingosine + palmitate
show the reaction diagram
-
100% hydrolysis
-
-
r
N-palmitoyldihydrosphingosine + H2O
?
show the reaction diagram
-
-
-
-
r
N-palmitoylphytosphingosine + H2O
?
show the reaction diagram
N-palmitoylsphinganine + H2O
palmitate + sphinganine
show the reaction diagram
low hydrolysis rate
-
-
?
N-palmitoylsphinganine + H2O
palmitoic acid + sphinganine
show the reaction diagram
N-palmitoylsphingosine + H2O
palmitate + sphingosine
show the reaction diagram
N-palmitoylsphingosine + H2O
palmitic acid + sphingosine
show the reaction diagram
N-stearoyl-D-erythro-sphingosine + H2O
sphingosine + stearate
show the reaction diagram
-
98.5% hydrolysis compared to N-palmitoyl-D-erythro-sphingosine
-
-
?
N-stearoyl-D-erythro-sphingosine + H2O
stearate + D-erythro-sphingosine
show the reaction diagram
N-stearoylphytosphingosine + H2O
?
show the reaction diagram
N-stearoylsphinganine + H2O
stearate + sphinganine
show the reaction diagram
low hydrolysis rate
-
-
?
N-stearoylsphinganine + H2O
stearic acid + sphinganine
show the reaction diagram
N-stearoylsphingosine + H2O
stearate + sphingosine
show the reaction diagram
less efficient hydrolysis than of N-lauroylsphingosine and N-palmitoylsphingosine
-
-
?
N-stearoylsphingosine + H2O
stearic acid + sphingosine
show the reaction diagram
N-[(2S,3R,4E)-1,3-dihydroxy-14-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]tetradec-4-en-2-yl]hexadecanamide + H2O
?
show the reaction diagram
N-[(2S,3R,4E)-1,3-dihydroxynonadec-4-en-2-yl]-12-[[9-(ethylamino)-5-oxo-5H-benzo[a]phenoxazin-2-yl]oxy]dodecanamide + H2O
?
show the reaction diagram
N-[(2S,3R,4E)-13-[[9-(ethylamino)-5-oxo-5H-benzo[a]phenoxazin-2-yl]oxy]-1,3-dihydroxytridec-4-en-2-yl]hexadecanamide + H2O
?
show the reaction diagram
N-[(2S,3R,4E)-7-[[9-(diethylamino)-5-oxo-5H-benzo[a]phenoxazin-3-yl]oxy]-1,3-dihydroxyhept-4-en-2-yl]-11-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]undecanamide + H2O
?
show the reaction diagram
N-[12-[(7-nitro-2-1,3-benzoxadiazol-4-yl)amino]lauroyl]-phytosphingosine + H2O
N-12-[(7-nitro-2-1,3-benzoxadiazol-4-yl)amino]laurate + phytosphingosine
show the reaction diagram
-
i.e. D-ribo-C12-NBD-phytoceramide
-
-
?
N-[12-[(7-nitro-2-1,3-benzoxadiazol-4-yl)amino]lauroyl]-sphingosine + H2O
N-12-[(7-nitro-2-1,3-benzoxadiazol-4-yl)amino]laurate + sphingosine
show the reaction diagram
i.e. C12-NBD-ceramide
-
-
r
octadecanoyl-ceramide + H2O
octadecanoate + sphingosine
show the reaction diagram
i.e. C18-ceramide
-
-
r
octanoyl-D-erythro-sphingosine + H2O
?
show the reaction diagram
-
substrate activity assay
-
-
?
octanoyl-sphingosine + H2O
octanoate + sphingosine
show the reaction diagram
-
-
-
-
?
palmitoyl sphingosine + H2O
palmitate + sphingosine
show the reaction diagram
palmitoyl-D-[erythro-9,10]sphingosine + H2O
palmitate + D-erythro-sphingosine
show the reaction diagram
-
-
-
-
?
palmitoyl-sphingosine + H2O
palmitate + sphingosine
show the reaction diagram
phytoceramide + H2O
phytosphingosine + fatty acid
show the reaction diagram
-
-
-
-
?
sphingosine + fatty acid
ceramide
show the reaction diagram
-
-
-
r
sphingosine + myristic acid + H2O
C14-ceramide
show the reaction diagram
-
at pH 8.0
-
-
?
additional information
?
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
C12:0-ceramide + H2O
laurate + sphingosine
show the reaction diagram
-
-
-
-
?
C14:0-ceramide + H2O
myristate + sphingosine
show the reaction diagram
-
-
-
-
?
C16:0-ceramide + H2O
palmitate + sphingosine
show the reaction diagram
-
-
-
-
?
C18:0-ceramide + H2O
stearate + sphingosine
show the reaction diagram
-
-
-
-
?
C18:1-ceramide + H2O
oleate + sphingosine
show the reaction diagram
-
-
-
-
?
C20:0-ceramide + H2O
eicosanoic acid + sphingosine
show the reaction diagram
-
-
-
-
?
C20:1-ceramide + H2O
C20:1 fatty acid + sphingosine
show the reaction diagram
-
-
-
-
?
C24:0-ceramide + H2O
C24:0 fatty acid + sphingosine
show the reaction diagram
-
-
-
-
?
C6:0-ceramide + H2O
hexanoate + sphingosine
show the reaction diagram
-
-
-
-
?
ceramide + H2O
carboxylate + sphingosine
show the reaction diagram
Q13510
-
-
-
?
ceramide + H2O
sphingosine + a fatty acid
show the reaction diagram
-
-
sphongosine is an apoptosis mediator
-
?
ceramide + H2O
sphingosine + fatty acid
show the reaction diagram
D-erythro-C24:1-ceramide + H2O
C24:1 fatty acid + D-erythro-sphingosine
show the reaction diagram
-
-
-
-
?
D-erythro-myristoyl-sphingosine + H2O
myristate + sphingosine
show the reaction diagram
Q5QJU3
-
-
-
?
D-erythro-oleoyl-sphingosine + H2O
oleate + sphingosine
show the reaction diagram
Q5QJU3
-
-
-
?
D-erythro-palmitoyl-sphingosine + H2O
palmitate + sphingosine
show the reaction diagram
Q5QJU3
-
-
-
?
D-erythro-tetracosanoyl-sphingosine + H2O
tetracosanoate + sphingosine
show the reaction diagram
Q5QJU3
i.e. D-e-C24:0-ceramide
-
-
?
dihydroceramide + H2O
dihydrosphingosine + fatty acid
show the reaction diagram
-
-
-
-
?
N-acyl-sphingosine + H2O
a carboxylate + sphingosine
show the reaction diagram
-
the Asah2-encoded neutral ceramidase is a key enzyme for the catabolism of dietary sphingolipids and regulates the cellular levels of bioactive sphingolipid metabolites, ceramide, sphingosine, and sphingosine 1-phosphate, in the intestinal tract
-
-
?
N-acylsphingosine + H2O
a carboxylate + sphingosine
show the reaction diagram
N-acylsphingosine + H2O
carboxylate + sphingosine
show the reaction diagram
N-lauroylsphingosine + H2O
laurate + sphingosine
show the reaction diagram
-
-
-
-
?
N-oleoyl-D-erythro-ceramide + H2O
oleate + D-erythro-sphingosine
show the reaction diagram
phytoceramide + H2O
phytosphingosine + fatty acid
show the reaction diagram
-
-
-
-
?
additional information
?
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
additional information
-
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Ba2+
better activator than Mg2+
Cu2+
activate about 18% at 5 mM
NaCl
at 150 mM NaCl, acer-1 seedlings dramatically loose vitality compared with the wild-type, the amiR-ACER-1 seedlings are the most sensitive to salt, showing obvious differences from the other genotypes after 100 mM NaCl treatment for 12 days
additional information
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(1R, 2R)-2-(N-tetradecanoylamino)-1-(4-nitrophenyl)-1,3-propanediol
-
inhibits in vitro
(1R,2R)-2-(N-tetradecanoylamino)-1-(4-nitrophenyl)-1,3-propanediol
(1R,2R)-2-N-myristoylamino-1-(4-nitrophenyl)-1,3-propandiol
(1S, 2R)-D-erythro-2-(N-myristoylamino)-1-phenyl-1-propanol
inhibitor of alkaline ceramidase; inhibitor of alkaline ceramidase; inhibitor of neutral ceramidase
(1S,2R)-2-N-myristoylamino-1-phenyl-1-propanol
(1S,2R)-D-erythro-2-(N-myristoylamino)-1-phenyl-1-propanol
(2E,4E)-N-[(2S,3R)-1,3-dihydroxyoctadecan-2-yl]hexa-2,4-dienamide
-
-
(2S)-3-keto-dehydrosphingosine
-
mtCDase, weak inhibition
-
(2S)-3-keto-hexadecanoyl-ceramide
-
mtCDase, IC50: 0.6 mol%
-
(2S)-3-keto-sphinganine
-
mtCDase, IC50: 0.34 mol%
-
(2S)-3-keto-sphingosine
-
mtCDase, weak inhibition
-
(E)-4-[(2S,3R)-N-1,3-dihydroxyoctadecan-2-ylamino]4-oxo-2-butenoic acid
-
-
(E)-N-[(2S,3R)-1,3-dihydroxyoctadecan-2-yl]but-2-enamide
-
-
1-ethyl-3-(3-dimethylaminopropyl)carbodiimide
-
modification of carboxyl groups completely inhibits forward and reverse reaction
1-O-methyl-D-erythro-sphingosine
-
mtCDase, weak inhibition
12-amino-N-[(1R,2R)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]dodecanamide
-
-
1R,2R-(2-N-myristoylamino-1-(4-nitrophenyl)-1,3-dihydroxypropane)
1S,2S-(2-N-myristoylamino-1-(4-nitrophenyl)-1,3-dihydroxypropane)
2,3-Butanedione
-
modification of Arg causes about 50% inhibition of forward and reverse reaction
2-mercaptoethanol
2-oxo-N-(4-phenylbutyl)-1,3-benzoxazole-3(2H)-carboxamide
3-(cyclopropylmethyl)-5-fluoro-N-hexyl-2,4-dioxopyrimidine-1-carboxamide
-
-
3-benzoyl-5-fluoro-N-hexyl-2,4-dioxopyrimidine-1-carboxamide
-
-
3-ethyl-5-fluoro-N-hexyl-2,4-dioxopyrimidine-1-carboxamide
-
-
5-(benzyl(methyl)amino)-N-hexyl-2,4-dioxopyrimidine-1-carboxamide
-
-
5-chloro-N-hexyl-2,4-dioxo-3,4-dihydropyrimidine-1(2H)-carboxamide
-
-
5-chloro-N-hexyl-2,4-dioxo-pyrimidine-1-carboxamide
5-cyano-N-hexyl-2,4-dioxo-3,4-dihydropyrimidine-1(2H)-carboxamide
-
-
5-ethyl-N-hexyl-2,4-dioxopyrimidine-1-carboxamide
-
-
5-fluoro-N-hexyl-2,4-dioxo-3,4-dihydropyrimidine-1(2H)-carboxamide
-
-
5-fluoro-N-hexyl-3-(2-methylpropanoyl)-2,4-dioxopyrimidine-1-carboxamide
-
-
5-fluoro-N-hexyl-3-methyl-2,4-dioxopyrimidine-1-carboxamide
-
-
5-fluoro-N-octyl-2,4-dioxopyrimidine-1-carboxamide
-
-
5-trifluoromethyl-N-hexyl-2,4-dioxo-pyrimidine-1-carboxamide
6-(4-fluorophenyl)-2-oxo-N-(4-phenylbutyl)-1,3-benzoxazole-3(2H)-carboxamide
-
-
6-(4-fluorophenyl)-2-oxo-N-(4-phenylbutyl)-1,3-benzoxazole-3(2H)-carboxamide}
-
in vivo plasma pharmacokinetic profile in mice, overview
-
6-bromo-2-oxo-N-(4-phenylbutyl)-1,3-benzoxazole-3(2H)-carboxamide
6-chloro-N-hexyl-2,4-dioxo-3,4-dihydropyrimidine-1(2H)-carboxamide
-
-
ACER2-specific siRNA
-
-
-
beta-D-octyl glucoside
-
almost complete inhibition at 1.5% (v/v)
C16-ceramide
-
ceramide synthesis activity, 10 mol%, 50% inhibition
C18-ceramine
-
mtCDase, competitive inhibition, IC50: 0.62 mol%
-
cardiolipin
-
inhibits the ceramide synthesis activity: total inhibition at 2.5-5 mol%, activates the ceramidase activity, mechanism
carmofur
CDase specific RNAi
-
-
-
Ceranib-1
-
i.e. 3-(3-(4-methoxyphenyl)acryloyl)-6-methyl-4-phenylquinolin-2(1H)-one
Ceranib-2
-
i.e. 3-[3-(4-methoxyphenyl)acryloyl]-4-phenyl-1H-quinolin-2-one
CHAPS
cholesterol
-
0.08 mM or below, decreases the hydrolysis of ceramide by a maximum of two-thirds
cis-D-erythro-sphingosine
-
mtCDase, weak inhibition
CuCl2
-
ceramide synthesis activity, 1 mM, total inhibition
D-erythro-2-(N-myristoylamino)-1-phenyl-1-propanol
D-erythro-dehydrosphingosine
-
mtCDase, IC50: 0.25 mol%
D-erythro-sphinganine
-
mtCDase, IC50: 0.2 mol%
D-erythro-sphingosine
D-erythro-urea-C16-ceramide
-
mtCDase, competitive inhibition, IC50: 0.33 mol%
-
D-NMAPPD
-
-
D-threo-ceramide
-
mt-CDase, IC50: 0.21 mol%
-
desipramine
di-isopropyl fluorophosphate
dihydrosphingosine
-
inhibits enzyme activity by up to 40% at 0.25 mM
dithiothreitol
DL-sphinganine
recombinant CDase
ethyl 5-fluoro-3-(hexylcarbamoyl)-2,6-dioxopyrimidine-1-carboxylate
-
-
fatty acids
-
-
Fe3+
-
almost complete inhibition at 10 mM
gemcitabine
-
-
glycodeoxycholate
isobutyl 5-fluoro-3-(hexylcarbamoyl)-2,6-dioxopyrimidine-1-carboxylate
-
-
L-erythro-ceramide
-
mt-CDase, IC50: 0.26 mol%
-
L-erythro-sphingosine
L-threo-ceramide
-
mt-CDase, IC50: 0.11 mol%
-
laureate
-
at pH 5
LCL385
LCL521
-
a lysosomotropic prodrug inhibitor of acid ceramidase, inhibition in vivo leads to decreased cell viability
-
lysophosphatidic acid
-
isoenzyme I only
lysophosphatidylcholine
-
ceramide synthesis activity, 10 mol%, moderate inhibition
methyl 5-fluoro-3-(hexylcarbamoyl)-2,6-dioxopyrimidine-1-carboxylate
-
-
methyl 5-fluoro-3-(octylcarbamoyl)-2,6-dioxopyrimidine-1-carboxylate
-
-
myristaldehyde
-
competitively inhibits the ceramide synthesis activity, 2.5-3 mol%, about 50% inhibition
N,N-dimethyl-D-erythro-sphingosine
-
mtCDase, weak inhibition
N-(2-hydroxy-2-phenylethyl)dodecane-1-sulfonamide
-
;
N-(2-hydroxy-2-phenylethyl)tetradecanamide
N-acetylcysteine
-
-
N-bromosuccinimide
-
modification of Trp completely inhibits forward and reverse reaction
N-butyl-2,4-dioxopyrimidine-1-carboxamide
-
-
N-heptyl-2,4-dioxopyrimidine-1-carboxamide
-
-
N-hexyl-2,4-dioxo-3,4-dihydropyrimidine-1(2H)-carboxamide
-
-
N-hexyl-2,4-dioxo-5-(trifluoromethyl)-3,4-dihydropyrimidine-1(2H)-carboxamide
-
-
N-hexyl-2,4-dioxo-5-phenylpyrimidine-1-carboxamide
-
-
N-hexyl-2,4-dioxo-pyrimidine-1-carboxamide
N-hexyl-2,4-dioxohexahydropyrimidine-1-carboxamide
-
-
N-hexyl-3-methyl-2,4-dioxopyrimidine-1-carboxamide
-
-
N-hexyl-5,6-dimethyl-2,4-dioxo-3,4-dihydropyrimidine-1(2H)-carboxamide
-
-
N-hexyl-5-(4-methylpiperazin-1-yl)-2,4-dioxopyrimidine-1-carboxamide
-
-
N-hexyl-5-(hydroxymethyl)-2,4-dioxopyrimidine-1-carboxamide
-
-
N-hexyl-5-bromo-2,4-dioxopyrimidine-1-carboxamide
-
-
N-hexyl-5-iodo-2,4-dioxopyrimidine-1-carboxamide
-
-
N-hexyl-5-methoxy-2,4-dioxopyrimidine-1-carboxamide
-
-
N-hexyl-5-methyl-2,4-dioxo-3,4-dihydropyrimidine-1(2H)-carboxamide
-
-
N-hexyl-5-methyl-2,4-dioxo-pyrimidine-1-carboxamide
N-hexyl-5-methylamino-2,4-dioxopyrimidine-1-carboxamide
-
-
N-hexyl-5-morpholino-2,4-dioxopyrimidine-1-carboxamide
-
-
N-hexyl-N-methyl-2,4-dioxopyrimidine-1-carboxamide
-
-
N-methyl-D-erythro-sphingosine
-
mtCDase, IC50: 0.13 mol%
N-nonyl-2,4-dioxopyrimidine-1-carboxamide
-
-
N-octyl-2,4-dioxo-5-(trifluoromethyl)pyrimidine-1-carboxamide
-
-
N-octyl-2,4-dioxopyrimidine-1-carboxamide
-
-
N-oleoylethanolamine
N-oleylethanolamine
-
-
N-pentyl-2,4-dioxopyrimidine-1-carboxamide
-
-
N-[(1R,2R)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]-12-(dimethylamino)dodecanamide
-
-
N-[(1R,2R)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]dodecane-1-sulfonamide
-
;
N-[(1R,2R)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]tridecan-1-aminium chloride
-
-
N-[(1R,2R)-1,3-dihydroxy-1-phenylpropan-2-yl]tridecan-1-aminium chloride
-
-
N-[(1R,2S)-1-hydroxy-1-phenylpropan-2-yl]-12-(1-methylhydrazinyl)dodecanamide
-
-
N-[(1S,2R)-1-hydroxy-1-(4-nitrophenyl)propan-2-yl]dodecane-1-sulfonamide
-
;
N-[(2R)-2-hydroxy-2-(4-methylphenyl)ethyl]tetradecanamide
-
;
N-[(2R)-2-hydroxy-2-(pyridin-3-yl)ethyl]-12-(1-methylhydrazinyl)dodecanamide
-
-
N-[(2R)-2-hydroxy-2-(pyridin-4-yl)ethyl]-12-(1-methylhydrazinyl)dodecanamide
-
-
N-[(2S 3R)-1,3-dihydroxyoctadecan-2-yl]3-methyl-2-butenamide.
-
-
N-[(2S)-2-hydroxy-2-(4-methylphenyl)ethyl]tetradecanamide
-
;
N-[(2S,3R)-1,3-dihydroxyoctadecan-2-yl]2,2-dibromoacetamide
-
strong inhibition
N-[(2S,3R)-1,3-dihydroxyoctadecan-2-yl]2-bromoacetamide
-
strong inhibition
N-[(2S,3R)-1,3-dihydroxyoctadecan-2-yl]2-methylacrylamide
-
strong inhibition
N-[(2S,3R)-1,3-dihydroxyoctadecan-2-yl]acrylamide
-
-
N-[2-(4-butylphenyl)-2-hydroxyethyl]tetradecanamide
-
;
N-[2-(4-ethylphenyl)-2-hydroxyethyl]tetradecanamide
-
;
N-[2-(4-fluorophenyl)-2-hydroxyethyl]tetradecanamide
-
;
N-[2-(4-tert-butylphenyl)-2-hydroxyethyl]tetradecanamide
-
;
N-[2-hydroxy-2-(3-hydroxyphenyl)ethyl]tetradecanamide
-
;
N-[2-hydroxy-2-(3-methoxyphenyl)ethyl]tetradecanamide
-
;
N-[2-hydroxy-2-(3-methylphenyl)ethyl]tetradecanamide
-
;
N-[2-hydroxy-2-(4-hydroxyphenyl)ethyl]tetradecanamide
-
;
N-[2-hydroxy-2-(4-methoxyphenyl)ethyl]tetradecanamide
-
;
N-[2-hydroxy-2-(4-methylphenyl)ethyl]dodecane-1-sulfonamide
-
;
N-[2-hydroxy-2-(4-methylphenyl)ethyl]tetradecanamide
-
;
N-[2-hydroxy-2-(4-propylphenyl)ethyl]tetradecanamide
-
;
N-[2-hydroxy-2-(pyridin-3-yl)ethyl]-12-(1-methylhydrazinyl)dodecanamide
-
-
N-[2-hydroxy-2-(pyridin-3-yl)ethyl]dodecane-1-sulfonamide
-
;
N-[2-hydroxy-2-(pyridin-3-yl)ethyl]tetradecanamide
-
-
N-[2-hydroxy-2-(pyridin-4-yl)ethyl]dodecane-1-sulfonamide
-
;
N-[2-hydroxy-2-(pyridin-4-yl)ethyl]tetradecanamide
NCDase siRNA
-
-
-
oleoylethanolamide
palmitaldehyde
-
ceramide synthesis activity, 2.5-3 mol%, about 50% inhibition
palmitate
-
at pH 5
phorbol myristate acetate
-
phorbol myristate acetate, PMA, decreases the expression of ACER2 in HeLa cells
phosphate
80% inhibition at 100 mM
phosphatidic acid
phosphatidylcholine
phosphatidylglycerol
-
ceramide synthesis activity, 10 mol%, moderate inhibition
phosphatidylserine
phytosphingosine
siRNA
-
Sn2+
-
at 10 mM
sodium cholate
-
ceramide synthesis
sphinganine
sphingenine
-
-
sphingomyelin
sphingosine
taurocholate
taurodeoxycholate
Triton X-100
urea-hexanoyl-ceramide
ZnCl2
-
ceramide synthesis activity, 1 mM, total inhibition
additional information
-