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ceramide + H2O
sphingosine + fatty acid
-
-
-
?
D-erythro-C12-NBD-ceramide + H2O
D-erythro-sphingosine + 4-nitrobenzo-2-oxa-1,3-diazoyl-dodecanoic acid
maCER1 has a highly restricted substrate specificity, maCER1 has a major ceramidase activity and only a very minor reverse activity
-
-
r
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
?
-
-
-
ir
4-nitrobenzo-2-oxa-1,3-diazole-C12-ceramide + H2O
4-nitrobenzo-2-oxa-1,3-diazole-dodecanoic acid + ceramide
-
-
-
-
?
4-nitrobenzo-2-oxa-1,3-diazole-N-dodecanoylsphingosine + H2O
?
-
-
-
-
?
4-nitrobenzo-2-oxa-1,3-diazole-N-hexanoylsphingosine + H2O
?
-
-
-
-
?
C12-4-nitrobenzo-2-oxa-1,3-diazole-ceramide + H2O
?
-
-
-
-
?
C16-14C-ceramide + H2O
?
-
-
-
-
?
C5-ceramide + H2O
valerate + sphingosine
-
-
-
?
ceramide + H2O
sphingosine + fatty acid
D-erythro-C12-NBD-ceramide + H2O
D-erythro-sphingosine + 4-nitrobenzo-2-oxa-1,3-diazoyl-dodecanoic acid
-
substrate in activity assay
-
-
?
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
-
-
-
-
r
N-acyl-sphingosine + H2O
a carboxylate + sphingosine
N-acylsphingosine + H2O
carboxylate + sphingosine
the carboxylate is a fatty acid
-
-
?
N-laurylsphingosine + H2O
laureate + sphingosine
-
-
-
-
?
N-oleoyl-D-erythro-ceramide + H2O
oleate + D-erythro-sphingosine
N-palmitoyl-D-erythro-sphingosine + H2O
D-erythro-sphingosine + palmitic acid
-
-
-
-
?
N-palmitoylphytosphingosine + H2O
?
-
-
-
-
?
N-palmitoylsphinganine + H2O
palmitic acid + sphinganine
-
-
-
-
?
N-palmitoylsphingosine + H2O
palmitic acid + sphingosine
-
-
-
-
?
N-stearoylphytosphingosine + H2O
?
-
-
-
-
?
N-stearoylsphinganine + H2O
stearic acid + sphinganine
-
-
-
-
?
N-stearoylsphingosine + H2O
stearic acid + sphingosine
-
-
-
-
?
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
?
fluorescently labelled ceramide analogue, 5.8% hydrolýsis
-
-
ir
octanoyl-D-erythro-sphingosine + H2O
?
-
substrate activity assay
-
-
?
palmitoyl-D-[erythro-9,10]sphingosine + H2O
palmitate + D-erythro-sphingosine
-
-
-
-
?
additional information
?
-
ceramide + H2O
sphingosine + fatty acid
-
-
-
-
?
ceramide + H2O
sphingosine + fatty acid
-
-
-
-
r
ceramide + H2O
sphingosine + fatty acid
-
-
-
?
N-acyl-sphingosine + H2O
a carboxylate + sphingosine
-
-
-
-
?
N-acyl-sphingosine + H2O
a carboxylate + sphingosine
-
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-oleoyl-D-erythro-ceramide + H2O
oleate + D-erythro-sphingosine
-
common substrate in erythrocytes
-
-
?
N-oleoyl-D-erythro-ceramide + H2O
oleate + D-erythro-sphingosine
-
i.e. D-e-C18:1-ceramide, common substrate in erythrocytes
-
-
?
additional information
?
-
maCER1 may play a role in regulating the levels of bioactive lipids ceramide and sphingosine-1-phosphate, as well as complex sphingolipids, maCER1 may have a specific role in skin function
-
-
?
additional information
?
-
-
maCER1 may play a role in regulating the levels of bioactive lipids ceramide and sphingosine-1-phosphate, as well as complex sphingolipids, maCER1 may have a specific role in skin function
-
-
?
additional information
?
-
not: D-erythro-C12-NBD-dihydroceramide, D-ribo-C12-NBD-phytoceramide, L-threo-C12-NBD-ceramide
-
-
?
additional information
?
-
-
not: D-erythro-C12-NBD-dihydroceramide, D-ribo-C12-NBD-phytoceramide, L-threo-C12-NBD-ceramide
-
-
?
additional information
?
-
-
acid ceramidase, but not acid sphingomyelinase, is required for tumor necrosis factor-alpha-induced prostaglandin PGE2 production, overview
-
-
?
additional information
?
-
-
the enzyme is involved in ceramide metabolism at the plasma membrane and in extracellular milieu, hydrolysis of ceramide on the cell surface, overview, involvement of the enzyme in stimulus-induced Cer metabolism by doxorubicin
-
-
?
additional information
?
-
-
the enzyme is involved in degradation of epidermal ceramides, ceramidase activity is not age-dependent
-
-
?
additional information
?
-
-
ceramidase catalyzes the hydrolysis of ceramide to form sphingosine and free fatty acid
-
-
?
additional information
?
-
-
cleaves the N-acyl linkage of ceramides into a sphingosine base and a free fatty acid
-
-
?
additional information
?
-
the N-acyl moiety of ceramide is cleaved by ceramidases to form the lysolipid sphingosine that undergoes further phosphorylation to sphingosine-1-phosphate
-
-
?
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ceramide + H2O
sphingosine + fatty acid
-
-
-
?
ceramide + H2O
sphingosine + fatty acid
N-acyl-sphingosine + H2O
a carboxylate + sphingosine
-
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
carboxylate + sphingosine
the carboxylate is a fatty acid
-
-
?
N-oleoyl-D-erythro-ceramide + H2O
oleate + D-erythro-sphingosine
-
common substrate in erythrocytes
-
-
?
additional information
?
-
ceramide + H2O
sphingosine + fatty acid
-
-
-
-
?
ceramide + H2O
sphingosine + fatty acid
-
-
-
-
r
ceramide + H2O
sphingosine + fatty acid
-
-
-
?
additional information
?
-
maCER1 may play a role in regulating the levels of bioactive lipids ceramide and sphingosine-1-phosphate, as well as complex sphingolipids, maCER1 may have a specific role in skin function
-
-
?
additional information
?
-
-
maCER1 may play a role in regulating the levels of bioactive lipids ceramide and sphingosine-1-phosphate, as well as complex sphingolipids, maCER1 may have a specific role in skin function
-
-
?
additional information
?
-
-
acid ceramidase, but not acid sphingomyelinase, is required for tumor necrosis factor-alpha-induced prostaglandin PGE2 production, overview
-
-
?
additional information
?
-
-
the enzyme is involved in ceramide metabolism at the plasma membrane and in extracellular milieu, hydrolysis of ceramide on the cell surface, overview, involvement of the enzyme in stimulus-induced Cer metabolism by doxorubicin
-
-
?
additional information
?
-
-
the enzyme is involved in degradation of epidermal ceramides, ceramidase activity is not age-dependent
-
-
?
additional information
?
-
-
ceramidase catalyzes the hydrolysis of ceramide to form sphingosine and free fatty acid
-
-
?
additional information
?
-
-
cleaves the N-acyl linkage of ceramides into a sphingosine base and a free fatty acid
-
-
?
additional information
?
-
the N-acyl moiety of ceramide is cleaved by ceramidases to form the lysolipid sphingosine that undergoes further phosphorylation to sphingosine-1-phosphate
-
-
?
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Cu2+
1 mM, 60% inhibition, inhibits in a dose-dependent manner
Mn2+
1 mM, 10% inhibition, inhibits in a dose-dependent manner
sphingosine
product inhibition in a dose-dependent manner, IC50: 0.08 mM
Zn2+
1 mM, 60% inhibition, inhibits in a dose-dependent manner
(1R,2R)-2-N-myristoylamino-1-(4-nitrophenyl)-1,3-propandiol
-
-
(1S,2R)-2-N-myristoylamino-1-phenyl-1-propanol
-
-
(1S,2R)-D-erythro-2-(N-myristoylamino)-1-phenyl-1-propanol
-
i.e. D-e-MAPP, an alkaline ceramidase inhibitor, that potently and specifically inhibits ACER activity
1-hexylcarbamoyl-5-fluorouracil
i.e. carmofur
1R,2R-(2-N-myristoylamino-1-(4-nitrophenyl)-1,3-dihydroxypropane)
-
-
1S,2S-(2-N-myristoylamino-1-(4-nitrophenyl)-1,3-dihydroxypropane)
-
-
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
-
D-erythro-2-(N-myristoylamino)-1-phenyl-1-propanol
-
inhibitor of alkaline ceramidase
urea-hexanoyl-ceramide
-
-
N-oleoylethanolamine
-
-
N-oleoylethanolamine
-
inhibitor of acid ceramidase
additional information
not inhibited by Mg2+, phytosphingosine, dihydrosphingosine
-
additional information
-
not inhibited by Mg2+, phytosphingosine, dihydrosphingosine
-
additional information
-
desipramine downregulates the enzyme in fibroblasts
-
additional information
a class of benzoxazolone carboxamides act as the first potent and systemically active inhibitors of the acid ceramidase. Prototype members of this class inhibit the enzyme with low nanomolar potency by covalent binding to the catalytic cysteine. No inhibition by N-methyl-2-oxo-N-(4-phenylbutyl)-1,3-benzoxazole-3(2H)-carboxamide, 4-phenylbutyl 2-oxo-1,3-benzoxazole-3(2H)-carboxylate, and 3-(6-phenylhexanoyl)-1,3-benzoxazol-2(3H)-one, while 2-oxo-N-(4-phenylbutyl)-1,3-benzoxazole-3(2H)-carbothioamide is unstable
-
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0.000000053
-
homozygous F508del mice, lung
0.000000055
-
wild-type mice, lung
0.000000056
-
heterozygous F508del mice, lung
0.0000028
-
homozygous F508del mice, spleen
0.0000035
-
wild-type mice, lung
0.00000375
-
heterozygous F508del mice, lung
0.00000416
-
homozygous F508del mice, lung
0.00001
-
homozygous F508del mice, mucosal homogenates
0.0000127
-
heterozygous F508del mice, mucosal homogenates
0.0000137
-
heterozygous F508del mice, mucosal homogenates
0.0000145
-
homozygous F508del mice, mucosal homogenates
0.0000155
-
wild-type mice, mucosal homogenates
0.0000163
-
wild-type mice, mucosal homogenates
0.0000167
-
wild-type mice, mucosal homogenates
0.0000187
-
wild-type mice, kidney
0.0000188
-
heterozygous F508del mice, mucosal homogenates
0.0000192
-
homozygous F508del mice, mucosal homogenates
0.0000193
-
homozygous F508del mice, kidney
0.00002
-
homozygous F508del mice, mucosal homogenates
0.0000215
-
wild-type mice, liver
0.0000227
-
heterozygous F508del mice, mucosal homogenates
0.000023
-
wild-type mice, mucosal homogenates
0.0000238
-
homozygous F508del mice, liver
0.0000255
-
heterozygous F508del mice, liver
0.0000272
-
heterozygous F508del mice, mucosal homogenates
0.0000273
-
wild-type mice, mucosal homogenates
0.0000292
-
homozygous F508del mice, mucosal homogenates
0.0000308
-
heterozygous F508del mice, mucosal homogenates
0.0000417
-
wild-type mice, mucosal homogenates
0.000048
-
wild-type mice, mucosal homogenates
0.0000542
-
homozygous F508del mice, mucosal homogenates
0.0000625
-
heterozygous F508del mice, mucosal homogenates
0.0001
-
heterozygous F508del mice, mucosal homogenates
additional information
-
determination of sphingolipid levels by mass spectrometry
0.000002
-
heterozygous F508del mice, spleen
0.000002
-
wild-type mice, spleen
0.0000208
-
heterozygous F508del mice, kidney
0.0000208
-
homozygous F508del mice, mucosal homogenates
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additional information
enzyme structure-function relationship, overview. The enzyme contains a signal/anchor sequence and a mucin box
evolution
ceramidases are classified into three distinct groups, acid (Asah1), neutral (Asah2), and alkaline (Asah3) CDases, based on their primary structure and optimum pH. Acid CDase catabolizes ceramide in lysosomes and is found only in vertebrates. In contrast, the distribution of neutral and alkaline CDases is broad, with both being found in species ranging from lower eukaryotes to mammals; however, only neutral CDase is found in prokaryotes, including some pathogenic bacteria. Neutral CDase is thought to have gained a specific domain (mucin box) in the N-terminal region after the vertebrate split, allowing the enzyme to be stably expressed at the plasmamembrane as a type II membrane protein. Molecular evolution of neutral ceramidase acquiring a mucin box, overview
evolution
distant homologues from nCDase are found in taxa all over evolution reinforcing a crucial role for ceramide
malfunction
-
inhibition of acid ceramidase activity stimulates apoptotic cell death. Point mutations in the acid ceramidase gene cause rare autosomal recessive Farber disease. Homozygous acid ceramidase-deficient mice are embryonic lethal
malfunction
KO mice are impaired in the intestinal degradation of sphingolipids
malfunction
genetic loss or inhibition of acid ceramidase prevents formation of glycosphingoid bases
malfunction
nCDase deficient mice are viable with no obvious deficiency under normal breeding conditions. Further investigation reveals that nCDase deficient mice are not able to degrade dietary sphingolipids. Gemcitabine treated cells show an increase of the levels of specific ceramides, attributed to a reduction of nCDase expression. The increased ceramide is also implicated in suppression of cell growth. nCDase deficient mice treated with DSS show a paradoxical elevation of sphingosine and an increase of sphingosine 1-phosphate. Knockout mice are partly protected from brain injury. MEFs from nCDase deficient mice present an increase of autophagic flux and more specifically mitophagy when subjected to the 2DG/AA model of necroptosis. They showed as well that inhibition of autophagy reverses this phenotype. Inhibition of nCDase may enhance cell survival by increasing the clearance of damaged mitochondria via mitophagy
physiological function
-
alkaline ceramidases have a compensatory role in controlling sphingosine and sphingosine 1-phosphate generation in erythroid cells
physiological function
-
neutral ceramidase is a key participant of ceramide formation in liver mitochondria. The reverse activity of neutral ceramidase contributes to sphingolipid homeostasis in this organelle in vivo. The enzyme contributes to the overall ceramide profile of liver mitochondria at basal conditions in vivo
physiological function
ceramide hydrolysis by acid ceramidase stops the biological activity of ceramides and influences survival and function of normal and neoplastic cells
physiological function
neutral CDase may be involved in a pathway for the digestion of dietary sphingolipids in mice
physiological function
acid ceramidase actively forms glycosphingoid bases in Gaucher and Fabry disease. Molecular basis of the formation of glucosylsphingosine and globotriaosylsphingosine during deficiency of glucocerebrosidase (Gaucher disease) and alpha-galactosidase A (Fabry disease), active role of acid ceramidase in both processes through deacylation of lysosomal glycosphingolipids, overview. Possibility of broadened substrate specificity of acid ceramidase during lysosomal lipid accumulation
physiological function
nCDase regulates the levels of bioactive sphingolipid metabolites in the intestinal tract. CDase may protect against inflammation using a dextran sodium sulfate (DSS) mouse model. Role of nCDase in traumatic brain injury
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Tani, M.; Okino, N.; Mitsutake, S.; Tanigawa, T.; Izu, H.; Ito, M.
Purification and characterization of a neutral ceramidase from mouse liver
J. Biol. Chem.
275
3462-3468
2000
Mus musculus
brenda
Mao, C.; Xu, R.; Szulc, Z.M.; Bielawski, J.; Becker, K.P.; Bielawska, A.; Galadari, S.H.; Hu, W.; Obeid, L.M.
Cloning and characterization of a mouse endoplasmic reticulum alkaline ceramidase. An enzyme that preferentially regulates metabolism of very long chain ceramides
J. Biol. Chem.
278
31184-31191
2003
Mus musculus (Q8R4X1), Mus musculus
brenda
Jensen, J.M.; Forl, M.; Winoto-Morbach, S.; Seite, S.; Schunck, M.; Proksch, E.; Schutze, S.
Acid and neutral sphingomyelinase, ceramide synthase, and acid ceramidase activities in cutaneous aging
Exp. Dermatol.
14
609-618
2005
Mus musculus
brenda
Tani, M.; Igarashi, Y.; Ito, M.
Involvement of neutral ceramidase in ceramide metabolism at the plasma membrane and in extracellular milieu
J. Biol. Chem.
280
36592-36600
2005
Mus musculus
brenda
Zeidan, Y.H.; Pettus, B.J.; Elojeimy, S.; Taha, T.; Obeid, L.M.; Kawamori, T.; Norris, J.S.; Hannun, Y.A.
Acid ceramidase but not acid sphingomyelinase is required for tumor necrosis factor-{alpha}-induced PGE2 production
J. Biol. Chem.
281
24695-24703
2006
Mus musculus
brenda
Kono, M.; Dreier, J.L.; Ellis, J.M.; Allende, M.L.; Kalkofen, D.N.; Sanders, K.M.; Bielawski, J.; Bielawska, A.; Hannun, Y.A.; Proia, R.L.
Neutral ceramidase encoded by the Asah2 gene is essential for the intestinal degradation of sphingolipids
J. Biol. Chem.
281
7324-7331
2006
Mus musculus
brenda
Eliyahu, E.; Park, J.H.; Shtraizent, N.; He, X.; Schuchman, E.H.
Acid ceramidase is a novel factor required for early embryo survival
FASEB J.
21
1403-1409
2007
Mus musculus
brenda
Ohlsson, L.; Hjelte, L.; Huehn, M.; Scholte, B.J.; Wilke, M.; Flodstroem-Tullberg, M.; Nilsson, A.
Expression of intestinal and lung alkaline sphingomyelinase and neutral ceramidase in cystic fibrosis f508del transgenic mice
J. Pediatr. Gastroenterol. Nutr.
47
547-554
2008
Mus musculus
brenda
Mao, C.; Obeid, L.M.
Ceramidases: regulators of cellular responses mediated by ceramide, sphingosine, and sphingosine-1-phosphate
Biochim. Biophys. Acta
1781
424-434
2008
Homo sapiens, Homo sapiens (Q5QJU3), Homo sapiens (Q8TDN7), Homo sapiens (Q9NR71), Homo sapiens (Q9NUN7), Mus musculus (Q8R4X1), Mus musculus (Q8VD53), Mus musculus (Q9D099), Mus musculus (Q9JHE3), Mus musculus (Q9WV54), Mus musculus
brenda
Wu, B.X.; Zeidan, Y.H.; Hannun, Y.A.
Downregulation of neutral ceramidase by gemcitabine: Implications for cell cycle regulation
Biochim. Biophys. Acta
1791
730-739
2009
Mus musculus
brenda
Houben, E.; Hachem, J.P.; De Paepe, K.; Rogiers, V.
Epidermal ceramidase activity regulates epidermal desquamation via stratum corneum acidification
Skin Pharmacol. Physiol.
21
111-118
2008
Mus musculus
brenda
Xu, R.; Sun, W.; Jin, J.; Obeid, L.M.; Mao, C.
Role of alkaline ceramidases in the generation of sphingosine and its phosphate in erythrocytes
FASEB J.
24
2507-2515
2010
Homo sapiens, Mus musculus
brenda
Novgorodov, S.A.; Wu, B.X.; Gudz, T.I.; Bielawski, J.; Ovchinnikova, T.V.; Hannun, Y.A.; Obeid, L.M.
Novel pathway of ceramide production in mitochondria: thioesterase and neutral ceramidase produce ceramide from sphingosine and acyl-CoA
J. Biol. Chem.
286
25352-25362
2011
Mus musculus, Rattus norvegicus
brenda
Park, J.; Yoon, S.
Ceramide, a crucial functional lipid, and its metabolic regulation by acid ceramidase
Food Sci. Biotechnol.
19
859-864
2010
Homo sapiens, Mus musculus
-
brenda
Pizzirani, D.; Bach, A.; Realini, N.; Armirotti, A.; Mengatto, L.; Bauer, I.; Girotto, S.; Pagliuca, C.; De Vivo, M.; Summa, M.; Ribeiro, A.; Piomelli, D.
Benzoxazolone carboxamides: potent and systemically active inhibitors of intracellular acid ceramidase
Angew. Chem. Int. Ed. Engl.
54
485-489
2015
Homo sapiens (Q13510), Mus musculus (Q9WV54)
brenda
Ito, M.; Okino, N.; Tani, M.
New insight into the structure, reaction mechanism, and biological functions of neutral ceramidase
Biochim. Biophys. Acta
1841
682-691
2014
Dictyostelium discoideum, Mycobacterium tuberculosis, Oryza sativa, Pseudomonas aeruginosa, Tribolium castaneum, Dermatophilus congolensis, Triticum aestivum (A9YFM2), Aspergillus oryzae (Q5B5D5), Danio rerio (Q5W7F1), Rattus norvegicus (Q91XT9), Mus musculus (Q9JHE3), Homo sapiens (Q9NR71), Drosophila melanogaster (Q9VA70), Laodelphax striatellus (R4N4U2)
brenda
Bhabak, K.P.; Hauser, A.; Redmer, S.; Banhart, S.; Heuer, D.; Arenz, C.
Development of a novel FRET probe for the real-time determination of ceramidase activity
ChemBioChem
14
1049-1052
2013
Homo sapiens (Q9NR71), Mus musculus (Q9WV54)
brenda
Coant, N.; Hannun, Y.A.
Neutral ceramidase advances in mechanisms, cell regulation, and roles in cancer
Adv. Biol. Regul.
71
141-146
2019
Nilaparvata lugens, Amorphophallus muelleri (A0A2D1WBF2), Rattus norvegicus (Q91XT9), Mus musculus (Q9JHE3), Homo sapiens (Q9NR71)
brenda
Ferraz, M.J.; Marques, A.R.; Appelman, M.D.; Verhoek, M.; Strijland, A.; Mirzaian, M.; Scheij, S.; Ouairy, C.M.; Lahav, D.; Wisse, P.; Overkleeft, H.S.; Boot, R.G.; Aerts, J.M.
Lysosomal glycosphingolipid catabolism by acid ceramidase formation of glycosphingoid bases during deficiency of glycosidases
FEBS Lett.
590
716-725
2016
Homo sapiens (Q13510), Homo sapiens, Mus musculus (Q9WV54)
brenda