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C17-ceramide + 1,2-dimyristoyl-rac-glycero-3-phosphocholine
C17-sphingomyelin + 1,2-dimyristoyl-rac-glycerol
-
-
-
?
L-alpha-phosphatidylcholine + NBD-C6-ceramide
?
i.e. N-(6-[(7-nitro-benz-2-oxa-1,3-diazo-4-yl)amino]caproyl)-ceramide
-
-
?
phosphatidylcholine + C6-ceramide
C6-sphingomyelin + 1,2-diacyl-sn-glycerol
-
-
-
?
phosphatidylcholine + C8-ceramide
C7-sphingomyelin + 1,2-diacyl-sn-glycerol
-
-
-
?
phosphatidylcholine + ceramide
sphingomyelin + 1,2-diacyl-sn-glycerol
-
-
-
?
a ceramide + a phosphatidylcholine
a sphingomyelin + a 1,2-diacyl-sn-glycerol
C17-ceramide + 1,2-dimyristoyl-rac-glycero-3-phosphocholine
C17-sphingomyelin + 1,2-dimyristoyl-rac-glycerol
-
-
-
?
ceramide + phosphatidylcholine
sphingomyelin + 1,2-diacyl-sn-glycerol
L-alpha-phosphatidylcholine + N-(6-[(7-nitro-benz-2-oxa-1,3-diazo-4-yl)amino]caproyl)-ceramide
?
-
i.e. NBD-C6-ceramide
-
-
?
L-alpha-phosphatidylcholine + NBD-C6-ceramide
?
i.e. N-(6-[(7-nitro-benz-2-oxa-1,3-diazo-4-yl)amino]caproyl)-ceramide
-
-
?
phosphatidylcholine + C6-ceramide
?
-
-
-
-
?
phosphatidylcholine + C6-ceramide
C6-sphingomyelin + 1,2-diacyl-sn-glycerol
phosphatidylcholine + C6-NBD-ceramide
?
-
i.e. N-[6-[(7-nitro-2-1,3-benzoxadiazol-4-yl)amino]hexanoyl]-D-erythro-sphingosine, the fluorogenic derivative of C6-ceramide
-
-
?
phosphatidylcholine + C8-ceramide
C7-sphingomyelin + 1,2-diacyl-sn-glycerol
-
-
-
?
phosphatidylcholine + ceramide
sphingomyelin + 1,2-diacyl-sn-glycerol
additional information
?
-
a ceramide + a phosphatidylcholine
a sphingomyelin + a 1,2-diacyl-sn-glycerol
-
-
-
?
a ceramide + a phosphatidylcholine
a sphingomyelin + a 1,2-diacyl-sn-glycerol
-
-
-
-
?
a ceramide + a phosphatidylcholine
a sphingomyelin + a 1,2-diacyl-sn-glycerol
-
-
-
r
a ceramide + a phosphatidylcholine
a sphingomyelin + a 1,2-diacyl-sn-glycerol
substrate C6-NBD-ceramide, molecular docking studies and interaction modes of phosphatidylcholine with the active site of SMS1, overview
detection and quantifcation of C6-NBD-sphingomyelin by HPLC using the reversed-phase C18 column and an isocratic elution with methanol/water/trifluoroacetic acid (89:11:0.1 (v/v))
-
?
ceramide + phosphatidylcholine
sphingomyelin + 1,2-diacyl-sn-glycerol
-
-
-
-
?
ceramide + phosphatidylcholine
sphingomyelin + 1,2-diacyl-sn-glycerol
-
the enzyme restores homeostasis between sphingomyelin and ceramide pools
-
-
?
phosphatidylcholine + C6-ceramide
C6-sphingomyelin + 1,2-diacyl-sn-glycerol
-
-
-
-
?
phosphatidylcholine + C6-ceramide
C6-sphingomyelin + 1,2-diacyl-sn-glycerol
-
-
-
?
phosphatidylcholine + ceramide
sphingomyelin + 1,2-diacyl-sn-glycerol
-
-
-
-
?
phosphatidylcholine + ceramide
sphingomyelin + 1,2-diacyl-sn-glycerol
-
-
-
?
phosphatidylcholine + ceramide
sphingomyelin + 1,2-diacyl-sn-glycerol
-
-
-
?
additional information
?
-
sphingomyelin synthase sits at the crossroads of sphingomyelin, ceramide, and diacylglycerol metabolism. It utilizes ceramide and phosphatidylcholine as substrates to produce sphingomyelin and diacylglycerol, thereby regulating lipid messengers which play a role in cell survival and apoptosis
-
-
?
additional information
?
-
sphingomyelin synthase sits at the crossroads of sphingomyelin, ceramide, and diacylglycerol metabolism. It utilizes ceramide and phosphatidylcholine as substrates to produce sphingomyelin and diacylglycerol, thereby regulating lipid messengers which play a role in cell survival and apoptosis
-
-
?
additional information
?
-
-
both sphingomyelin synthases SMS1 and SMS2 are required for sphingomyelin homeostasis and growth in human HeLa cells, sphingomyelin synthesis plays a critical role in cell growth and survival, overview
-
-
?
additional information
?
-
-
membrane sphingomyelin is a key component of lipid rafts involved in TCR signal transduction, physiological functions of sphingomyelin, overview
-
-
?
additional information
?
-
-
SMS1 converts de novo ceramide into sphingomyelin, overview
-
-
?
additional information
?
-
-
SMS1 suppresses ceramide production and apoptosis post-photodamage
-
-
?
additional information
?
-
-
SMS2 regulates sphingomyelin levels in plasma membrane and lipid rafts and has a potential to regulate NFkappaB activation, via multiple mechanisms, overview
-
-
?
additional information
?
-
-
sphingomyelin plays a very important role both in cell membrane formation, inhibition of sphingomyelin synthase affects intracellular sphingomyelin accumulation and plasma membrane lipid organization, overview
-
-
?
additional information
?
-
sphingomyelin synthase sits at the crossroads of sphingomyelin, ceramide, and diacylglycerol metabolism. It utilizes ceramide and phosphatidylcholine as substrates to produce sphingomyelin and diacylglycerol, thereby regulating lipid messengers which play a role in cell survival and apoptosis
-
-
?
additional information
?
-
sphingomyelin synthase sits at the crossroads of sphingomyelin, ceramide, and diacylglycerol metabolism. It utilizes ceramide and phosphatidylcholine as substrates to produce sphingomyelin and diacylglycerol, thereby regulating lipid messengers which play a role in cell survival and apoptosis
-
-
?
additional information
?
-
-
sphingomyelin synthases regulate production of diacylglycerol at the Golgi apparatus. Downregulation or up-regulation of SMS1 or SMS2 reduces or enhances de novo synthesis of sphingomyelin, pathway regulation, overview
-
-
?
additional information
?
-
-
SMSr proteins display ceramide phosphoethanolamine synthase activity, SMSr produces only trace amounts of ceramide phosphoethanolamine, i.e., 300fold less than SMS1-derived sphingomyelin
-
-
?
additional information
?
-
-
sphingomyelin synthase SMS2 displays dual activity as ceramide phosphoethanolamine synthase
-
-
?
additional information
?
-
sphingomyelin measurement via a four-step enzymatic process involving sphingomyelinase and histochemic detection
-
-
?
additional information
?
-
-
sphingomyelin measurement via a four-step enzymatic process involving sphingomyelinase and histochemic detection
-
-
?
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
phosphatidylcholine + ceramide
sphingomyelin + 1,2-diacyl-sn-glycerol
-
-
-
?
a ceramide + a phosphatidylcholine
a sphingomyelin + a 1,2-diacyl-sn-glycerol
ceramide + phosphatidylcholine
sphingomyelin + 1,2-diacyl-sn-glycerol
phosphatidylcholine + ceramide
sphingomyelin + 1,2-diacyl-sn-glycerol
-
-
-
?
additional information
?
-
a ceramide + a phosphatidylcholine
a sphingomyelin + a 1,2-diacyl-sn-glycerol
-
-
-
?
a ceramide + a phosphatidylcholine
a sphingomyelin + a 1,2-diacyl-sn-glycerol
-
-
-
-
?
a ceramide + a phosphatidylcholine
a sphingomyelin + a 1,2-diacyl-sn-glycerol
-
-
-
r
ceramide + phosphatidylcholine
sphingomyelin + 1,2-diacyl-sn-glycerol
-
-
-
-
?
ceramide + phosphatidylcholine
sphingomyelin + 1,2-diacyl-sn-glycerol
-
the enzyme restores homeostasis between sphingomyelin and ceramide pools
-
-
?
additional information
?
-
sphingomyelin synthase sits at the crossroads of sphingomyelin, ceramide, and diacylglycerol metabolism. It utilizes ceramide and phosphatidylcholine as substrates to produce sphingomyelin and diacylglycerol, thereby regulating lipid messengers which play a role in cell survival and apoptosis
-
-
?
additional information
?
-
sphingomyelin synthase sits at the crossroads of sphingomyelin, ceramide, and diacylglycerol metabolism. It utilizes ceramide and phosphatidylcholine as substrates to produce sphingomyelin and diacylglycerol, thereby regulating lipid messengers which play a role in cell survival and apoptosis
-
-
?
additional information
?
-
-
both sphingomyelin synthases SMS1 and SMS2 are required for sphingomyelin homeostasis and growth in human HeLa cells, sphingomyelin synthesis plays a critical role in cell growth and survival, overview
-
-
?
additional information
?
-
-
membrane sphingomyelin is a key component of lipid rafts involved in TCR signal transduction, physiological functions of sphingomyelin, overview
-
-
?
additional information
?
-
-
SMS1 converts de novo ceramide into sphingomyelin, overview
-
-
?
additional information
?
-
-
SMS1 suppresses ceramide production and apoptosis post-photodamage
-
-
?
additional information
?
-
-
SMS2 regulates sphingomyelin levels in plasma membrane and lipid rafts and has a potential to regulate NFkappaB activation, via multiple mechanisms, overview
-
-
?
additional information
?
-
-
sphingomyelin plays a very important role both in cell membrane formation, inhibition of sphingomyelin synthase affects intracellular sphingomyelin accumulation and plasma membrane lipid organization, overview
-
-
?
additional information
?
-
sphingomyelin synthase sits at the crossroads of sphingomyelin, ceramide, and diacylglycerol metabolism. It utilizes ceramide and phosphatidylcholine as substrates to produce sphingomyelin and diacylglycerol, thereby regulating lipid messengers which play a role in cell survival and apoptosis
-
-
?
additional information
?
-
sphingomyelin synthase sits at the crossroads of sphingomyelin, ceramide, and diacylglycerol metabolism. It utilizes ceramide and phosphatidylcholine as substrates to produce sphingomyelin and diacylglycerol, thereby regulating lipid messengers which play a role in cell survival and apoptosis
-
-
?
additional information
?
-
-
sphingomyelin synthases regulate production of diacylglycerol at the Golgi apparatus. Downregulation or up-regulation of SMS1 or SMS2 reduces or enhances de novo synthesis of sphingomyelin, pathway regulation, overview
-
-
?
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
1-methylcyclopropyl 4-(3-((3-((3,5-bis(trifluoromethyl)benzyl)(methyl)carbamoyl)-1-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-4-yl)oxy)propyl)piperidine-1-carboxylate
-
1-methylcyclopropyl 4-(3-((3-((3,5-bis(trifluoromethyl)benzyl)(methyl)carbamoyl)-1-methyl-2-oxo-1,2-dihydroquinolin-4-yl)oxy)propyl)piperidine-1-carboxylate
150fold selectivity for isoform SGMS2 over SGMS1. The interaction with SGMS2 requires the presence of the amino acids S227 and H229, which are located in the catalytic domain of SMS2
1-methylcyclopropyl 4-(3-((3-((3-methoxy-5-(trifluoromethyl)benzyl)(methyl)carbamoyl)-1-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-4-yl)oxy)propyl)piperidine-1-carboxylate
potent and selective inhibitor of isoform SGMS2. A repeated treatment in mice leads to significant reduction in hepatic sphingomyelin levels
2-((2,5-dichlorobenzyl)oxy)-N-(pyridin-3-yl)benzamide
-
2-((2,5-dimethoxybenzyl)oxy)-N-(pyridin-3-yl)benzamide
-
2-((2,6-dichlorobenzyl)oxy)-N-(pyridin-3-yl)benzamide
-
2-((2,6-dimethylbenzyl)oxy)-N-(pyridin-3-yl)benzamide
-
2-((2-((5-chloropentyl)oxy)benzyl)oxy)-N-(pyridin-3-yl)benzamide
-
2-((2-((6-chlorohexyl)oxy)benzyl)oxy)-N-(pyridin-3-yl)benzamide
-
2-((2-(4-chlorobutoxy)benzyl)oxy)-N-(pyridin-3-yl)benzamide
-
2-((2-chloro-5-fluorobenzyl)oxy)-N-(pyridin-3-yl)benzamide
-
2-((2-chloro-6-fluorobenzyl)oxy)-N-(pyridin-3-yl)benzamide
-
2-((2-chlorobenzyl)oxy)-N-(pyridin-3-yl)benzamide
-
2-((2-ethylbenzyl)oxy)-N-(pyridin-3-yl)benzamide
selectivity ratio is more than 1400fold for purified isoform SGMS2 over SGMS1. The compound dose-dependently diminishes apoB secretion from Huh7 cells, and significantly reduces the SGMS activity and increases cholesterol efflux from macrophages. It inhibits the secretion of LPS-mediated pro-inflammatory cytokine and chemokine in macrophages. In C57BL/6J mice, the compound is orally efficacious.
2-((2-fluorobenzyl)oxy)-N-(pyridin-3-yl)benzamide
-
2-((2-methylbenzyl)oxy)-N-(pyridin-3-yl)benzamide
-
2-((3-chloro-2-fluorobenzyl)oxy)-N-(pyridin-3-yl)benzamide
-
2-((3-chloro-2-methylbenzyl)oxy)-N-(pyridin-3-yl)benzamide
-
2-((3-chlorobenzyl)oxy)-N-(pyridin-3-yl)benzamide
-
2-((3-fluorobenzyl)oxy)-N-(pyridin-3-yl)benzamide
-
2-((5-chloro-2-(2-methoxyethoxy)benzyl)oxy)-N-(pyridin-3-yl)benzamide
-
2-((5-chloro-2-(3-methoxypropoxy)benzyl)oxy)-N-(pyridin-3-yl)benzamide
-
2-((5-chloro-2-(heptyloxy)benzyl)oxy)-N-(pyridin-3-yl)benzamide
-
2-((5-chloro-2-(hexyloxy)benzyl)oxy)-N-(pyridin-3-yl)benzamide
-
2-((5-chloro-2-methoxybenzyl)oxy)-N-(pyridin-3-yl)benzamide
-
2-((5-chloro-2-methylbenzyl)oxy)-N-(pyridin-3-yl)benzamide
-
2-((5-fluoro-2-methylbenzyl)oxy)-N-(pyridin-3-yl)benzamide
-
2-(benzyloxy)-N-(pyridin-2-yl)benzamide
-
2-(benzyloxy)-N-(pyridin-3-yl)benzamide
-
2-[2-[(2-methylphenyl)methoxy]phenyl][1,3]oxazolo[5,4-b]pyridine
-
2-[[2-((5-(3-(2-amino-2-oxoethyl)-5-methoxy-2-methyl-1H-indol-1-yl)pentyl)oxy)benzyl]oxy]-N-(pyridin-3-yl)benzamide
compound shows dual activity against both phospholipase A2 and sphingomyelin synthase
2-[[2-((6-(3-(2-amino-2-oxoethyl)-5-methoxy-2-methyl-1H-indol-1-yl)hexyl)oxy)benzyl]oxy]-N-(pyridin-3-yl)benzamide
-
2-[[2-(3-(3-(2-amino-2-oxoethyl)-5-methoxy-2-methyl-1H-indol-1-yl)propoxy)benzyl]oxy]-N-(pyridin-3-yl)benzamide
-
2-[[2-(4-(3-(2-amino-2-oxoethyl)-5-methoxy-2-methyl-1H-indol-1-yl)butoxy)benzyl]oxy]-N-(pyridin-3-yl)benzamide
-
4-(3-((3-((3,5-bis(trifluoromethyl)benzyl)(methyl)carbamoyl)-1-methyl-2-oxo-1,2-dihydroquinolin-4-yl)oxy)propyl)piperidine-1-carboxylate
-
4-(3-(benzyloxy)pyrrolidin-1-yl)-N-(3,5-bis(trifluoromethyl)benzyl)-N,1-dimethyl-2-oxo-1,2-dihydroquinoline-3-carboxamide
-
N-(3,5-bis(trifluoromethyl)benzyl)-N,1-dimethyl-2-oxo-4-((2-phenylpyridin-4-yl)methoxy)-1,2-dihydroquinoline-3-carboxamide
880fold selectivity for isoform SGMS2 over SGMS1
N-(3,5-bis(trifluoromethyl)benzyl)-N,1-dimethyl-2-oxo-4-(4,4,4-trifluorobutoxy)-1,2-dihydroquinoline-3-carboxamide
-
N-(3,5-bis(trifluoromethyl)benzyl)-N,1-dimethyl-2-oxo-4-(pyrrolidin-1-yl)-1,2-dihydroquinoline-3-carboxamide
more than 100fold selectivity for isoform SGMS2 over SGMS1
N-(pyridin-3-yl)-2-((2-(trifluoromethyl)benzyl)oxy)benzamide
-
N-[(4-bromophenyl)methyl]-2-[4-[(2-phenylethyl)sulfamoyl]phenoxy]acetamide
-
tert-butyl 4-(3-((3-((3,5-dimethoxybenzyl)(methyl)carbamoyl)-1-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-4-yl)oxy)propyl)piperidine-1-carboxylate
-
tert-butyl 4-(3-((3-((3,5-dimethoxybenzyl)(methyl)carbamoyl)-1-methyl-2-oxo-1,2-dihydroquinolin-4-yl)oxy)propyl)piperidine-1-carboxylate
-
tricyclodecan-9-yl-xanthogenate
i.e. D609
-
tricyclodecane-9-yl xanthogenate
i.e. D609
-
1-methylcyclopropyl 4-(3-((3-((3,5-bis(trifluoromethyl)benzyl)(methyl)carbamoyl)-1-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-4-yl)oxy)propyl)piperidine-1-carboxylate
inhibitor of isoform SGMS2 with good selectivity against SGMS1
1-methylcyclopropyl 4-(3-((3-((3,5-bis(trifluoromethyl)benzyl)(methyl)carbamoyl)-1-methyl-2-oxo-1,2-dihydroquinolin-4-yl)oxy)propyl)piperidine-1-carboxylate
150fold selectivity for isoform SGMS2 over SGMS1
1-methylcyclopropyl 4-(3-((3-((3-methoxy-5-(trifluoromethyl)benzyl)(methyl)carbamoyl)-1-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-4-yl)oxy)propyl)piperidine-1-carboxylate
inhibitor of isoform SGMS2 with good selectivity against SGMS1
2-(2-(benzyloxy)phenyl)-2-(phenylamino) acetonitrile
-
2-(4-(N-phenethylsulfamoyl)phenoxy)-N-(2-(trifluoromethoxy)phenyl)acetamide
-
2-(4-(N-phenethylsulfamoyl)phenoxy)-N-(o-tolyl)acetamide
-
2-(4-(N-phenethylsulfamoyl)phenoxy)-N-phenylacetamide
-
4-(2-((4-chlorobenzyl)amino)-2-oxoethoxy)-N-(pyridin-4-yl)benzamide
-
4-(2-((4-chlorobenzyl)amino)-2-oxoethoxy)-N-phenethylbenzamide
-
4-(3-((3-((3,5-bis(trifluoromethyl)benzyl)(methyl)carbamoyl)-1-methyl-2-oxo-1,2-dihydroquinolin-4-yl)oxy)propyl)piperidine-1-carboxylate
inhibitor of isoform SGMS2 with good selectivity against SGMS1
4-(3-(benzyloxy)pyrrolidin-1-yl)-N-(3,5-bis(trifluoromethyl)benzyl)-N,1-dimethyl-2-oxo-1,2-dihydroquinoline-3-carboxamide
inhibitor of isoform SGMS2 with good selectivity against SGMS1
lysenin
-
is a sphingomyelin-directed cytolysin purified from the earthworm, which specifically binds to membrane sphingomyelin and induces pore formation in the plasma membrane and subsequent cell death
-
N-(2-cyanophenyl)-2-(4-(N-phenethylsulfamoyl)phenoxy)acetamide
-
N-(2-methoxyphenyl)-2-(4-(N-phenethylsulfamoyl)phenoxy)acetamide
-
N-(2-nitrophenyl)-2-(4-(N-phenethylsulfamoyl)phenoxy)acetamide
-
N-(3,5-bis(trifluoromethyl)benzyl)-N,1-dimethyl-2-oxo-4-((2-phenylpyridin-4-yl)methoxy)-1,2-dihydroquinoline-3-carboxamide
880fold selectivity for isoform SGMS2 over SGMS1
N-(3,5-bis(trifluoromethyl)benzyl)-N,1-dimethyl-2-oxo-4-(4,4,4-trifluorobutoxy)-1,2-dihydroquinoline-3-carboxamide
inhibitor of isoform SGMS2 with good selectivity against SGMS1
N-(3,5-bis(trifluoromethyl)benzyl)-N,1-dimethyl-2-oxo-4-(pyrrolidin-1-yl)-1,2-dihydroquinoline-3-carboxamide
more than 100fold selectivity for isoform SGMS2 over SGMS1
N-(3-fluorobenzyl)-2-(4-(N-phenethylsulfamoyl)phenoxy)acetamide
-
N-(3-methoxyphenyl)-2-(4-(N-phenethylsulfamoyl)phenoxy)acetamide
-
N-(4-bromobenzyl)-2-(4-(N-phenethylsulfamoyl)phenoxy)acetamide
-
N-(4-chlorobenzyl)-2-(4-(N-(3-phenylpropyl)sulfamoyl)phenoxy)acetamide
-
N-(4-chlorobenzyl)-2-(4-(N-(4-chlorobenzyl)sulfamoyl)phenoxy)acetamide
-
N-(4-chlorobenzyl)-2-(4-(N-phenethylsulfamoyl)phenoxy)acetamide
-
N-(4-chlorobenzyl)-2-(4-(N-phenylsulfamoyl)phenoxy)acetamide
-
N-(4-chlorophenyl)-2-(4-(N-phenethylsulfamoyl)phenoxy)acetamide
-
N-(4-fluoro-2-methoxyphenyl)-2-(4-(N-phenethylsulfamoyl)phenoxy)acetamide
-
N-(4-fluorobenzyl)-2-(4-(N-phenethylsulfamoyl)phenoxy)acetamide
-
N-(4-fluorophenyl)-2-(4-(N-phenethylsulfamoyl)phenoxy)acetamide
-
N-(4-methoxybenzyl)-2-(4-(N-phenethylsulfamoyl)phenoxy)acetamide
-
N-(4-methoxyphenyl)-2-(4-(N-phenethylsulfamoyl)phenoxy)acetamide
-
N-benzyl-2-(4-(N-phenethylsulfamoyl)phenoxy)acetamide
-
N-phenethyl-2-(4-(N-phenethylsulfamoyl)phenoxy)acetamide
-
potassium tricyclodecan-9-yl-xanthogenate
-
i.e. D609, decreases enzyme activity an sphingomyelin levels in different human cell lines in vivo
tert-butyl 4-(3-((3-((3,5-dimethoxybenzyl)(methyl)carbamoyl)-1-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-4-yl)oxy)propyl)piperidine-1-carboxylate
inhibitor of isoform SGMS2 with good selectivity against SGMS1
tert-butyl 4-(3-((3-((3,5-dimethoxybenzyl)(methyl)carbamoyl)-1-methyl-2-oxo-1,2-dihydroquinolin-4-yl)oxy)propyl)piperidine-1-carboxylate
inhibitor of isoform SGMS2 with good selectivity against SGMS1
tricyclodecan-9-yl-xanthogenate
-
tricyclodecane-9-yl xanthogenate
i.e. D609
-
tumor necrosis factor-alpha
-
-
-
D609
-
-
D609
-
complete in inhibition at 0.35 mM
tricyclodecan-9-yl-xanthogenate
-
-
tricyclodecan-9-yl-xanthogenate
-
i.e. D609
-
tricyclodecan-9-yl-xanthogenate
i.e. D609
-
tricyclodecan-9-yl-xanthogenate
i.e. D609
-
tricyclodecan-9-yl-xanthogenate
-
sphingomyelin synthase is a potential target for tricyclodecan-9-yl-xanthogenate (D609) and inhibition of sphingomyelin synthase may contribute to D609-induced cell death via modulation of the cellular levels of ceramide and diacylglycerol
-
additional information
design of dual inhibitors of secretory phospholipase A2 and sphingomyelin synthase by linking or fusing sphingomyelin synthase inhibitor fragment Ly18 (N-pyridine-3-amide moiety) with phospholipase A2 inhibitor fragment (indole-3-acetamide structure) by 3-6 carbon chain
-
additional information
-
photosensitizer Pc 4, PDT, induces inhibition of SMS in Jurkat cells
-
additional information
structure-based virtual screening, synthesis and biological evaluation of 2-(4-(N-phenethylsulfamoyl)phenoxy)acetamides (SAPAs) as sphingomyelin synthase 1 inhibitors, molecular docking studies and interaction modes of SMS1 inhibitors with the active site of SMS1, overview
-
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Acquired Immunodeficiency Syndrome
Current status and perspectives in ceramide-targeting molecular medicine.
Alzheimer Disease
Current status and perspectives in ceramide-targeting molecular medicine.
Alzheimer Disease
Inhibition of sphingomyelin synthase 1 ameliorates alzheimer-like pathology in APP/PS1 transgenic mice through promoting lysosomal degradation of BACE1.
Asthma
Ceramide/sphingosine-1-phosphate imbalance is associated with distinct inflammatory phenotypes of uncontrolled asthma.
Atherosclerosis
Current status and perspectives in ceramide-targeting molecular medicine.
Atherosclerosis
Discovery of 4-Benzyloxybenzo[ d]isoxazole-3-amine Derivatives as Highly Selective and Orally Efficacious Human Sphingomyelin Synthase 2 Inhibitors that Reduce Chronic Inflammation in db/ db Mice.
Atherosclerosis
Discovery of the selective sphingomyelin synthase 2 inhibitors with the novel structure of oxazolopyridine.
Atherosclerosis
Discovery, synthesis and anti-atherosclerotic activities of a novel selective sphingomyelin synthase 2 inhibitor.
Atherosclerosis
Discovery, synthesis and biological evaluation of 2-(4-(N-phenethylsulfamoyl)phenoxy)acetamides (SAPAs) as novel sphingomyelin synthase 1 inhibitors.
Atherosclerosis
Impact of sphingomyelin synthase 1 deficiency on sphingolipid metabolism and atherosclerosis in mice.
Atherosclerosis
Macrophage sphingomyelin synthase 2 deficiency decreases atherosclerosis in mice.
Atherosclerosis
Pharmacologic inhibition of sphingomyelin synthase (SMS) activity reduces apolipoprotein-B secretion from hepatocytes and attenuates endotoxin-mediated macrophage inflammation.
Atherosclerosis
Pharmacological Activation of Peroxisome Proliferator-Activated Receptor {Delta} Increases Sphingomyelin Synthase Activity in THP-1 Macrophage-Derived Foam Cell.
Atherosclerosis
Sphingomyelin synthase 1 enhances BCR signaling to promote lupus-like autoimmune response.
Atherosclerosis
Sphingomyelin synthase 2 over-expression induces expression of aortic inflammatory biomarkers and decreases circulating EPCs in ApoE KO mice.
Atherosclerosis
[Sphingomyelin synthase 2 deficiency decreases atherosclerosis and inhibits inflammation in mice.]
Bacterial Infections
Current status and perspectives in ceramide-targeting molecular medicine.
Brain Ischemia
Expression of sphingomyelin synthase 1 gene in rat brain focal ischemia.
Breast Neoplasms
Sphingomyelin synthase 2 promotes an aggressive breast cancer phenotype by disrupting the homoeostasis of ceramide and sphingomyelin.
Carcinogenesis
Overriding sorafenib resistance via blocking lipid metabolism and Ras by sphingomyelin synthase 1 inhibition in hepatocellular carcinoma.
Carcinoma
LncRNA THAP9-AS1 accelerates cell growth of esophageal squamous cell carcinoma through sponging miR-335-5p to regulate SGMS2.
Carcinoma, Hepatocellular
Overriding sorafenib resistance via blocking lipid metabolism and Ras by sphingomyelin synthase 1 inhibition in hepatocellular carcinoma.
Cardiomyopathies
HILIC-MS-based metabolomics reveal that Astragalus polysaccharide alleviates doxorubicin-induced cardiomyopathy by regulating sphingolipid and glycerophospholipid homeostasis.
Colitis-Associated Neoplasms
Sphingomyelin synthase 2 deficiency inhibits the induction of murine colitis-associated colon cancer.
Coronary Disease
[Sphingomyelin synthase 2 deficiency decreases atherosclerosis and inhibits inflammation in mice.]
Dermatitis, Atopic
Current status and perspectives in ceramide-targeting molecular medicine.
Diabetes Mellitus
Current status and perspectives in ceramide-targeting molecular medicine.
Diabetes Mellitus
Deficiency of sphingomyelin synthase 2 prolongs survival by the inhibition of lymphoma infiltration through ICAM-1 reduction.
Diabetes Mellitus, Type 2
Lipid environment induces ER stress, TXNIP expression and inflammation in immune cells of individuals with type 2 diabetes.
Encephalitis, Japanese
Sphingomyelin generated by sphingomyelin synthase 1 is involved in attachment and infection with Japanese encephalitis virus.
Esophageal Squamous Cell Carcinoma
LncRNA THAP9-AS1 accelerates cell growth of esophageal squamous cell carcinoma through sponging miR-335-5p to regulate SGMS2.
Fatty Liver
Discovery of 4-Benzyloxybenzo[ d]isoxazole-3-amine Derivatives as Highly Selective and Orally Efficacious Human Sphingomyelin Synthase 2 Inhibitors that Reduce Chronic Inflammation in db/ db Mice.
Fatty Liver
Imaging Mass Spectrometry Reveals Acyl-Chain- and Region-Specific Sphingolipid Metabolism in the Kidneys of Sphingomyelin Synthase 2-Deficient Mice.
Fatty Liver
Sphingolipids in lipid microdomains and obesity.
Fatty Liver
Sphingomyelin synthase 1 mediates hepatocyte pyroptosis to trigger non-alcoholic steatohepatitis.
Fatty Liver
Sphingomyelin synthase 2 activity and liver steatosis: an effect of ceramide-mediated peroxisome proliferator-activated receptor ?2 suppression.
Glioma
Sphingomyelin and sphingomyelin synthase (SMS) in the malignant transformation of glioma cells and in 2-hydroxyoleic acid therapy.
Glucose Intolerance
Sphingolipids in lipid microdomains and obesity.
Hepatitis
CD4+ T-cell dysfunctions through the impaired lipid rafts ameliorate concanavalin A-induced hepatitis in sphingomyelin synthase 1-knockout mice.
Hepatitis
Sphingomyelin synthase 1 enhances BCR signaling to promote lupus-like autoimmune response.
Infarction, Middle Cerebral Artery
Protection by D609 Through Cell-Cycle Regulation After Stroke.
Infections
A Genome-Wide CRISPR/Cas9 Screen Reveals the Requirement of Host Sphingomyelin Synthase 1 for Infection with Pseudorabies Virus Mutant gD-Pass.
Infections
Sphingomyelin generated by sphingomyelin synthase 1 is involved in attachment and infection with Japanese encephalitis virus.
Insulin Resistance
A selective sphingomyelin synthase 2 inhibitor ameliorates diet induced insulin resistance via the IRS-1/Akt/GSK-3? signaling pathway.
Insulin Resistance
Characterization of the role of sphingomyelin synthase 2 in glucose metabolism in whole-body and peripheral tissues in mice.
Insulin Resistance
Discovery of 4-Benzyloxybenzo[ d]isoxazole-3-amine Derivatives as Highly Selective and Orally Efficacious Human Sphingomyelin Synthase 2 Inhibitors that Reduce Chronic Inflammation in db/ db Mice.
Insulin Resistance
Dynamic modification of sphingomyelin in lipid microdomains controls development of obesity, Fatty liver, and type 2 diabetes.
Insulin Resistance
GPRC5B-Mediated Sphingomyelin Synthase 2 Phosphorylation Plays a Critical Role in Insulin Resistance.
Leukemia
Ceramide generation during curcumin-induced apoptosis is controlled by crosstalk among Bcl-2, Bcl-xL, caspases and glutathione.
Leukemia
Current status and perspectives in ceramide-targeting molecular medicine.
Leukemia
MiR-130b and miR-128a are essential lineage-specific co-drivers of t(4;11) MLL-AF4 acute leukemia.
Leukemia
Possible role of ceramide as an indicator of chemoresistance: decrease of the ceramide content via activation of glucosylceramide synthase and sphingomyelin synthase in chemoresistant leukemia.
Leukemia
Prodrug modification increases potassium tricyclo[5.2.1.0(2,6)]-decan-8-yl dithiocarbonate (D609) chemical stability and cytotoxicity against U937 leukemia cells.
Leukemia
Sphingomyelin synthase as a potential target for D609-induced apoptosis in U937 human monocytic leukemia cells.
Leukemia, Myelogenous, Chronic, BCR-ABL Positive
Bcr-Abl regulation of sphingomyelin synthase 1 reveals a novel oncogenic-driven mechanism of protein up-regulation.
Liver Diseases
Imaging Mass Spectrometry Reveals Acyl-Chain- and Region-Specific Sphingolipid Metabolism in the Kidneys of Sphingomyelin Synthase 2-Deficient Mice.
Lung Injury
Sphingomyelin synthase 2 (SMS2) deficiency attenuates LPS-induced lung injury.
Lymphoma
Deficiency of sphingomyelin synthase 2 prolongs survival by the inhibition of lymphoma infiltration through ICAM-1 reduction.
Lymphoma
Phosphoinositide phosphatase SHIP-1 regulates apoptosis induced by edelfosine, Fas ligation and DNA damage in mouse lymphoma cells.
Magnesium Deficiency
Short-term magnesium deficiency upregulates sphingomyelin synthase and p53 in cardiovascular tissues and cells : relevance to de novo synthesis of ceramide.
Malaria
Neutral sphingomyelinase activity dependent on Mg2+ and anionic phospholipids in the intraerythrocytic malaria parasite Plasmodium falciparum.
Malaria
Plasmodium falciparum exports the Golgi marker sphingomyelin synthase into a tubovesicular network in the cytoplasm of mature erythrocytes.
Malaria
Sphingolipid synthesis as a target for chemotherapy against malaria parasites.
Melanoma
Nuclear sphingomyelin-synthase and protein kinase C delta in melanoma cells.
Melanoma
Sphingomyelin Synthase 1 (SMS1) Downregulation Is Associated With Sphingolipid Reprogramming and a Worse Prognosis in Melanoma.
Metabolic Diseases
Discovery of 1,8-naphthyridin-2-one derivative as a potent and selective sphingomyelin synthase 2 inhibitor.
Neoplasm Metastasis
Sphingomyelin synthase 2 promotes an aggressive breast cancer phenotype by disrupting the homoeostasis of ceramide and sphingomyelin.
Neoplasms
Alteration of Ceramide 1-O-Functionalization as a Promising Approach for Cancer Therapy.
Neoplasms
Current status and perspectives in ceramide-targeting molecular medicine.
Neoplasms
Discovery of 4-Benzyloxybenzo[ d]isoxazole-3-amine Derivatives as Highly Selective and Orally Efficacious Human Sphingomyelin Synthase 2 Inhibitors that Reduce Chronic Inflammation in db/ db Mice.
Neoplasms
Identification and functional analysis of the risk microRNAs associated with cerebral low-grade glioma prognosis.
Neoplasms
LC-HRMS based approach to identify novel sphingolipid biomarkers in breast cancer patients.
Neoplasms
Measurement of ceramide and sphingolipid metabolism in tumors: potential modulation of chemotherapy.
Neoplasms
Method to Measure Sphingomyelin Synthase Activity Changes in Response to CD95L.
Neoplasms
MiR-130b and miR-128a are essential lineage-specific co-drivers of t(4;11) MLL-AF4 acute leukemia.
Neoplasms
MS-209 Schering.
Neoplasms
Normalization of sphingomyelin levels by 2-hydroxyoleic acid induces autophagic cell death of SF767 cancer cells.
Neoplasms
Sphingomyelin synthase 2 but not sphingomyelin synthase 1 is upregulated in ovarian cancer and involved in migration, growth and survival via different mechanisms.
Neoplasms
Sphingomyelin synthase 2 facilitates M2-like macrophage polarization and tumor progression in a mouse model of triple-negative breast cancer.
Neoplasms
Sphingomyelin synthase 2 promotes an aggressive breast cancer phenotype by disrupting the homoeostasis of ceramide and sphingomyelin.
Neoplasms
Sphingomyelin synthase as a potential target for D609-induced apoptosis in U937 human monocytic leukemia cells.
Neoplasms
The role of sphingomyelin and sphingomyelin synthases in cell death, proliferation and migration-from cell and animal models to human disorders.
Neoplasms
The sustained activation of sphingomyelin synthase by 2-hydroxyoleic acid induces sphingolipidosis in tumor cells.
Neoplasms
[Expression of sphingomyelin synthase 1 (SGMS1) gene varies in human lung and oesophagus cancer].
Obesity
Characterization of the role of sphingomyelin synthase 2 in glucose metabolism in whole-body and peripheral tissues in mice.
Obesity
Deficiency of sphingomyelin synthase 2 prolongs survival by the inhibition of lymphoma infiltration through ICAM-1 reduction.
Obesity
Dynamic modification of sphingomyelin in lipid microdomains controls development of obesity, Fatty liver, and type 2 diabetes.
Obesity
Malabaricone C as Natural Sphingomyelin Synthase Inhibitor against Diet-Induced Obesity and Its Lipid Metabolism in Mice.
Obesity
Sphingomyelin synthase 2 loss suppresses steatosis but exacerbates fibrosis in the liver of mice fed with choline-deficient, L-amino acid-defined, high-fat diet.
Osteoporosis
A Novel IFITM5 Variant Associated with Phenotype of Osteoporosis with Calvarial Doughnut Lesions: A Case Report.
Osteoporosis
Early-Onset Osteoporosis.
Osteoporosis
Musculoskeletal phenotype in two unrelated individuals with a recurrent nonsense variant in SGMS2.
Osteoporosis
Osteoporosis and skeletal dysplasia caused by pathogenic variants in SGMS2.
Ovarian Neoplasms
Sphingomyelin synthase 2 but not sphingomyelin synthase 1 is upregulated in ovarian cancer and involved in migration, growth and survival via different mechanisms.
Pseudorabies
A Genome-Wide CRISPR/Cas9 Screen Reveals the Requirement of Host Sphingomyelin Synthase 1 for Infection with Pseudorabies Virus Mutant gD-Pass.
Pulmonary Disease, Chronic Obstructive
Airway Resistance Caused by Sphingomyelin Synthase 2 Insufficiency in Response to Cigarette Smoke.
Reperfusion Injury
Sphingomyelin Synthase 2 Inhibition Ameliorates Cerebral Ischemic Reperfusion Injury Through Reducing the Recruitment of Toll-Like Receptor 4 to Lipid Rafts.
Sarcoma
Quantifying Fluorescently Labeled Ceramide Levels in Human Sarcoma Cell Lines in Response to a Sphingomyelin Synthase Inhibitor.
Sphingolipidoses
The sustained activation of sphingomyelin synthase by 2-hydroxyoleic acid induces sphingolipidosis in tumor cells.
sphingomyelin synthase deficiency
A novel mechanism of thrombocytopenia by PS exposure through TMEM16F in sphingomyelin synthase 1 deficiency.
sphingomyelin synthase deficiency
Effect of liver total sphingomyelin synthase deficiency on plasma lipid metabolism.
sphingomyelin synthase deficiency
Impact of sphingomyelin synthase 1 deficiency on sphingolipid metabolism and atherosclerosis in mice.
sphingomyelin synthase deficiency
Macrophage sphingomyelin synthase 2 deficiency decreases atherosclerosis in mice.
sphingomyelin synthase deficiency
Sphingomyelin synthase 2 deficiency attenuates NFkappaB activation.
sphingomyelin synthase deficiency
Sphingomyelin synthase 2 deficiency inhibits the induction of murine colitis-associated colon cancer.
sphingomyelin synthase deficiency
[Sphingomyelin synthase 2 deficiency decreases atherosclerosis and inhibits inflammation in mice.]
Thrombocytopenia
A novel mechanism of thrombocytopenia by PS exposure through TMEM16F in sphingomyelin synthase 1 deficiency.
Triple Negative Breast Neoplasms
Sphingomyelin synthase 2 facilitates M2-like macrophage polarization and tumor progression in a mouse model of triple-negative breast cancer.
Virus Diseases
Enzyme distributions in subcellular fractions of BHK cells infected with Semliki forest virus: evidence for a major fraction of sphingomyelin synthase in the trans-golgi network.
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0.000047
1-methylcyclopropyl 4-(3-((3-((3,5-bis(trifluoromethyl)benzyl)(methyl)carbamoyl)-1-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-4-yl)oxy)propyl)piperidine-1-carboxylate
Homo sapiens
pH 7.5, 23°C
0.0000065
1-methylcyclopropyl 4-(3-((3-((3,5-bis(trifluoromethyl)benzyl)(methyl)carbamoyl)-1-methyl-2-oxo-1,2-dihydroquinolin-4-yl)oxy)propyl)piperidine-1-carboxylate
Homo sapiens
pH 7.5, 23°C
0.000045
1-methylcyclopropyl 4-(3-((3-((3-methoxy-5-(trifluoromethyl)benzyl)(methyl)carbamoyl)-1-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-4-yl)oxy)propyl)piperidine-1-carboxylate
Homo sapiens
pH 7.5, 23°C
0.00099
2-((2,5-dichlorobenzyl)oxy)-N-(pyridin-3-yl)benzamide
Homo sapiens
pH 7.4, 37°C
0.0028
2-((2,5-dimethoxybenzyl)oxy)-N-(pyridin-3-yl)benzamide
Homo sapiens
pH 7.4, 37°C
0.00069
2-((2,6-dichlorobenzyl)oxy)-N-(pyridin-3-yl)benzamide
Homo sapiens
pH 7.4, 37°C
0.00089
2-((2,6-dimethylbenzyl)oxy)-N-(pyridin-3-yl)benzamide
Homo sapiens
pH 7.4, 37°C
0.00067
2-((2-((5-chloropentyl)oxy)benzyl)oxy)-N-(pyridin-3-yl)benzamide
Homo sapiens
pH 7.4, 37°C
0.00047
2-((2-((6-chlorohexyl)oxy)benzyl)oxy)-N-(pyridin-3-yl)benzamide
Homo sapiens
pH 7.4, 37°C
0.0013
2-((2-(4-chlorobutoxy)benzyl)oxy)-N-(pyridin-3-yl)benzamide
Homo sapiens
pH 7.4, 37°C
0.00074
2-((2-chloro-5-fluorobenzyl)oxy)-N-(pyridin-3-yl)benzamide
Homo sapiens
pH 7.4, 37°C
0.0015
2-((2-chloro-6-fluorobenzyl)oxy)-N-(pyridin-3-yl)benzamide
Homo sapiens
pH 7.4, 37°C
0.0011
2-((2-chlorobenzyl)oxy)-N-(pyridin-3-yl)benzamide
Homo sapiens
pH 7.4, 37°C
0.00088
2-((2-ethylbenzyl)oxy)-N-(pyridin-3-yl)benzamide
Homo sapiens
pH 7.4, 37°C
0.0035
2-((2-fluorobenzyl)oxy)-N-(pyridin-3-yl)benzamide
Homo sapiens
pH 7.4, 37°C
0.0015
2-((2-methylbenzyl)oxy)-N-(pyridin-3-yl)benzamide
Homo sapiens
pH 7.4, 37°C
0.0031
2-((3-chloro-2-fluorobenzyl)oxy)-N-(pyridin-3-yl)benzamide
Homo sapiens
pH 7.4, 37°C
0.0038
2-((3-chloro-2-methylbenzyl)oxy)-N-(pyridin-3-yl)benzamide
Homo sapiens
pH 7.4, 37°C
0.0014
2-((3-chlorobenzyl)oxy)-N-(pyridin-3-yl)benzamide
Homo sapiens
pH 7.4, 37°C
0.0016
2-((3-fluorobenzyl)oxy)-N-(pyridin-3-yl)benzamide
Homo sapiens
pH 7.4, 37°C
0.0116
2-((5-chloro-2-(2-methoxyethoxy)benzyl)oxy)-N-(pyridin-3-yl)benzamide
Homo sapiens
pH 7.4, 37°C
0.0041
2-((5-chloro-2-(3-methoxypropoxy)benzyl)oxy)-N-(pyridin-3-yl)benzamide
Homo sapiens
pH 7.4, 37°C
0.00043
2-((5-chloro-2-(heptyloxy)benzyl)oxy)-N-(pyridin-3-yl)benzamide
Homo sapiens
pH 7.4, 37°C
0.00052
2-((5-chloro-2-(hexyloxy)benzyl)oxy)-N-(pyridin-3-yl)benzamide
Homo sapiens
pH 7.4, 37°C
0.00067
2-((5-chloro-2-methoxybenzyl)oxy)-N-(pyridin-3-yl)benzamide
Homo sapiens
pH 7.4, 37°C
0.0011
2-((5-chloro-2-methylbenzyl)oxy)-N-(pyridin-3-yl)benzamide
Homo sapiens
pH 7.4, 37°C
0.00074
2-((5-fluoro-2-methylbenzyl)oxy)-N-(pyridin-3-yl)benzamide
Homo sapiens
pH 7.4, 37°C
0.0117
2-(benzyloxy)-N-(pyridin-2-yl)benzamide
Homo sapiens
pH 7.4, 37°C
0.0032
2-(benzyloxy)-N-(pyridin-3-yl)benzamide
Homo sapiens
pH 7.4, 37°C
0.0017
2-[2-[(2-methylphenyl)methoxy]phenyl][1,3]oxazolo[5,4-b]pyridine
Homo sapiens
pH 7.4, 37°C
0.0253
2-[[2-((5-(3-(2-amino-2-oxoethyl)-5-methoxy-2-methyl-1H-indol-1-yl)pentyl)oxy)benzyl]oxy]-N-(pyridin-3-yl)benzamide
Homo sapiens
pH 7.4, 37°C
0.0287
2-[[2-((6-(3-(2-amino-2-oxoethyl)-5-methoxy-2-methyl-1H-indol-1-yl)hexyl)oxy)benzyl]oxy]-N-(pyridin-3-yl)benzamide
Homo sapiens
pH 7.4, 37°C
0.0265
2-[[2-(3-(3-(2-amino-2-oxoethyl)-5-methoxy-2-methyl-1H-indol-1-yl)propoxy)benzyl]oxy]-N-(pyridin-3-yl)benzamide
Homo sapiens
pH 7.4, 37°C
0.0617
2-[[2-(4-(3-(2-amino-2-oxoethyl)-5-methoxy-2-methyl-1H-indol-1-yl)butoxy)benzyl]oxy]-N-(pyridin-3-yl)benzamide
Homo sapiens
pH 7.4, 37°C
0.00003
4-(3-((3-((3,5-bis(trifluoromethyl)benzyl)(methyl)carbamoyl)-1-methyl-2-oxo-1,2-dihydroquinolin-4-yl)oxy)propyl)piperidine-1-carboxylate
Homo sapiens
pH 7.5, 23°C
0.00061
4-(3-(benzyloxy)pyrrolidin-1-yl)-N-(3,5-bis(trifluoromethyl)benzyl)-N,1-dimethyl-2-oxo-1,2-dihydroquinoline-3-carboxamide
Homo sapiens
pH 7.5, 23°C
1.065
D609
Homo sapiens
isoform SMS2, in 50 mM TrisHCl (pH 7.4), at 22°C
0.000016
N-(3,5-bis(trifluoromethyl)benzyl)-N,1-dimethyl-2-oxo-4-((2-phenylpyridin-4-yl)methoxy)-1,2-dihydroquinoline-3-carboxamide
Homo sapiens
pH 7.5, 23°C
0.00012
N-(3,5-bis(trifluoromethyl)benzyl)-N,1-dimethyl-2-oxo-4-(4,4,4-trifluorobutoxy)-1,2-dihydroquinoline-3-carboxamide
Homo sapiens
pH 7.5, 23°C
0.00095
N-(3,5-bis(trifluoromethyl)benzyl)-N,1-dimethyl-2-oxo-4-(pyrrolidin-1-yl)-1,2-dihydroquinoline-3-carboxamide
Homo sapiens
pH 7.5, 23°C
0.0021
N-(pyridin-3-yl)-2-((2-(trifluoromethyl)benzyl)oxy)benzamide
Homo sapiens
pH 7.4, 37°C
0.0021
N-[(4-bromophenyl)methyl]-2-[4-[(2-phenylethyl)sulfamoyl]phenoxy]acetamide
Homo sapiens
pH 7.4, 37°C
0.00013
tert-butyl 4-(3-((3-((3,5-dimethoxybenzyl)(methyl)carbamoyl)-1-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-4-yl)oxy)propyl)piperidine-1-carboxylate
Homo sapiens
pH 7.5, 23°C
0.000091
tert-butyl 4-(3-((3-((3,5-dimethoxybenzyl)(methyl)carbamoyl)-1-methyl-2-oxo-1,2-dihydroquinolin-4-yl)oxy)propyl)piperidine-1-carboxylate
Homo sapiens
pH 7.5, 23°C
0.056
tricyclodecane-9-yl xanthogenate
Homo sapiens
pH 7.5, 23°C
-
0.00085
1-methylcyclopropyl 4-(3-((3-((3,5-bis(trifluoromethyl)benzyl)(methyl)carbamoyl)-1-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-4-yl)oxy)propyl)piperidine-1-carboxylate
Homo sapiens
pH 7.5, 23°C
0.001
1-methylcyclopropyl 4-(3-((3-((3,5-bis(trifluoromethyl)benzyl)(methyl)carbamoyl)-1-methyl-2-oxo-1,2-dihydroquinolin-4-yl)oxy)propyl)piperidine-1-carboxylate
Homo sapiens
pH 7.5, 23°C
0.0024
1-methylcyclopropyl 4-(3-((3-((3-methoxy-5-(trifluoromethyl)benzyl)(methyl)carbamoyl)-1-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-4-yl)oxy)propyl)piperidine-1-carboxylate
Homo sapiens
pH 7.5, 23°C
0.025
2-(2-(benzyloxy)phenyl)-2-(phenylamino) acetonitrile
Homo sapiens
pH 7.4, 37°C
0.1
2-(4-(N-phenethylsulfamoyl)phenoxy)-N-(2-(trifluoromethoxy)phenyl)acetamide
Homo sapiens
pH 7.4, 37°C
0.1
2-(4-(N-phenethylsulfamoyl)phenoxy)-N-(o-tolyl)acetamide
Homo sapiens
pH 7.4, 37°C
0.0147
2-(4-(N-phenethylsulfamoyl)phenoxy)-N-phenylacetamide
Homo sapiens
pH 7.4, 37°C
0.1
4-(2-((4-chlorobenzyl)amino)-2-oxoethoxy)-N-(pyridin-4-yl)benzamide
Homo sapiens
pH 7.4, 37°C
0.1
4-(2-((4-chlorobenzyl)amino)-2-oxoethoxy)-N-phenethylbenzamide
Homo sapiens
pH 7.4, 37°C
0.0034
4-(3-((3-((3,5-bis(trifluoromethyl)benzyl)(methyl)carbamoyl)-1-methyl-2-oxo-1,2-dihydroquinolin-4-yl)oxy)propyl)piperidine-1-carboxylate
Homo sapiens
pH 7.5, 23°C
0.015
4-(3-(benzyloxy)pyrrolidin-1-yl)-N-(3,5-bis(trifluoromethyl)benzyl)-N,1-dimethyl-2-oxo-1,2-dihydroquinoline-3-carboxamide
Homo sapiens
pH 7.5, 23°C
0.622
D609
Homo sapiens
isoform SMS1, in 50 mM TrisHCl (pH 7.4), at 22°C
0.1
N-(2-cyanophenyl)-2-(4-(N-phenethylsulfamoyl)phenoxy)acetamide
Homo sapiens
pH 7.4, 37°C
0.0142
N-(2-methoxyphenyl)-2-(4-(N-phenethylsulfamoyl)phenoxy)acetamide
Homo sapiens
pH 7.4, 37°C
0.1
N-(2-nitrophenyl)-2-(4-(N-phenethylsulfamoyl)phenoxy)acetamide
Homo sapiens
pH 7.4, 37°C
0.014
N-(3,5-bis(trifluoromethyl)benzyl)-N,1-dimethyl-2-oxo-4-((2-phenylpyridin-4-yl)methoxy)-1,2-dihydroquinoline-3-carboxamide
Homo sapiens
pH 7.5, 23°C
0.025
N-(3,5-bis(trifluoromethyl)benzyl)-N,1-dimethyl-2-oxo-4-(4,4,4-trifluorobutoxy)-1,2-dihydroquinoline-3-carboxamide
Homo sapiens
pH 7.5, 23°C
0.0156
N-(3-fluorobenzyl)-2-(4-(N-phenethylsulfamoyl)phenoxy)acetamide
Homo sapiens
pH 7.4, 37°C
0.0092
N-(3-methoxyphenyl)-2-(4-(N-phenethylsulfamoyl)phenoxy)acetamide
Homo sapiens
pH 7.4, 37°C
0.0021
N-(4-bromobenzyl)-2-(4-(N-phenethylsulfamoyl)phenoxy)acetamide
Homo sapiens
pH 7.4, 37°C
0.1
N-(4-chlorobenzyl)-2-(4-(N-(3-phenylpropyl)sulfamoyl)phenoxy)acetamide
Homo sapiens
pH 7.4, 37°C
0.05
N-(4-chlorobenzyl)-2-(4-(N-(4-chlorobenzyl)sulfamoyl)phenoxy)acetamide
Homo sapiens
pH 7.4, 37°C
0.0052
N-(4-chlorobenzyl)-2-(4-(N-phenethylsulfamoyl)phenoxy)acetamide
Homo sapiens
pH 7.4, 37°C
0.1
N-(4-chlorobenzyl)-2-(4-(N-phenylsulfamoyl)phenoxy)acetamide
Homo sapiens
pH 7.4, 37°C
0.0066
N-(4-chlorophenyl)-2-(4-(N-phenethylsulfamoyl)phenoxy)acetamide
Homo sapiens
pH 7.4, 37°C
0.1
N-(4-fluoro-2-methoxyphenyl)-2-(4-(N-phenethylsulfamoyl)phenoxy)acetamide
Homo sapiens
pH 7.4, 37°C
0.0081
N-(4-fluorobenzyl)-2-(4-(N-phenethylsulfamoyl)phenoxy)acetamide
Homo sapiens
pH 7.4, 37°C
0.0105
N-(4-fluorophenyl)-2-(4-(N-phenethylsulfamoyl)phenoxy)acetamide
Homo sapiens
pH 7.4, 37°C
0.0059
N-(4-methoxybenzyl)-2-(4-(N-phenethylsulfamoyl)phenoxy)acetamide
Homo sapiens
pH 7.4, 37°C
0.05
N-(4-methoxyphenyl)-2-(4-(N-phenethylsulfamoyl)phenoxy)acetamide
Homo sapiens
pH 7.4, 37°C
0.0231
N-benzyl-2-(4-(N-phenethylsulfamoyl)phenoxy)acetamide
Homo sapiens
pH 7.4, 37°C
0.05
N-phenethyl-2-(4-(N-phenethylsulfamoyl)phenoxy)acetamide
Homo sapiens
pH 7.4, 37°C
0.01
tert-butyl 4-(3-((3-((3,5-dimethoxybenzyl)(methyl)carbamoyl)-1-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-4-yl)oxy)propyl)piperidine-1-carboxylate
Homo sapiens
pH 7.5, 23°C
0.019
tert-butyl 4-(3-((3-((3,5-dimethoxybenzyl)(methyl)carbamoyl)-1-methyl-2-oxo-1,2-dihydroquinolin-4-yl)oxy)propyl)piperidine-1-carboxylate
Homo sapiens
pH 7.5, 23°C
0.219
tricyclodecan-9-yl-xanthogenate
Homo sapiens
pH 7.4, 37°C
-
0.056
tricyclodecane-9-yl xanthogenate
Homo sapiens
pH 7.5, 23°C
-
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Vivekananda, J.; Smith, D.; King, R.J.
Sphingomyelin metabolites inhibit sphingomyelin synthase and CTP:phosphocholine cytidylyltransferase
Am. J. Physiol.
281
L98-L107
2001
Homo sapiens
brenda
Albi, E.; La Porta, C.A.; Cataldi, S.; Magni, M.V.
Nuclear sphingomyelin-synthase and protein kinase C delta in melanoma cells
Arch. Biochem. Biophys.
438
156-161
2005
Homo sapiens, Mus musculus
brenda
Huitema, K.; van den Dikkenberg, J.; Brouwers, J.F.H.M.; Holthuis, J.C.M.
Identification of a family of animal sphingomyelin synthases
EMBO J.
23
33-44
2004
Caenorhabditis elegans (Q20735), Caenorhabditis elegans (Q9U3D4), Caenorhabditis elegans, Homo sapiens (Q86VZ5), Homo sapiens (Q8NHU3), Homo sapiens, Mus musculus (Q8VCQ6), Mus musculus
brenda
Meng, A.; Luberto, C.; Meier, P.; Bai, A.; Yang, X.; Hannun, Y.A.; Zhou, D.
Sphingomyelin synthase as a potential target for D609-induced apoptosis in U937 human monocytic leukemia cells
Exp. Cell Res.
292
385-392
2004
Homo sapiens
brenda
Luberto, C.; Hannun, Y.A.
Sphingomyelin synthase, a potential regulator of intracellular levels of ceramide and diacylglycerol during SV40 transformation. Does sphingomyelin synthase account for the putative phosphatidylcholine-specific phospholipase C?
J. Biol. Chem.
273
14550-14559
1998
Homo sapiens
brenda
Yamaoka, S.; Miyaji, M.; Kitano, T.; Umehara, H.; Okazaki, T.
Expression cloning of a human cDNA restoring sphingomyelin synthesis and cell growth in sphingomyelin synthase-defective lymphoid cells
J. Biol. Chem.
279
18688-18693
2004
Homo sapiens (Q86VZ5), Homo sapiens
brenda
Tafesse, F.G.; Ternes, P.; Holthuis, J.C.
The multigenic sphingomyelin synthase family
J. Biol. Chem.
281
29421-29425
2006
Mus musculus, Pseudomonas aeruginosa, Homo sapiens (Q86VZ5), Homo sapiens (Q8NHU3)
brenda
Hailemariam, T.K.; Huan, C.; Liu, J.; Li, Z.; Roman, C.; Kalbfeisch, M.; Bui, H.H.; Peake, D.A.; Kuo, M.; Cao, G.; Wadgaonkar, R.; Jiang, X.
Sphingomyelin synthase 2 deficiency attenuates NFkappaB activation
Arterioscler. Thromb. Vasc. Biol.
28
1519-1526
2008
Homo sapiens, Mus musculus
brenda
Separovic, D.; Hanada, K.; Maitah, M.Y.; Nagy, B.; Hang, I.; Tainsky, M.A.; Kraniak, J.M.; Bielawski, J.
Sphingomyelin synthase 1 suppresses ceramide production and apoptosis post-photodamage
Biochem. Biophys. Res. Commun.
358
196-202
2007
Homo sapiens
brenda
Villani, M.; Subathra, M.; Im, Y.B.; Choi, Y.; Signorelli, P.; Del Poeta, M.; Luberto, C.
Sphingomyelin synthases regulate production of diacylglycerol at the Golgi
Biochem. J.
414
31-41
2008
Homo sapiens
brenda
Li, Z.; Hailemariam, T.K.; Zhou, H.; Li, Y.; Duckworth, D.C.; Peake, D.A.; Zhang, Y.; Kuo, M.S.; Cao, G.; Jiang, X.C.
Inhibition of sphingomyelin synthase (SMS) affects intracellular sphingomyelin accumulation and plasma membrane lipid organization
Biochim. Biophys. Acta
1771
1186-1194
2007
Homo sapiens
brenda
Yeang, C.; Varshney, S.; Wang, R.; Zhang, Y.; Ye, D.; Jiang, X.C.
The domain responsible for sphingomyelin synthase (SMS) activity
Biochim. Biophys. Acta
1781
610-617
2008
Homo sapiens (Q86VZ5), Homo sapiens (Q8NHU3)
brenda
Separovic, D.; Semaan, L.; Tarca, A.L.; Awad Maitah, M.Y.; Hanada, K.; Bielawski, J.; Villani, M.; Luberto, C.
Suppression of sphingomyelin synthase 1 by small interference RNA is associated with enhanced ceramide production and apoptosis after photodamage
Exp. Cell Res.
314
1860-1868
2008
Homo sapiens
brenda
Jin, Z.X.; Huang, C.R.; Dong, L.; Goda, S.; Kawanami, T.; Sawaki, T.; Sakai, T.; Tong, X.P.; Masaki, Y.; Fukushima, T.; Tanaka, M.; Mimori, T.; Tojo, H.; Bloom, E.T.; Okazaki, T.; Umehara, H.
Impaired TCR signaling through dysfunction of lipid rafts in sphingomyelin synthase 1 (SMS1)-knockdown T cells
Int. Immunol.
20
1427-1437
2008
Homo sapiens
brenda
Tafesse, F.G.; Huitema, K.; Hermansson, M.; van der Poel, S.; van den Dikkenberg, J.; Uphoff, A.; Somerharju, P.; Holthuis, J.C.
Both sphingomyelin synthases SMS1 and SMS2 are required for sphingomyelin homeostasis and growth in human HeLa cells
J. Biol. Chem.
282
17537-17547
2007
Homo sapiens, Mus musculus
brenda
Tani, M.; Kuge, O.
Sphingomyelin synthase 2 is palmitoylated at the COOH-terminal tail, which is involved in its localization in plasma membranes
Biochem. Biophys. Res. Commun.
381
328-332
2009
Homo sapiens
brenda
Vacaru, A.M.; Tafesse, F.G.; Ternes, P.; Kondylis, V.; Hermansson, M.; Brouwers, J.F.; Somerharju, P.; Rabouille, C.; Holthuis, J.C.
Sphingomyelin synthase-related protein SMSr controls ceramide homeostasis in the ER
J. Cell Biol.
185
1013-1027
2009
Homo sapiens
brenda
Ding, T.; Li, Z.; Hailemariam, T.; Mukherjee, S.; Maxfield, F.; Wu, M.; Jiang, X.
SMS overexpression and knockdown: Impact on cellular sphingomyelin and diacylglycerol metabolism, and cell apoptosis
J. Lipid Res.
49
376-385
2008
Homo sapiens
brenda
Ternes, P.; Brouwers, J.F.; van den Dikkenberg, J.; Holthuis, J.C.
Sphingomyelin synthase SMS2 displays dual activity as ceramide phosphoethanolamine synthase
J. Lipid Res.
50
2270-2277
2009
Homo sapiens
brenda
Chen, Y.; Yurek, D.A.; Yu, L.; Wang, H.; Ehsani, M.E.; Qian, Y.W.; Konrad, R.J.; Jiang, X.C.; Kuo, M.S.; Cao, G.; Wang, J.
Development of a quantitative biochemical and cellular sphingomyelin synthase assay using mass spectrometry
Anal. Biochem.
438
61-66
2013
Homo sapiens (Q86VZ5), Homo sapiens (Q8NHU3), Homo sapiens
brenda
Burns, T.A.; Subathra, M.; Signorelli, P.; Choi, Y.; Yang, X.; Wang, Y.; Villani, M.; Bhalla, K.; Zhou, D.; Luberto, C.
Sphingomyelin synthase 1 activity is regulated by the BCR-ABL oncogene
J. Lipid Res.
54
794-805
2013
Homo sapiens
brenda
Zhao, Y.R.; Dong, J.B.; Li, Y.; Wu, M.P.
Sphingomyelin synthase 2 over-expression induces expression of aortic inflammatory biomarkers and decreases circulating EPCs in ApoE KO mice
Life Sci.
90
867-873
2012
Homo sapiens
brenda
Yeang, C.; Ding, T.; Chirico, W.J.; Jiang, X.C.
Subcellular targeting domains of sphingomyelin synthase 1 and 2
Nutr. Metab.
8
89
2011
Homo sapiens (Q86VZ5), Mus musculus (Q9D4B1)
brenda
Qureshi, A.; Subathra, M.; Grey, A.; Schey, K.; Del Poeta, M.; Luberto, C.
Role of sphingomyelin synthase in controlling the antimicrobial activity of neutrophils against Cryptococcus neoformans
PLoS ONE
5
e15587
2010
Homo sapiens
brenda
Subathra, M.; Qureshi, A.; Luberto, C.
Sphingomyelin synthases regulate protein trafficking and secretion
PLoS ONE
6
e23644
2011
Homo sapiens, Rattus norvegicus
brenda
Barcelo-Coblijn, G.; Martin, M.L.; de Almeida, R.F.; Noguera-Salva, M.A.; Marcilla-Etxenike, A.; Guardiola-Serrano, F.; Lueth, A.; Kleuser, B.; Halver, J.E.; Escriba, P.V.
Sphingomyelin and sphingomyelin synthase (SMS) in the malignant transformation of glioma cells and in 2-hydroxyoleic acid therapy
Proc. Natl. Acad. Sci. USA
108
19569-19574
2011
Homo sapiens
brenda
Piotto, S.; Concilio, S.; Bianchino, E.; Iannelli, P.; Lopez, D.J.; Teres, S.; Ibarguren, M.; Barcelo-Coblijn, G.; Martin, M.L.; Guardiola-Serrano, F.; Alonso-Sande, M.; Funari, S.S.; Busquets, X.; Escriba, P.V.
Differential effect of 2-hydroxyoleic acid enantiomers on protein (sphingomyelin synthase) and lipid (membrane) targets
Biochim. Biophys. Acta
1838
1628-1637
2014
Homo sapiens
brenda
Li, Y.L.; Qi, X.Y.; Jiang, H.; Deng, X.D.; Dong, Y.P.; Ding, T.B.; Zhou, L.; Men, P.; Chu, Y.; Wang, R.X.; Jiang, X.C.; Ye, D.Y.
Discovery, synthesis and biological evaluation of 2-(4-(N-phenethylsulfamoyl)phenoxy)acetamides (SAPAs) as novel sphingomyelin synthase 1 inhibitors
Bioorg. Med. Chem.
23
6173-6184
2015
Homo sapiens (Q86VZ5)
brenda
Hu, S.; Ding, Y.; Song, D.; Chen, Q.; Yan, N.
Construction and identification of RNA interference vector of human sphingomyelin synthase
Fudan Univ. J. Med. Sci.
40
584-588
2013
Homo sapiens (Q86VZ5), Homo sapiens (Q8NHU3)
-
brenda
Thomaseth, C.; Weber, P.; Hamm, T.; Kashima, K.; Radde, N.
Modeling sphingomyelin synthase 1 driven reaction at the Golgi apparatus can explain data by inclusion of a positive feedback mechanism
J. Theor. Biol.
337
174-180
2013
Homo sapiens (Q86VZ5)
brenda
Hsiao, J.H.; Fu, Y.; Hill, A.F.; Halliday, G.M.; Kim, W.S.
Elevation in sphingomyelin synthase activity is associated with increases in amyloid-beta peptide generation
PLoS ONE
8
e74016
2013
Homo sapiens (Q86VZ5), Homo sapiens
brenda
Yukawa, T.; Nakahata, T.; Okamoto, R.; Ishichi, Y.; Miyamoto, Y.; Nishimura, S.; Oikawa, T.; Kubo, K.; Adachi, R.; Satomi, Y.; Nakakariya, M.; Amano, N.; Kamaura, M.; Matsunaga, N.
Discovery of 1,8-naphthyridin-2-one derivative as a potent and selective sphingomyelin synthase 2 inhibitor
Bioorg. Med. Chem.
28
115376
2020
Homo sapiens (Q86VZ5), Homo sapiens (Q8NHU3), Mus musculus (Q9D4B1)
brenda
Adachi, R.; Ogawa, K.; Matsumoto, S.; Satou, T.; Tanaka, Y.; Sakamoto, J.; Nakahata, T.; Okamoto, R.; Kamaura, M.; Kawamoto, T.
Discovery and characterization of selective human sphingomyelin synthase 2 inhibitors
Eur. J. Med. Chem.
136
283-293
2017
Homo sapiens (Q86VZ5), Homo sapiens (Q8NHU3), Homo sapiens
brenda
Li, Y.; Huang, T.; Lou, B.; Ye, D.; Qi, X.; Li, X.; Hu, S.; Ding, T.; Chen, Y.; Cao, Y.; Mo, M.; Dong, J.; Wei, M.; Chu, Y.; Li, H.; Jiang, X.; Cheng, N.; Zhou, L.
Discovery, synthesis and anti-atherosclerotic activities of a novel selective sphingomyelin synthase 2 inhibitor
Eur. J. Med. Chem.
163
864-882
2019
Homo sapiens (Q8NHU3)
brenda
Zhang, P.; Hua, L.; Hou, H.; Du, X.; He, Z.; Liu, M.; Hu, X.; Yan, N.
Sphingomyelin synthase 2 promotes H2O2-induced endothelial dysfunction by activating the Wnt/beta-catenin signaling pathway
Int. J. Mol. Med.
42
3344-3354
2018
Homo sapiens (Q8NHU3)
brenda
Gong, H.; Zhou, L.; Ye, D.; Gao, X.; Li, Y.; Qi, X.; Chu, Y.
Novel dual inhibitors of secretory phospholipase A2 and sphingomyelin synthase Design, synthesis and evaluation
Lett. Drug Des. Discov.
13
1025-1032
2016
Homo sapiens (Q8NHU3)
-
brenda
Li, X.; Luo, T.; Li, H.; Yan, N.
Sphingomyelin synthase 2 participate in the regulation of sperm motility and apoptosis
Molecules
25
4231
2020
Homo sapiens (Q8NHU3), Homo sapiens
brenda