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Information on EC 2.7.8.27 - sphingomyelin synthase
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EC Tree
2.7.8.27 sphingomyelin synthaseIUBMB Comments
The reaction can occur in both directions . This enzyme occupies a central position in sphingolipid and glycerophospholipid metabolism . Up- and down-regulation of its activity has been linked to mitogenic and pro-apoptotic signalling in a variety of mammalian cell types . Unlike EC 2.7.8.3, ceramide cholinephosphotransferase, CDP-choline cannot replace phosphatidylcholine as the donor of the phosphocholine moiety of sphingomyelin .
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Word Map
- 2.7.8.27
- sphingolipids
- sphingomyelinase
- diacylglycerol
- glucosylceramide
-
microdomains
- ceramidase
-
phosphatidylcholine-specific
- phosphoethanolamine
- pc-plc
- dihydroceramide
-
2-hydroxyoleic
- cert
- medicine
- tricyclodecan-9-yl-xanthogenate
- analysis
- drug development
- pharmacology
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
Reaction Schemes
Synonyms
sphingomyelin synthase, sm synthase, sgms1, sphingomyelin synthase 1, sphingomyelin synthase 2, sgms2, sphingomyelin-synthase, sm synthase 1, sphingomyelin synthases 1, sphingomyelin synthase-related protein, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
phosphatidylcholine:ceramide cholinephosphotransferase 1
phosphatidylcholine:ceramide cholinephosphotransferase 2
SGMS1
Sgms2
SM synthase
SMS
SMS1
SMS2
sphingomyelin synthase 1
sphingomyelin synthase 2
sphingomyelin-synthase
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
a ceramide + a phosphatidylcholine = a sphingomyelin + a 1,2-diacyl-sn-glycerol
-
-
-
-
a ceramide + a phosphatidylcholine = a sphingomyelin + a 1,2-diacyl-sn-glycerol
positive feedback mechanism from the products to the reactants, in vivo via protein kinase D and the ceramide transfer protein CERT, modeling
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SYSTEMATIC NAME
IUBMB Comments
ceramide:phosphatidylcholine cholinephosphotransferase
The reaction can occur in both directions [3]. This enzyme occupies a central position in sphingolipid and glycerophospholipid metabolism [4]. Up- and down-regulation of its activity has been linked to mitogenic and pro-apoptotic signalling in a variety of mammalian cell types [4]. Unlike EC 2.7.8.3, ceramide cholinephosphotransferase, CDP-choline cannot replace phosphatidylcholine as the donor of the phosphocholine moiety of sphingomyelin [2].
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CAS REGISTRY NUMBER
COMMENTARY
58703-97-2
-
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
6-((N-(7-nitrobenz-2-oxa-1,3-diazol-4-yl)amino)hexanoyl)-sphingosine + 1,2-dimyristoyl-sn-glycero-3-phosphocholine
N-(N-(7-nitro-2,1,3-benzoxadiazol-4-yl)-epsilon-aminohexanoyl)sphingosylphosphorylcholine + ?
-
-
-
-
?
6-((N-(7-nitrobenz-2-oxa-1,3-diazol-4-yl)amino)hexanoyl)sphingosine + phosphatidylcholine
N-hexanoyl-4-nitrobenz-2-oxa-1,3-diazole-sphingomyelin + 1,2-diacylglycerol
-
-
-
?
C17-ceramide + 1,2-dimyristoyl-rac-glycero-3-phosphocholine
C17-sphingomyelin + 1,2-dimyristoyl-rac-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
-
-
?
N-(6-((7-nitrobenz-2-oxa-1.3-diazol-4-yl)amino)hexanoyl)-sphingosine + a phosphatidylcholine
N-(6-((7-nitro-2-1,3-benzoxadiazol-4-yl)amino)hexanoyl)-sphingosine-1-phosphocholine + a 1,2-diacyl-sn-glycerol
i.e. C6-NBD-ceramide
i.e. C6-NBD-sphingomyelin or C6-NBDCerPCho
-
?
N-lauroyl-D-erythro-sphingosylphosphorylcholine + N-(6-[(7-nitro-benz-2-oxa-1,3-diazo-4-yl)amino]caproyl)-ceramide
?
-
i.e. lauroyl sphingomyelin and C6-NBD-ceramide
-
-
?
phosphatidylcholine + 6-((N-(7-nitrobenz-2-oxa-1,3-diazol-4-yl)amino)hexanoyl)sphingosine
N-hexanoyl-4-nitrobenz-2-oxa-1,3-diazole-sphingomyelin + 1,2-diacylglycerol
-
-
-
-
ir
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
-
-
-
?
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))
-
?
a ceramide + a phosphatidylcholine
a sphingomyelin + a 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
-
-
-
-
?
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 + 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
-
-
-
?
phosphatidylcholine + ceramide
sphingomyelin + 1,2-diacyl-sn-glycerol
-
-
-
?
phosphatidylcholine + ceramide
sphingomyelin + 1,2-diacyl-sn-glycerol
-
-
-
-
?
phosphatidylcholine + ceramide
sphingomyelin + diacylglycerol
-
-
-
?
phosphatidylcholine + ceramide
sphingomyelin + diacylglycerol
SMS2 is crucial to cellular lipid metabolism
-
-
?
additional information
?
-
-
synthesis of N-6[7-nitro-2,1,3-benzoxadiazol-4-yl]aminohexanoyl-phosphatidylcholine on the basolateral cell surface of MDCK cells occurs via the reverse reaction of a sphingomyelin synthase
-
-
?
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
-
-
?
additional information
?
-
SMS1 not only suppresses the effects of Bax overexpression, but it also blocks the deleterious effects of a number of other stresses, including hydrogen peroxide, osmotic stress, elevated temperature and exogenously supplied sphingolipids. Sphingomyelin synthase 1 likely prevents cell death by counteracting stress-mediated accumulation of endogenous sphingolipids
-
-
?
additional information
?
-
-
SMS1 not only suppresses the effects of Bax overexpression, but it also blocks the deleterious effects of a number of other stresses, including hydrogen peroxide, osmotic stress, elevated temperature and exogenously supplied sphingolipids. Sphingomyelin synthase 1 likely prevents cell death by counteracting stress-mediated accumulation of endogenous sphingolipids
-
-
?
additional information
?
-
-
SMS1 is located in the Golgi apparatus, where its two enzymatic products, sphingomyelin and diacylglycerol, play an important role in new lipid raft formation and secretory vesicle formation at the trans-Golgi network for transport to the plasma membrane, sphingomyelin synthesis through SMS1 depends on cholesterol homeostasis. S49AR cells are unable to synthesize sphingomyelin due to downregulated SMS1 expression
-
-
?
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
?
-
development of a HPLC-FLD method for real-time monitoring of relative SMS activity based on the measurement of 6-((N-(7-nitrobenz-2-oxa-1.3-diazol-4-yl)amino)hexanoyl)-sphingosine (C6-NBD-Cer) and 6-((N-(7-nitro-2-1,3-benzoxadiazol-4-yl)amino)hexanoyl)-sphingosine-1-phosphocholine (C6-NBDCerPCho) in plasma, which is then used to assess the SMS inhibitory activity of D2 in vivo, kinetics, overview
-
-
?
additional information
?
-
-
highly purified sphingomyelin synthase preparation also shows neutral sphingomyelinase activity
-
-
?
additional information
?
-
-
SMS2 may play a crucial role in the lipid metabolism in arosome formation and the plasma membrane restructuring from late round spermatids to early elongating spermatids
-
-
?
additional information
?
-
SMS2 may play a crucial role in the lipid metabolism in arosome formation and the plasma membrane restructuring from late round spermatids to early elongating spermatids
-
-
?
additional information
?
-
-
SMS1 is a key enzyme in the sphingomyelin cycle, metabolites of the cycle play an important role in neuronal death after ischemia, mechanism underlying cerebral ischemia, overview
-
-
?
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
6-((N-(7-nitrobenz-2-oxa-1,3-diazol-4-yl)amino)hexanoyl)-sphingosine + 1,2-dimyristoyl-sn-glycero-3-phosphocholine
N-(N-(7-nitro-2,1,3-benzoxadiazol-4-yl)-epsilon-aminohexanoyl)sphingosylphosphorylcholine + ?
-
-
-
-
?
phosphatidylcholine + ceramide
sphingomyelin + 1,2-diacyl-sn-glycerol
-
-
-
?
phosphatidylcholine + ceramide
sphingomyelin + diacylglycerol
SMS2 is crucial to cellular lipid metabolism
-
-
?
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
-
-
-
?
a ceramide + a phosphatidylcholine
a sphingomyelin + a 1,2-diacyl-sn-glycerol
-
-
-
?
ceramide + phosphatidylcholine
sphingomyelin + 1,2-diacyl-sn-glycerol
-
the enzyme restores homeostasis between sphingomyelin and ceramide pools
-
-
?
additional information
?
-
-
synthesis of N-6[7-nitro-2,1,3-benzoxadiazol-4-yl]aminohexanoyl-phosphatidylcholine on the basolateral cell surface of MDCK cells occurs via the reverse reaction of a sphingomyelin synthase
-
-
?
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
?
-
SMS1 not only suppresses the effects of Bax overexpression, but it also blocks the deleterious effects of a number of other stresses, including hydrogen peroxide, osmotic stress, elevated temperature and exogenously supplied sphingolipids. Sphingomyelin synthase 1 likely prevents cell death by counteracting stress-mediated accumulation of endogenous sphingolipids
-
-
?
additional information
?
-
-
SMS1 not only suppresses the effects of Bax overexpression, but it also blocks the deleterious effects of a number of other stresses, including hydrogen peroxide, osmotic stress, elevated temperature and exogenously supplied sphingolipids. Sphingomyelin synthase 1 likely prevents cell death by counteracting stress-mediated accumulation of endogenous sphingolipids
-
-
?
additional information
?
-
-
SMS1 is located in the Golgi apparatus, where its two enzymatic products, sphingomyelin and diacylglycerol, play an important role in new lipid raft formation and secretory vesicle formation at the trans-Golgi network for transport to the plasma membrane, sphingomyelin synthesis through SMS1 depends on cholesterol homeostasis. S49AR cells are unable to synthesize sphingomyelin due to downregulated SMS1 expression
-
-
?
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
?
-
-
SMS2 may play a crucial role in the lipid metabolism in arosome formation and the plasma membrane restructuring from late round spermatids to early elongating spermatids
-
-
?
additional information
?
-
SMS2 may play a crucial role in the lipid metabolism in arosome formation and the plasma membrane restructuring from late round spermatids to early elongating spermatids
-
-
?
additional information
?
-
-
SMS1 is a key enzyme in the sphingomyelin cycle, metabolites of the cycle play an important role in neuronal death after ischemia, mechanism underlying cerebral ischemia, overview
-
-
?
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Mn2+
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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; 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
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-(4-(N-phenethylsulfamoyl)phenoxy)-N-(2-(trifluoromethoxy)phenyl)acetamide
-
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
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-(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; 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; more than 100fold selectivity for isoform SGMS2 over SGMS1
N-(4-fluoro-2-methoxyphenyl)-2-(4-(N-phenethylsulfamoyl)phenoxy)acetamide
-
N-[(4-bromophenyl)methyl]-2-[4-[(2-phenylethyl)sulfamoyl]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
tert-butyl 4-(3-((3-((3,5-dimethoxybenzyl)(methyl)carbamoyl)-1-methyl-2-oxo-1,2-dihydroquinolin-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-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-dihydro-1,8-naphthyridin-4-yl)oxy)propyl)piperidine-1-carboxylate
-
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; potent and selective inhibitor of isoform SGMS2. A repeated treatment in mice leads to significant reduction in hepatic sphingomyelin levels
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
-
2-(2-(benzyloxy)phenyl)-2-(phenylamino) acetonitrile
i.e. D2, development of a HPLC-FLD method for real-time monitoring of relative SMS activity based on the measurement of C6-NBD-Cer and C6-NBDCerPCho in plasma, which is then used to assess the SMS inhibitory activity of D2 in vivo, overview
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-((3-((3,5-bis(trifluoromethyl)benzyl)(methyl)carbamoyl)-1-methyl-2-oxo-1,2-dihydroquinolin-4-yl)oxy)propyl)piperidine-1-carboxylate
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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
4-(3-(benzyloxy)pyrrolidin-1-yl)-N-(3,5-bis(trifluoromethyl)benzyl)-N,1-dimethyl-2-oxo-1,2-dihydroquinoline-3-carboxamide
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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-(4,4,4-trifluorobutoxy)-1,2-dihydroquinoline-3-carboxamide
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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-dihydro-1,8-naphthyridin-4-yl)oxy)propyl)piperidine-1-carboxylate
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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
tert-butyl 4-(3-((3-((3,5-dimethoxybenzyl)(methyl)carbamoyl)-1-methyl-2-oxo-1,2-dihydroquinolin-4-yl)oxy)propyl)piperidine-1-carboxylate