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Information on EC 2.4.1.80 - ceramide glucosyltransferase and Organism(s) Homo sapiens and UniProt Accession Q16739

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EC Tree
     2 Transferases
         2.4 Glycosyltransferases
             2.4.1 Hexosyltransferases
                2.4.1.80 ceramide glucosyltransferase
IUBMB Comments
Sphingosine and dihydrosphingosine can also act as acceptors; CDP-glucose can act as donor.
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This record set is specific for:
Homo sapiens
UNIPROT: Q16739
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Word Map
The taxonomic range for the selected organisms is: Homo sapiens
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
Synonyms
glccer synthase, ceramide glucosyltransferase, glct-1, glccers, udp-glucose ceramide glucosyltransferase, udp-glucose:ceramide glucosyltransferase, cgt-3, cgt-1, udp-glucose ceramide glycosyltransferase, cgt-2, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
glucosylceramide synthase
-
UDP-glucose: ceramide glucosyltransferase
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ceramide:UDP-glucose glucosyltransferase
-
-
-
-
ceramide:UDPGlc glucosyltransferase
-
-
-
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GlcCer synthase
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GlcCerS
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GlcT-1
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glucosylceramide synthase
glucosyltransferase, uridine diphosphoglucose-ceramide
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-
-
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UDP glucose-ceramide glucosyltransferase
-
-
-
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UDP-glucose ceramide glucosyltransferase
-
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UDP-glucose ceramide glycosyltransferase
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UDP-glucose:ceramide glucosyltransferase
uridine diphosphoglucose-ceramide glucosyltransferase
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-
-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
hexosyl group transfer
-
-
-
-
PATHWAY SOURCE
PATHWAYS
-
-, -, -, -, -
SYSTEMATIC NAME
IUBMB Comments
UDP-glucose:N-acylsphingosine D-glucosyltransferase
Sphingosine and dihydrosphingosine can also act as acceptors; CDP-glucose can act as donor.
CAS REGISTRY NUMBER
COMMENTARY hide
37237-44-8
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SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
UDP + N-{6-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]hexanoyl}sphingosine
UDP + ?
show the reaction diagram
-
-
-
?
UDP-glucose + 6-(((N-7-nitrobenz-2-oxa-1,3-diazol-4yl)amino)caproyl)sphingosine
UDP + ?
show the reaction diagram
-
-
-
?
UDP-glucose + an N-acylsphingosine
UDP + a D-glucosyl-N-acylsphingosine
show the reaction diagram
-
-
-
?
UDP-glucose + N-acylsphingosine
UDP + D-glucosyl-N-acylsphingosine
show the reaction diagram
UDP-glucose + N-octanoyl sphingosine
UDP + D-glucosyl-N-octanoyl sphingosine
show the reaction diagram
best substrate
-
?
UDP-glucose + C6-ceramide
UDP + C6-glucosylceramide
show the reaction diagram
-
with fluorescent NBD C6-ceramide resulting in NBD C6-glucosylceramide direct quantification of ceramide glycosylation catalyzed by GCS in cells and in tissues are possible
-
-
?
UDP-glucose + C6-ceramide
UDP + glucosyl-C6-ceramide
show the reaction diagram
-
-
-
-
?
UDP-glucose + ceramide
UDP + glucosylceramide
show the reaction diagram
UDP-glucose + N-6-[(7-nitrobenzo-2-oxa-1,3-diazol-4-yl)amino]hexanoyl-4-D-erythro-sphingosine
UDP + N-(6-((4-nitrobenz-2-oxa-1,3-diazol-7-yl)amino)caproyl)-O1-D-glucosyl-sphingosine
show the reaction diagram
-
-
-
-
?
UDP-glucose + N-acylsphingosine
UDP + D-glucosyl-N-acylsphingosine
show the reaction diagram
additional information
?
-
NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
UDP-glucose + an N-acylsphingosine
UDP + a D-glucosyl-N-acylsphingosine
show the reaction diagram
-
-
-
?
UDP-glucose + N-acylsphingosine
UDP + D-glucosyl-N-acylsphingosine
show the reaction diagram
UDP-glucose + ceramide
UDP + glucosylceramide
show the reaction diagram
-
-
glucosylceramide is a precursor for synthesis of a multitude of higher sphingolipids
-
?
UDP-glucose + N-acylsphingosine
UDP + D-glucosyl-N-acylsphingosine
show the reaction diagram
additional information
?
-
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enzyme decreases apoptosis and induces multidrug resistance, functional interaction with RTN-1C modulates enzyme activity and regulates chemotherapeutic-induced apoptosis in neuroepithelioma cells
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-
?
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(+/-)-threo-1-phenyl-2-decanoylamino-3-morpholino-1-propanol
-
(2R,3R,4R,5S)-1-(2-hydroxyethyl)-2-(hydroxymethyl)piperidine-3,4,5-triol
i.e. miglitol
(2R,3R,4R,5S)-1-(5-[[3',5'-bis(trifluoromethyl)[1,1'-biphenyl]-4-yl]methoxy]pentyl)-2-(hydroxymethyl)piperidine-3,4,5-triol
-
(2R,3R,4R,5S)-1-(5-[[4-(2,3-dihydro-1,4-benzodioxin-6-yl)phenyl]methoxy]pentyl)-2-(hydroxymethyl)piperidine-3,4,5-triol
-
(2R,3R,4R,5S)-1-(5-[[4-(2-fluoropyridin-4-yl)phenyl]methoxy]pentyl)-2-(hydroxymethyl)piperidine-3,4,5-triol
-
(2R,3R,4R,5S)-1-(5-[[4-(2H-1,3-benzodioxol-5-yl)phenyl]methoxy]pentyl)-2-(hydroxymethyl)piperidine-3,4,5-triol
-
(2R,3R,4R,5S)-1-(5-[[4-(6-fluoropyridin-3-yl)phenyl]methoxy]pentyl)-2-(hydroxymethyl)piperidine-3,4,5-triol
-
(2R,3R,4R,5S)-1-butyl-2-(hydroxymethyl)piperidine-3,4,5-triol
i.e. miglustat or Zavesca
(2R,3R,4R,5S)-1-[5-(benzyloxy)pentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol
-
(2R,3R,4R,5S)-1-[5-(cyclohexylmethoxy)pentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol
-
(2R,3R,4R,5S)-1-[5-(hexyloxy)pentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol
-
(2R,3R,4R,5S)-1-[5-([(3R,10S,13S,17R)-10,13-dimethyl-17-[(2S)-7-methyloctan-2-yl]-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy)pentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol
-
(2R,3R,4R,5S)-1-[5-[(1R)-1-([1,1'-biphenyl]-4-yl)ethoxy]pentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol
-
(2R,3R,4R,5S)-1-[5-[(1S)-1-([1,1'-biphenyl]-4-yl)ethoxy]pentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol
-
(2R,3R,4R,5S)-1-[5-[(2'-fluoro[1,1'-biphenyl]-4-yl)methoxy]pentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol
-
(2R,3R,4R,5S)-1-[5-[(2-fluoro[1,1'-biphenyl]-4-yl)methoxy]pentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol
-
(2R,3R,4R,5S)-1-[5-[(3'-fluoro[1,1'-biphenyl]-4-yl)methoxy]pentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol
-
(2R,3R,4R,5S)-1-[5-[(3-fluoro[1,1'-biphenyl]-4-yl)methoxy]pentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol
-
(2R,3R,4R,5S)-1-[5-[(4'-chloro[1,1'-biphenyl]-4-yl)methoxy]pentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol
-
(2R,3R,4R,5S)-1-[5-[(4'-fluoro[1,1'-biphenyl]-4-yl)methoxy]pentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol
-
(2R,3R,4R,5S)-1-[5-[(4,8-dihydropyren-1-yl)methoxy]pentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol
-
(2R,3R,4R,5S)-1-[5-[(5,8-dihydronaphthalen-2-yl)methoxy]pentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol
-
(2R,3R,4R,5S)-1-[5-[([1,1'-biphenyl]-2-yl)methoxy]pentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol
-
(2R,3R,4R,5S)-1-[5-[([1,1'-biphenyl]-3-yl)methoxy]pentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol
-
(2R,3R,4R,5S)-1-[5-[([1,1'-biphenyl]-4-yl)methoxy]-2,2-difluoropentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol
-
(2R,3R,4R,5S)-1-[5-[([1,1'-biphenyl]-4-yl)methoxy]-4,4-difluoropentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol
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(2R,3R,4R,5S)-1-[5-[([1,1'-biphenyl]-4-yl)methoxy]pentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol
-
(2R,3R,4R,5S)-2-(hydroxymethyl)-1-((adamantylmethoxy)hexyl)piperidine-3,4,5-triol
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(2R,3R,4R,5S)-2-(hydroxymethyl)-1-(5-(adamantylmethoxy)pentyl)piperidine-3,4,5-triol
i.e. AMP-DNM
(2R,3R,4R,5S)-2-(hydroxymethyl)-1-(5-[[(2E,6E)-3,7,10-trimethylundeca-2,6,9-trien-1-yl]oxy]pentyl)piperidine-3,4,5-triol
-
(2R,3R,4R,5S)-2-(hydroxymethyl)-1-(5-[[2-(trifluoromethyl)[1,1'-biphenyl]-4-yl]methoxy]pentyl)piperidine-3,4,5-triol
-
(2R,3R,4R,5S)-2-(hydroxymethyl)-1-(5-[[3-(trifluoromethyl)[1,1'-biphenyl]-4-yl]methoxy]pentyl)piperidine-3,4,5-triol
-
(2R,3R,4R,5S)-2-(hydroxymethyl)-1-(5-[[4'-(trifluoromethyl)[1,1'-biphenyl]-4-yl]methoxy]pentyl)piperidine-3,4,5-triol
-
(2R,3R,4R,5S)-2-(hydroxymethyl)-1-(5-[[4-(2,3,4,5-tetrahydro-1,6-benzodioxocin-8-yl)phenyl]methoxy]pentyl)piperidine-3,4,5-triol
-
(2R,3R,4R,5S)-2-(hydroxymethyl)-1-(5-[[4-(pyridin-3-yl)phenyl]methoxy]pentyl)piperidine-3,4,5-triol
-
(2R,3R,4R,5S)-2-(hydroxymethyl)-1-(5-[[4-(pyridin-4-yl)phenyl]methoxy]pentyl)piperidine-3,4,5-triol
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(2R,3R,4R,5S)-2-(hydroxymethyl)-1-(5-[[4-(pyrimidin-5-yl)phenyl]methoxy]pentyl)piperidine-3,4,5-triol
-
(2R,3R,4R,5S)-2-(hydroxymethyl)-1-(6-(adamantylhexyl)hexyl)piperidine-3,4,5-triol
-
(2R,3R,4R,5S)-2-(hydroxymethyl)-1-(adamantylhept-6-en-1-yl)piperidine-3,4,5-triol
-
(2R,3R,4R,5S)-2-(hydroxymethyl)-1-(adamantylhexyl)piperidine-3,4,5-triol
-
(2R,3R,4R,5S)-2-(hydroxymethyl)-1-[5-[(2'-methoxy[1,1'-biphenyl]-4-yl)methoxy]pentyl]piperidine-3,4,5-triol
-
(2R,3R,4R,5S)-2-(hydroxymethyl)-1-[5-[(2'-methyl[1,1'-biphenyl]-4-yl)methoxy]pentyl]piperidine-3,4,5-triol
-
(2R,3R,4R,5S)-2-(hydroxymethyl)-1-[5-[(3'-methoxy[1,1'-biphenyl]-4-yl)methoxy]pentyl]piperidine-3,4,5-triol
-
(2R,3R,4R,5S)-2-(hydroxymethyl)-1-[5-[(3'-methyl[1,1'-biphenyl]-4-yl)methoxy]pentyl]piperidine-3,4,5-triol
-
(2R,3R,4R,5S)-2-(hydroxymethyl)-1-[5-[(4'-methoxy[1,1'-biphenyl]-4-yl)methoxy]pentyl]piperidine-3,4,5-triol
-
(2R,3R,4R,5S)-2-(hydroxymethyl)-1-[5-[(4'-methyl[1,1'-biphenyl]-4-yl)methoxy]pentyl]piperidine-3,4,5-triol
-
(2R,3R,4R,5S)-2-(hydroxymethyl)-1-[5-[(5-phenylpyridin-2-yl)methoxy]pentyl]piperidine-3,4,5-triol
-
(2R,3R,4R,5S)-2-(hydroxymethyl)-1-[5-[(phenanthren-9-yl)methoxy]pentyl]piperidine-3,4,5-triol
-
(2S,3R,4R,5S)-1-[5-(benzyloxy)pentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol
-
(2S,3R,4R,5S)-1-[5-(cyclohexylmethoxy)pentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol
-
(2S,3R,4R,5S)-1-[5-(hexyloxy)pentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol
-
(2S,3R,4R,5S)-1-[5-([(3R,10S,13S,17R)-10,13-dimethyl-17-[(2S)-7-methyloctan-2-yl]-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy)pentyl]-2-(hydroxymethyl)piperidine-3,4,5-trio
-
(2S,3R,4R,5S)-1-[5-[(1R)-1-([1,1'-biphenyl]-4-yl)ethoxy]pentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol
-
(2S,3R,4R,5S)-1-[5-[(1S)-1-([1,1'-biphenyl]-4-yl)ethoxy]pentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol
-
(2S,3R,4R,5S)-1-[5-[(2-fluoro[1,1'-biphenyl]-4-yl)methoxy]pentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol
-
(2S,3R,4R,5S)-1-[5-[(3-fluoro[1,1'-biphenyl]-4-yl)methoxy]pentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol
-
(2S,3R,4R,5S)-1-[5-[(4,8-dihydropyren-1-yl)methoxy]pentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol
-
(2S,3R,4R,5S)-1-[5-[(5,8-dihydronaphthalen-2-yl)methoxy]pentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol
-
(2S,3R,4R,5S)-1-[5-[([1,1'-biphenyl]-2-yl)methoxy]pentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol
-
(2S,3R,4R,5S)-1-[5-[([1,1'-biphenyl]-3-yl)methoxy]pentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol
-
(2S,3R,4R,5S)-1-[5-[([1,1'-biphenyl]-4-yl)methoxy]-2,2-difluoropentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol
-
(2S,3R,4R,5S)-1-[5-[([1,1'-biphenyl]-4-yl)methoxy]-4,4-difluoropentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol
-
(2S,3R,4R,5S)-1-[5-[([1,1'-biphenyl]-4-yl)methoxy]pentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol
-
(2S,3R,4R,5S)-2-(hydroxymethyl)-1-(5-(adamantylmethoxy)pentyl)piperidine-3,4,5-triol
i.e. ido-AMP-DNM
(2S,3R,4R,5S)-2-(hydroxymethyl)-1-(5-[[(2E,6E)-3,7,10-trimethylundeca-2,6,9-trien-1-yl]oxy]pentyl)piperidine-3,4,5-triol
-
(2S,3R,4R,5S)-2-(hydroxymethyl)-1-(5-[[2-(trifluoromethyl)[1,1'-biphenyl]-4-yl]methoxy]pentyl)piperidine-3,4,5-triol
-
(2S,3R,4R,5S)-2-(hydroxymethyl)-1-(5-[[3-(trifluoromethyl)[1,1'-biphenyl]-4-yl]methoxy]pentyl)piperidine-3,4,5-triol
-
(2S,3R,4R,5S)-2-(hydroxymethyl)-1-(6-(adamantylmethoxy)hexyl)piperidine-3,4,5-triol
-
(2S,3R,4R,5S)-2-(hydroxymethyl)-1-(6-adamantyloxyhexyl)piperidine-3,4,5-triol
-
(2S,3R,4R,5S)-2-(hydroxymethyl)-1-adamantylhexylpiperidine-3,4,5-triol
-
(2S,3R,4R,5S)-2-(hydroxymethyl)-1-[(6Z)-7-adamantylhept-6-en-1-yl]piperidine-3,4,5-triol
-
(2S,3R,4R,5S)-2-(hydroxymethyl)-1-[5-[(phenanthren-9-yl)methoxy]pentyl]piperidine-3,4,5-triol
-
4'-[([5-[(2R,3R,4R,5S)-3,4,5-trihydroxy-2-(hydroxymethyl)piperidin-1-yl]pentyl]oxy)methyl][1,1'-biphenyl]-2-carbonitrile
-
4'-[([5-[(2R,3R,4R,5S)-3,4,5-trihydroxy-2-(hydroxymethyl)piperidin-1-yl]pentyl]oxy)methyl][1,1'-biphenyl]-3-carbonitrile
-
4'-[([5-[(2R,3R,4R,5S)-3,4,5-trihydroxy-2-(hydroxymethyl)piperidin-1-yl]pentyl]oxy)methyl][1,1'-biphenyl]-4-carbonitrile
-
D-threo-1-phenyl-2-(decanoylamino)-3-morpholino-1-propanol-HCl
DL-erythro-1-phenyl-2-decanoylamino-3-morpholino-1-propanol
the enzyme GCS inhibitor causes cytotoxic, antiproliferative, antiangiogenic and tumor-volume-reducing effects, modulating drug responses in cell lines both cytodestructive (as a drug sensitizer) and cytoprotective, effect on cell survival, overview. The inhibitor is not suitable to deplete cells of the neolacto glycosphingolipid series
-
DL-threo-1-phenyl-2-palmitoylamino-3-morpholino-1-propanol
the enzyme GCS inhibitor causes cytotoxic, antiproliferative, antiangiogenic and tumor-volume-reducing effects, modulating drug responses in cell lines both cytodestructive (as a drug sensitizer) and cytoprotective, effect on cell survival, overview. The inhibitor is not suitable to deplete cells of the neolacto glycosphingolipid series
eliglustat
-
ethyl-2-amino-6-bromo-4-(1-cyano-2-ethoxy-2-oxoethyl)-4H-chromene-3-carboxylate
i.e. HA14-1, a reversible small molecule Bcl-2 inhibitor that also inhibits GlcT-1 enzyme activity. HA14-1 is a competitive and mixed-type inhibitor with respect to C6-NBD-ceramide and UDP-glucose, respectively. HA-14 does not possess structural homology with the substrates UDP-glucose and ceramide. Possible binding of GlcT-1 to Bcl-2
N-adamantanemethoxypentyldeoxynojirimycin
-
N-adamantyl-6-[(2R,3R,4R,5S)-3,4,5-trihydroxy-2-(hydroxymethyl)piperidin-1-yl]hexanamide
-
N-adamantyl-6-[(2S,3R,4R,5S)-3,4,5-trihydroxy-2-(hydroxymethyl)piperidin-1-yl]hexanamide
-
N-butyldeoxynojirimycin
N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-1-hydroxy-3-(morpholin-4-yl)propan-2-yl]-2-(4-methoxyphenoxy)acetamide
-
N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-1-hydroxy-3-(morpholin-4-yl)propan-2-yl]-5-(adamantylmethoxy)pentanamide
-
N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-1-hydroxy-3-(morpholin-4-yl)propan-2-yl]nonanamide
-
N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-1-hydroxy-3-(piperidin-1-yl)propan-2-yl]-2-(4-methoxyphenoxy)acetamide
-
N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-1-hydroxy-3-(piperidin-1-yl)propan-2-yl]-5-(adamantylmethoxy)pentanamide
-
N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-1-hydroxy-3-(piperidin-1-yl)propan-2-yl]nonanamide
-
N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-1-hydroxy-3-(pyrrolidin-1-yl)propan-2-yl]-2-(4-methoxyphenoxy)acetamide
-
N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-1-hydroxy-3-(pyrrolidin-1-yl)propan-2-yl]-5(adamantylmethoxy)pentanamide
-
N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-1-hydroxy-3-(pyrrolidin-1-yl)propan-2-yl]nonanamide
-
N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-1-hydroxy-3-[(2R,3R,4R,5S)-3,4,5-trihydroxy-2-(hydroxymethyl)piperidin-1-yl]propan-2-yl]-2-(4-methoxyphenoxy)acetamide
-
N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-1-hydroxy-3-[(2R,3R,4R,5S)-3,4,5-trihydroxy-2-(hydroxymethyl)piperidin-1-yl]propan-2-yl]-5-(adamantylmethoxy)pentanamide
-
N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-1-hydroxy-3-[(2R,3R,4R,5S)-3,4,5-trihydroxy-2-(hydroxymethyl)piperidin-1-yl]propan-2-yl]nonanamide
-
N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-1-hydroxy-3-[(2R,3S,4R,5S)-3,4,5-trihydroxy-2-(hydroxymethyl)piperidin-1-yl]propan-2-yl]-2-(4-methoxyphenoxy)acetamide
-
N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-1-hydroxy-3-[(2R,3S,4R,5S)-3,4,5-trihydroxy-2-(hydroxymethyl)piperidin-1-yl]propan-2-yl]-5-(adamantylmethoxy)pentanamide
-
N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-1-hydroxy-3-[(2R,3S,4R,5S)-3,4,5-trihydroxy-2-(hydroxymethyl)piperidin-1-yl]propan-2-yl]nonanamide
-
N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-1-hydroxy-3-[(2S,3R,4R,5S)-3,4,5-trihydroxy-2-(hydroxymethyl)piperidin-1-yl]propan-2-yl]-2-(4-methoxyphenoxy)acetamide
-
N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-1-hydroxy-3-[(2S,3R,4R,5S)-3,4,5-trihydroxy-2-(hydroxymethyl)piperidin-1-yl]propan-2-yl]-5-(adamantylmethoxy)pentanamide
-
N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-1-hydroxy-3-[(2S,3R,4R,5S)-3,4,5-trihydroxy-2-(hydroxymethyl)piperidin-1-yl]propan-2-yl]nonanamide
-
N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-1-hydroxy-3-[(2S,3S,4R,5S)-3,4,5-trihydroxy-2-(hydroxymethyl)piperidin-1-yl]propan-2-yl]-2-(4-methoxyphenoxy)acetamide
-
N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-1-hydroxy-3-[(2S,3S,4R,5S)-3,4,5-trihydroxy-2-(hydroxymethyl)piperidin-1-yl]propan-2-yl]-5-(adamantylmethoxy)pentanamide
-
N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-1-hydroxy-3-[(2S,3S,4R,5S)-3,4,5-trihydroxy-2-(hydroxymethyl)piperidin-1-yl]propan-2-yl]nonanamide
-
N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-3-[(2R,3R,4R)-3,4-dihydroxy-2-(hydroxymethyl)pyrrolidin-1-yl]-1-hydroxypropan-2-yl]-2-(4-methoxyphenoxy)acetamide
-
N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-3-[(2R,3R,4R)-3,4-dihydroxy-2-(hydroxymethyl)pyrrolidin-1-yl]-1-hydroxypropan-2-yl]-5-(adamantylmethoxy)pentanamide
-
N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-3-[(2R,3R,4R)-3,4-dihydroxy-2-(hydroxymethyl)pyrrolidin-1-yl]-1-hydroxypropan-2-yl]nonanamide
-
N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-3-[(2R,3R,4S)-3,4-dihydroxy-2-(hydroxymethyl)pyrrolidin-1-yl]-1-hydroxypropan-2-yl]-2-(4-methoxyphenoxy)acetamide
-
N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-3-[(2R,3R,4S)-3,4-dihydroxy-2-(hydroxymethyl)pyrrolidin-1-yl]-1-hydroxypropan-2-yl]-5-(adamantylmethoxy)pentanamide
-
N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-3-[(2R,3R,4S)-3,4-dihydroxy-2-(hydroxymethyl)pyrrolidin-1-yl]-1-hydroxypropan-2-yl]nonanamide
-
N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-3-[(2R,3S,4R)-3,4-dihydroxy-2-(hydroxymethyl)pyrrolidin-1-yl]-1-hydroxypropan-2-yl]-2-(4-methoxyphenoxy)acetamide
-
N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-3-[(2R,3S,4R)-3,4-dihydroxy-2-(hydroxymethyl)pyrrolidin-1-yl]-1-hydroxypropan-2-yl]-5-(adamantylmethoxy)pentanamide
-
N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-3-[(2R,3S,4R)-3,4-dihydroxy-2-(hydroxymethyl)pyrrolidin-1-yl]-1-hydroxypropan-2-yl]nonanamide
-
N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-3-[(2R,3S,4S)-3,4-dihydroxy-2-(hydroxymethyl)pyrrolidin-1-yl]-1-hydroxypropan-2-yl]-2-(4-methoxyphenoxy)acetamide
-
N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-3-[(2R,3S,4S)-3,4-dihydroxy-2-(hydroxymethyl)pyrrolidin-1-yl]-1-hydroxypropan-2-yl]-5-(adamantylmethoxy)pentanamide
-
N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-3-[(2R,3S,4S)-3,4-dihydroxy-2-(hydroxymethyl)pyrrolidin-1-yl]-1-hydroxypropan-2-yl]nonanamide
-
N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-3-[(2S,3R,4S)-3,4-dihydroxy-2-(hydroxymethyl)pyrrolidin-1-yl]-1-hydroxypropan-2-yl]-2-(4-methoxyphenoxy)acetamide
-
N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-3-[(2S,3R,4S)-3,4-dihydroxy-2-(hydroxymethyl)pyrrolidin-1-yl]-1-hydroxypropan-2-yl]-5-(adamantylmethoxy)pentanamide
-
N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-3-[(2S,3R,4S)-3,4-dihydroxy-2-(hydroxymethyl)pyrrolidin-1-yl]-1-hydroxypropan-2-yl]nonanamide
-
N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-3-[(2S,3S,4S)-3,4-dihydroxy-2-(hydroxymethyl)pyrrolidin-1-yl]-1-hydroxypropan-2-yl]-2-(4-methoxyphenoxy)acetamide
-
N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-3-[(2S,3S,4S)-3,4-dihydroxy-2-(hydroxymethyl)pyrrolidin-1-yl]-1-hydroxypropan-2-yl]-5-(adamantylmethoxy)pentanamide
-
N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-3-[(2S,3S,4S)-3,4-dihydroxy-2-(hydroxymethyl)pyrrolidin-1-yl]-1-hydroxypropan-2-yl]nonanamide
-
(1R)-1-C-octyl-N-octyl-1,5-dideoxy-1,5-imino-D-glucitol
-
-
(1R)-N-butyl-1-C-butyl-1,5-dideoxy-1,5-imino-D-glucitol
-
-
(1S)-1-C-[5-(adamantan-1-yl-methoxy)-pentyl]-1-deoxynojirimycin
-
-
(1S)-N-butyl-1-C-[5-(adamantan-1-yl-methoxy)-pentyl]-1-deoxynojirimycin
-
-
(D-threo)-1-(3',4'-ethylenedioxy)phenyl-2-palmitoylamino-3-pyrrolidino-1-propanol
-
the inhibitor is abolutely specific for the recombinant human enzyme and does not affect recombinant non-human enzymes from Gossypium arboreum, Caenorhabditis elegans, Aspergillus nidulans, Candida albicans, Pichia pastoris, Ustilago maydis, or Agrobacterium tumefaciens
(D-threo)-1-phenyl-2-decanoylamino-3-morpholino-1-propanol
-
specific inhibitor
1-phenyl-2-decanoylamino-3-morpholino-1-propanol
-
-
arsenic trioxide
-
treatment of a human acute promyelocytic leukemia cell line (NB4) and adult T-cell leukemia/lymphoma (ATL) derived cells with arsenic trioxide induces accumulation of cytoxic levels of ceramide which results from de novo ceramide synthesis and inhibition of glucosylceramide synthase activity
CDP-glucose
slight inhibition
D-threo-1-phenyl-2-(decanoylamino)-3-morpholino-1-propanol-HCl
-
D-threo-2-palmitoylamino-3-pyrrolidino-1-propanol
-
-
doxorubicin
N-butyl 1-deoxynojirimycin
-
-
N-butyl-2,4-di-O-butyl-1,5-dideoxy-1,5-imino-D-glucitol
-
1 mM, 29% inhibition
N-octyl-2-O-octyl-1,5-dideoxy-1,5-imino-D-glucitol
-
-
N-octyl-4-O-octyl-1,5-dideoxy-1,5-imino-D-glucitol
-
-
N-[5-(adamantan-1-yl-methoxy)-pentyl]-1-deoxynojirimycin
-
-
threo-1-phenyl-2-decanoyl-amino-3-morpholino-1-propanol
-
inhibition at 0.005 mM
Tris
58% loss of activity at 0.2 M
additional information
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
c-Fos
-
activity of glucosylceramide synthase is around 5fold higher in presence of high c-Fos levels, induced by nerve growth factor NGF, addition of c-Fos mRNA ASO, which specifically blocks c-Fos expression abolished the induction of glucosylceramide synthase by NGF
-
detergent
-
-
-
NAD+
stimulation, best at 2 mM
NADH
stimulation
NADP+
stimulation
NADPH
stimulation
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.04055
C6-ceramide
-
in tumor of NCI/ADR-RES
0.013 - 0.02
N-(6-((4-nitrobenz-2-oxa-1,3-diazol-7-yl)amino)caproyl)-O1-D-glucosyl-sphingosine
0.03877
NBD C6-ceramide
-
substrate is fluorescent
0.0069 - 0.0079
UDP-glucose
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0045
ethyl-2-amino-6-bromo-4-(1-cyano-2-ethoxy-2-oxoethyl)-4H-chromene-3-carboxylate
pH 7.5, 30°C
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.00002
(2R,3R,4R,5S)-1-(5-[[3',5'-bis(trifluoromethyl)[1,1'-biphenyl]-4-yl]methoxy]pentyl)-2-(hydroxymethyl)piperidine-3,4,5-triol
Homo sapiens
pH and temperature not specified in the publication
0.00004
(2R,3R,4R,5S)-1-(5-[[4-(2,3-dihydro-1,4-benzodioxin-6-yl)phenyl]methoxy]pentyl)-2-(hydroxymethyl)piperidine-3,4,5-triol
Homo sapiens
pH and temperature not specified in the publication
0.00015
(2R,3R,4R,5S)-1-(5-[[4-(2-fluoropyridin-4-yl)phenyl]methoxy]pentyl)-2-(hydroxymethyl)piperidine-3,4,5-triol
Homo sapiens
pH and temperature not specified in the publication
0.000025
(2R,3R,4R,5S)-1-(5-[[4-(2H-1,3-benzodioxol-5-yl)phenyl]methoxy]pentyl)-2-(hydroxymethyl)piperidine-3,4,5-triol
Homo sapiens
pH and temperature not specified in the publication
0.00075
(2R,3R,4R,5S)-1-(5-[[4-(6-fluoropyridin-3-yl)phenyl]methoxy]pentyl)-2-(hydroxymethyl)piperidine-3,4,5-triol
Homo sapiens
pH and temperature not specified in the publication
0.00075
(2R,3R,4R,5S)-1-[5-(benzyloxy)pentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol
Homo sapiens
pH and temperature not specified in the publication
0.0005
(2R,3R,4R,5S)-1-[5-(cyclohexylmethoxy)pentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol
Homo sapiens
pH and temperature not specified in the publication
0.001
(2R,3R,4R,5S)-1-[5-([(3R,10S,13S,17R)-10,13-dimethyl-17-[(2S)-7-methyloctan-2-yl]-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy)pentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol
Homo sapiens
pH and temperature not specified in the publication
0.00006
(2R,3R,4R,5S)-1-[5-[(1R)-1-([1,1'-biphenyl]-4-yl)ethoxy]pentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol
Homo sapiens
pH and temperature not specified in the publication
0.00007
(2R,3R,4R,5S)-1-[5-[(1S)-1-([1,1'-biphenyl]-4-yl)ethoxy]pentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol
Homo sapiens
pH and temperature not specified in the publication
0.000075
(2R,3R,4R,5S)-1-[5-[(2'-fluoro[1,1'-biphenyl]-4-yl)methoxy]pentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol
Homo sapiens
pH and temperature not specified in the publication
0.000025
(2R,3R,4R,5S)-1-[5-[(2-fluoro[1,1'-biphenyl]-4-yl)methoxy]pentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol
Homo sapiens
pH and temperature not specified in the publication
0.000025
(2R,3R,4R,5S)-1-[5-[(3'-fluoro[1,1'-biphenyl]-4-yl)methoxy]pentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol
Homo sapiens
pH and temperature not specified in the publication
0.000025
(2R,3R,4R,5S)-1-[5-[(3-fluoro[1,1'-biphenyl]-4-yl)methoxy]pentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol
Homo sapiens
pH and temperature not specified in the publication
0.000025
(2R,3R,4R,5S)-1-[5-[(4'-chloro[1,1'-biphenyl]-4-yl)methoxy]pentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol
Homo sapiens
pH and temperature not specified in the publication
0.000025
(2R,3R,4R,5S)-1-[5-[(4'-fluoro[1,1'-biphenyl]-4-yl)methoxy]pentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol
Homo sapiens
pH and temperature not specified in the publication
0.000003
(2R,3R,4R,5S)-1-[5-[(4,8-dihydropyren-1-yl)methoxy]pentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol
Homo sapiens
pH and temperature not specified in the publication
0.000003
(2R,3R,4R,5S)-1-[5-[(5,8-dihydronaphthalen-2-yl)methoxy]pentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol
Homo sapiens
pH and temperature not specified in the publication
0.00005
(2R,3R,4R,5S)-1-[5-[([1,1'-biphenyl]-2-yl)methoxy]pentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol
Homo sapiens
pH and temperature not specified in the publication
0.000075
(2R,3R,4R,5S)-1-[5-[([1,1'-biphenyl]-3-yl)methoxy]pentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol
Homo sapiens
pH and temperature not specified in the publication
0.00125
(2R,3R,4R,5S)-1-[5-[([1,1'-biphenyl]-4-yl)methoxy]-2,2-difluoropentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol
Homo sapiens
pH and temperature not specified in the publication
0.00006
(2R,3R,4R,5S)-1-[5-[([1,1'-biphenyl]-4-yl)methoxy]-4,4-difluoropentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol
Homo sapiens
pH and temperature not specified in the publication
0.00005
(2R,3R,4R,5S)-1-[5-[([1,1'-biphenyl]-4-yl)methoxy]pentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol
Homo sapiens
pH and temperature not specified in the publication
0.0003
(2R,3R,4R,5S)-2-(hydroxymethyl)-1-((adamantylmethoxy)hexyl)piperidine-3,4,5-triol
Homo sapiens
pH and temperature not specified in the publication
0.0002
(2R,3R,4R,5S)-2-(hydroxymethyl)-1-(5-(adamantylmethoxy)pentyl)piperidine-3,4,5-triol
Homo sapiens
pH and temperature not specified in the publication
0.02
(2R,3R,4R,5S)-2-(hydroxymethyl)-1-(5-[[(2E,6E)-3,7,10-trimethylundeca-2,6,9-trien-1-yl]oxy]pentyl)piperidine-3,4,5-triol
Homo sapiens
above, pH and temperature not specified in the publication
0.000025
(2R,3R,4R,5S)-2-(hydroxymethyl)-1-(5-[[2-(trifluoromethyl)[1,1'-biphenyl]-4-yl]methoxy]pentyl)piperidine-3,4,5-triol
Homo sapiens
pH and temperature not specified in the publication
0.000025
(2R,3R,4R,5S)-2-(hydroxymethyl)-1-(5-[[3-(trifluoromethyl)[1,1'-biphenyl]-4-yl]methoxy]pentyl)piperidine-3,4,5-triol
Homo sapiens
pH and temperature not specified in the publication
0.00002
(2R,3R,4R,5S)-2-(hydroxymethyl)-1-(5-[[4'-(trifluoromethyl)[1,1'-biphenyl]-4-yl]methoxy]pentyl)piperidine-3,4,5-triol
Homo sapiens
pH and temperature not specified in the publication
0.000025
(2R,3R,4R,5S)-2-(hydroxymethyl)-1-(5-[[4-(2,3,4,5-tetrahydro-1,6-benzodioxocin-8-yl)phenyl]methoxy]pentyl)piperidine-3,4,5-triol
Homo sapiens
pH and temperature not specified in the publication
0.002
(2R,3R,4R,5S)-2-(hydroxymethyl)-1-(5-[[4-(pyridin-3-yl)phenyl]methoxy]pentyl)piperidine-3,4,5-triol
Homo sapiens
pH and temperature not specified in the publication
0.002
(2R,3R,4R,5S)-2-(hydroxymethyl)-1-(5-[[4-(pyridin-4-yl)phenyl]methoxy]pentyl)piperidine-3,4,5-triol
Homo sapiens
pH and temperature not specified in the publication
0.002
(2R,3R,4R,5S)-2-(hydroxymethyl)-1-(5-[[4-(pyrimidin-5-yl)phenyl]methoxy]pentyl)piperidine-3,4,5-triol
Homo sapiens
pH and temperature not specified in the publication
0.0003
(2R,3R,4R,5S)-2-(hydroxymethyl)-1-(6-(adamantylhexyl)hexyl)piperidine-3,4,5-triol
Homo sapiens
pH and temperature not specified in the publication
0.02
(2R,3R,4R,5S)-2-(hydroxymethyl)-1-(adamantylhept-6-en-1-yl)piperidine-3,4,5-triol
Homo sapiens
above, pH and temperature not specified in the publication
0.02
(2R,3R,4R,5S)-2-(hydroxymethyl)-1-(adamantylhexyl)piperidine-3,4,5-triol
Homo sapiens
above, pH and temperature not specified in the publication
0.00005
(2R,3R,4R,5S)-2-(hydroxymethyl)-1-[5-[(2'-methoxy[1,1'-biphenyl]-4-yl)methoxy]pentyl]piperidine-3,4,5-triol
Homo sapiens
pH and temperature not specified in the publication
0.000025
(2R,3R,4R,5S)-2-(hydroxymethyl)-1-[5-[(2'-methyl[1,1'-biphenyl]-4-yl)methoxy]pentyl]piperidine-3,4,5-triol
Homo sapiens
pH and temperature not specified in the publication
0.00015
(2R,3R,4R,5S)-2-(hydroxymethyl)-1-[5-[(3'-methoxy[1,1'-biphenyl]-4-yl)methoxy]pentyl]piperidine-3,4,5-triol
Homo sapiens
pH and temperature not specified in the publication
0.0001
(2R,3R,4R,5S)-2-(hydroxymethyl)-1-[5-[(3'-methyl[1,1'-biphenyl]-4-yl)methoxy]pentyl]piperidine-3,4,5-triol
Homo sapiens
pH and temperature not specified in the publication
0.000025
(2R,3R,4R,5S)-2-(hydroxymethyl)-1-[5-[(4'-methoxy[1,1'-biphenyl]-4-yl)methoxy]pentyl]piperidine-3,4,5-triol
Homo sapiens
pH and temperature not specified in the publication
0.0001
(2R,3R,4R,5S)-2-(hydroxymethyl)-1-[5-[(4'-methyl[1,1'-biphenyl]-4-yl)methoxy]pentyl]piperidine-3,4,5-triol
Homo sapiens
pH and temperature not specified in the publication
0.0002
(2R,3R,4R,5S)-2-(hydroxymethyl)-1-[5-[(5-phenylpyridin-2-yl)methoxy]pentyl]piperidine-3,4,5-triol
Homo sapiens
pH and temperature not specified in the publication
0.02
(2R,3R,4R,5S)-2-(hydroxymethyl)-1-[5-[(phenanthren-9-yl)methoxy]pentyl]piperidine-3,4,5-triol
Homo sapiens
above, pH and temperature not specified in the publication
0.0002
(2S,3R,4R,5S)-1-[5-(benzyloxy)pentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol
Homo sapiens
pH and temperature not specified in the publication
0.00007
(2S,3R,4R,5S)-1-[5-(cyclohexylmethoxy)pentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol
Homo sapiens
pH and temperature not specified in the publication
0.001
(2S,3R,4R,5S)-1-[5-([(3R,10S,13S,17R)-10,13-dimethyl-17-[(2S)-7-methyloctan-2-yl]-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy)pentyl]-2-(hydroxymethyl)piperidine-3,4,5-trio
Homo sapiens
pH and temperature not specified in the publication
0.00003
(2S,3R,4R,5S)-1-[5-[(1R)-1-([1,1'-biphenyl]-4-yl)ethoxy]pentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol
Homo sapiens
pH and temperature not specified in the publication
0.00004
(2S,3R,4R,5S)-1-[5-[(1S)-1-([1,1'-biphenyl]-4-yl)ethoxy]pentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol
Homo sapiens
pH and temperature not specified in the publication
0.0000025
(2S,3R,4R,5S)-1-[5-[(2-fluoro[1,1'-biphenyl]-4-yl)methoxy]pentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol
Homo sapiens
pH and temperature not specified in the publication
0.000005
(2S,3R,4R,5S)-1-[5-[(3-fluoro[1,1'-biphenyl]-4-yl)methoxy]pentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol
Homo sapiens
pH and temperature not specified in the publication
0.000003
(2S,3R,4R,5S)-1-[5-[(4,8-dihydropyren-1-yl)methoxy]pentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol
Homo sapiens
pH and temperature not specified in the publication
0.000003
(2S,3R,4R,5S)-1-[5-[(5,8-dihydronaphthalen-2-yl)methoxy]pentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol
Homo sapiens
pH and temperature not specified in the publication
0.000025
(2S,3R,4R,5S)-1-[5-[([1,1'-biphenyl]-2-yl)methoxy]pentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol
Homo sapiens
pH and temperature not specified in the publication
0.00007
(2S,3R,4R,5S)-1-[5-[([1,1'-biphenyl]-3-yl)methoxy]pentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol
Homo sapiens
pH and temperature not specified in the publication
0.00002
(2S,3R,4R,5S)-1-[5-[([1,1'-biphenyl]-4-yl)methoxy]-2,2-difluoropentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol
Homo sapiens
pH and temperature not specified in the publication
0.000015
(2S,3R,4R,5S)-1-[5-[([1,1'-biphenyl]-4-yl)methoxy]-4,4-difluoropentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol
Homo sapiens
pH and temperature not specified in the publication
0.000008
(2S,3R,4R,5S)-1-[5-[([1,1'-biphenyl]-4-yl)methoxy]pentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol
Homo sapiens
pH and temperature not specified in the publication
0.0001
(2S,3R,4R,5S)-2-(hydroxymethyl)-1-(5-(adamantylmethoxy)pentyl)piperidine-3,4,5-triol
Homo sapiens
pH and temperature not specified in the publication
0.0025
(2S,3R,4R,5S)-2-(hydroxymethyl)-1-(5-[[(2E,6E)-3,7,10-trimethylundeca-2,6,9-trien-1-yl]oxy]pentyl)piperidine-3,4,5-triol
Homo sapiens
pH and temperature not specified in the publication
0.000003
(2S,3R,4R,5S)-2-(hydroxymethyl)-1-(5-[[2-(trifluoromethyl)[1,1'-biphenyl]-4-yl]methoxy]pentyl)piperidine-3,4,5-triol
Homo sapiens
pH and temperature not specified in the publication
0.000003
(2S,3R,4R,5S)-2-(hydroxymethyl)-1-(5-[[3-(trifluoromethyl)[1,1'-biphenyl]-4-yl]methoxy]pentyl)piperidine-3,4,5-triol
Homo sapiens
pH and temperature not specified in the publication
0.00025
(2S,3R,4R,5S)-2-(hydroxymethyl)-1-(6-(adamantylmethoxy)hexyl)piperidine-3,4,5-triol
Homo sapiens
pH and temperature not specified in the publication
0.00008
(2S,3R,4R,5S)-2-(hydroxymethyl)-1-(6-adamantyloxyhexyl)piperidine-3,4,5-triol
Homo sapiens
pH and temperature not specified in the publication
0.02
(2S,3R,4R,5S)-2-(hydroxymethyl)-1-adamantylhexylpiperidine-3,4,5-triol
Homo sapiens
above, pH and temperature not specified in the publication
0.02
(2S,3R,4R,5S)-2-(hydroxymethyl)-1-[(6Z)-7-adamantylhept-6-en-1-yl]piperidine-3,4,5-triol
Homo sapiens
above, pH and temperature not specified in the publication
0.02
(2S,3R,4R,5S)-2-(hydroxymethyl)-1-[5-[(phenanthren-9-yl)methoxy]pentyl]piperidine-3,4,5-triol
Homo sapiens
above, pH and temperature not specified in the publication
0.00015
4'-[([5-[(2R,3R,4R,5S)-3,4,5-trihydroxy-2-(hydroxymethyl)piperidin-1-yl]pentyl]oxy)methyl][1,1'-biphenyl]-2-carbonitrile
Homo sapiens
pH and temperature not specified in the publication
0.00005
4'-[([5-[(2R,3R,4R,5S)-3,4,5-trihydroxy-2-(hydroxymethyl)piperidin-1-yl]pentyl]oxy)methyl][1,1'-biphenyl]-3-carbonitrile
Homo sapiens
pH and temperature not specified in the publication
0.00015
4'-[([5-[(2R,3R,4R,5S)-3,4,5-trihydroxy-2-(hydroxymethyl)piperidin-1-yl]pentyl]oxy)methyl][1,1'-biphenyl]-4-carbonitrile
Homo sapiens
pH and temperature not specified in the publication
0.0002
N-adamantanemethoxypentyldeoxynojirimycin
Homo sapiens
pH 5.2, 37°C
0.001
N-adamantyl-6-[(2R,3R,4R,5S)-3,4,5-trihydroxy-2-(hydroxymethyl)piperidin-1-yl]hexanamide
Homo sapiens
pH and temperature not specified in the publication
0.0004
N-adamantyl-6-[(2S,3R,4R,5S)-3,4,5-trihydroxy-2-(hydroxymethyl)piperidin-1-yl]hexanamide
Homo sapiens
pH and temperature not specified in the publication
0.0008
N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-1-hydroxy-3-(morpholin-4-yl)propan-2-yl]-2-(4-methoxyphenoxy)acetamide
Homo sapiens
pH 5.2, 37°C
0.00075
N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-1-hydroxy-3-(morpholin-4-yl)propan-2-yl]-5-(adamantylmethoxy)pentanamide
Homo sapiens
pH 5.2, 37°C
0.0008
N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-1-hydroxy-3-(morpholin-4-yl)propan-2-yl]nonanamide
Homo sapiens
pH 5.2, 37°C
0.0008
N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-1-hydroxy-3-(piperidin-1-yl)propan-2-yl]-2-(4-methoxyphenoxy)acetamide
Homo sapiens
pH 5.2, 37°C
0.0015
N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-1-hydroxy-3-(piperidin-1-yl)propan-2-yl]-5-(adamantylmethoxy)pentanamide
Homo sapiens
pH 5.2, 37°C
0.001
N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-1-hydroxy-3-(piperidin-1-yl)propan-2-yl]nonanamide
Homo sapiens
pH 5.2, 37°C
0.00005
N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-1-hydroxy-3-(pyrrolidin-1-yl)propan-2-yl]-2-(4-methoxyphenoxy)acetamide
Homo sapiens
pH 5.2, 37°C
0.0001
N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-1-hydroxy-3-(pyrrolidin-1-yl)propan-2-yl]-5(adamantylmethoxy)pentanamide
Homo sapiens
pH 5.2, 37°C
0.0001
N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-1-hydroxy-3-(pyrrolidin-1-yl)propan-2-yl]nonanamide
Homo sapiens
pH 5.2, 37°C
0.01
N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-1-hydroxy-3-[(2R,3R,4R,5S)-3,4,5-trihydroxy-2-(hydroxymethyl)piperidin-1-yl]propan-2-yl]-2-(4-methoxyphenoxy)acetamide
Homo sapiens
pH 5.2, 37°C
0.01
N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-1-hydroxy-3-[(2R,3R,4R,5S)-3,4,5-trihydroxy-2-(hydroxymethyl)piperidin-1-yl]propan-2-yl]-5-(adamantylmethoxy)pentanamide
Homo sapiens
pH 5.2, 37°C
0.01
N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-1-hydroxy-3-[(2R,3R,4R,5S)-3,4,5-trihydroxy-2-(hydroxymethyl)piperidin-1-yl]propan-2-yl]nonanamide
Homo sapiens
pH 5.2, 37°C
0.01
N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-1-hydroxy-3-[(2R,3S,4R,5S)-3,4,5-trihydroxy-2-(hydroxymethyl)piperidin-1-yl]propan-2-yl]-2-(4-methoxyphenoxy)acetamide
Homo sapiens
pH 5.2, 37°C
0.01
N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-1-hydroxy-3-[(2R,3S,4R,5S)-3,4,5-trihydroxy-2-(hydroxymethyl)piperidin-1-yl]propan-2-yl]-5-(adamantylmethoxy)pentanamide
Homo sapiens
pH 5.2, 37°C
0.01
N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-1-hydroxy-3-[(2R,3S,4R,5S)-3,4,5-trihydroxy-2-(hydroxymethyl)piperidin-1-yl]propan-2-yl]nonanamide
Homo sapiens
pH 5.2, 37°C
0.01
N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-1-hydroxy-3-[(2S,3R,4R,5S)-3,4,5-trihydroxy-2-(hydroxymethyl)piperidin-1-yl]propan-2-yl]-2-(4-methoxyphenoxy)acetamide
Homo sapiens
pH 5.2, 37°C
0.01
N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-1-hydroxy-3-[(2S,3R,4R,5S)-3,4,5-trihydroxy-2-(hydroxymethyl)piperidin-1-yl]propan-2-yl]-5-(adamantylmethoxy)pentanamide
Homo sapiens
pH 5.2, 37°C
0.01
N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-1-hydroxy-3-[(2S,3R,4R,5S)-3,4,5-trihydroxy-2-(hydroxymethyl)piperidin-1-yl]propan-2-yl]nonanamide
Homo sapiens
pH 5.2, 37°C
0.01
N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-1-hydroxy-3-[(2S,3S,4R,5S)-3,4,5-trihydroxy-2-(hydroxymethyl)piperidin-1-yl]propan-2-yl]-2-(4-methoxyphenoxy)acetamide
Homo sapiens
pH 5.2, 37°C
0.01
N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-1-hydroxy-3-[(2S,3S,4R,5S)-3,4,5-trihydroxy-2-(hydroxymethyl)piperidin-1-yl]propan-2-yl]-5-(adamantylmethoxy)pentanamide
Homo sapiens
pH 5.2, 37°C
0.01
N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-1-hydroxy-3-[(2S,3S,4R,5S)-3,4,5-trihydroxy-2-(hydroxymethyl)piperidin-1-yl]propan-2-yl]nonanamide
Homo sapiens
pH 5.2, 37°C
0.01
N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-3-[(2R,3R,4R)-3,4-dihydroxy-2-(hydroxymethyl)pyrrolidin-1-yl]-1-hydroxypropan-2-yl]-2-(4-methoxyphenoxy)acetamide
Homo sapiens
pH 5.2, 37°C
0.01
N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-3-[(2R,3R,4R)-3,4-dihydroxy-2-(hydroxymethyl)pyrrolidin-1-yl]-1-hydroxypropan-2-yl]-5-(adamantylmethoxy)pentanamide
Homo sapiens
pH 5.2, 37°C
0.01
N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-3-[(2R,3R,4R)-3,4-dihydroxy-2-(hydroxymethyl)pyrrolidin-1-yl]-1-hydroxypropan-2-yl]nonanamide
Homo sapiens
pH 5.2, 37°C
0.01
N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-3-[(2R,3R,4S)-3,4-dihydroxy-2-(hydroxymethyl)pyrrolidin-1-yl]-1-hydroxypropan-2-yl]-2-(4-methoxyphenoxy)acetamide
Homo sapiens
pH 5.2, 37°C
0.01
N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-3-[(2R,3R,4S)-3,4-dihydroxy-2-(hydroxymethyl)pyrrolidin-1-yl]-1-hydroxypropan-2-yl]-5-(adamantylmethoxy)pentanamide
Homo sapiens
pH 5.2, 37°C
0.01
N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-3-[(2R,3R,4S)-3,4-dihydroxy-2-(hydroxymethyl)pyrrolidin-1-yl]-1-hydroxypropan-2-yl]nonanamide
Homo sapiens
pH 5.2, 37°C
0.01
N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-3-[(2R,3S,4R)-3,4-dihydroxy-2-(hydroxymethyl)pyrrolidin-1-yl]-1-hydroxypropan-2-yl]-2-(4-methoxyphenoxy)acetamide
Homo sapiens
pH 5.2, 37°C
0.01
N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-3-[(2R,3S,4R)-3,4-dihydroxy-2-(hydroxymethyl)pyrrolidin-1-yl]-1-hydroxypropan-2-yl]-5-(adamantylmethoxy)pentanamide
Homo sapiens
pH 5.2, 37°C
0.01
N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-3-[(2R,3S,4R)-3,4-dihydroxy-2-(hydroxymethyl)pyrrolidin-1-yl]-1-hydroxypropan-2-yl]nonanamide
Homo sapiens
pH 5.2, 37°C
0.01
N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-3-[(2R,3S,4S)-3,4-dihydroxy-2-(hydroxymethyl)pyrrolidin-1-yl]-1-hydroxypropan-2-yl]-2-(4-methoxyphenoxy)acetamide
Homo sapiens
pH 5.2, 37°C
0.01
N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-3-[(2R,3S,4S)-3,4-dihydroxy-2-(hydroxymethyl)pyrrolidin-1-yl]-1-hydroxypropan-2-yl]-5-(adamantylmethoxy)pentanamide
Homo sapiens
pH 5.2, 37°C
0.01
N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-3-[(2R,3S,4S)-3,4-dihydroxy-2-(hydroxymethyl)pyrrolidin-1-yl]-1-hydroxypropan-2-yl]nonanamide
Homo sapiens
pH 5.2, 37°C
0.01
N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-3-[(2S,3R,4S)-3,4-dihydroxy-2-(hydroxymethyl)pyrrolidin-1-yl]-1-hydroxypropan-2-yl]-2-(4-methoxyphenoxy)acetamide
Homo sapiens
pH 5.2, 37°C
0.01
N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-3-[(2S,3R,4S)-3,4-dihydroxy-2-(hydroxymethyl)pyrrolidin-1-yl]-1-hydroxypropan-2-yl]-5-(adamantylmethoxy)pentanamide
Homo sapiens
pH 5.2, 37°C
0.01
N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-3-[(2S,3R,4S)-3,4-dihydroxy-2-(hydroxymethyl)pyrrolidin-1-yl]-1-hydroxypropan-2-yl]nonanamide
Homo sapiens
pH 5.2, 37°C
0.01
N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-3-[(2S,3S,4S)-3,4-dihydroxy-2-(hydroxymethyl)pyrrolidin-1-yl]-1-hydroxypropan-2-yl]-2-(4-methoxyphenoxy)acetamide
Homo sapiens
pH 5.2, 37°C
0.01
N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-3-[(2S,3S,4S)-3,4-dihydroxy-2-(hydroxymethyl)pyrrolidin-1-yl]-1-hydroxypropan-2-yl]-5-(adamantylmethoxy)pentanamide
Homo sapiens
pH 5.2, 37°C
0.01
N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-3-[(2S,3S,4S)-3,4-dihydroxy-2-(hydroxymethyl)pyrrolidin-1-yl]-1-hydroxypropan-2-yl]nonanamide
Homo sapiens
pH 5.2, 37°C
0.174
(1R)-1-C-octyl-N-octyl-1,5-dideoxy-1,5-imino-Dglucitol
Homo sapiens
-
-
0.609
(1R)-N-butyl-1-C-butyl-1,5-dideoxy-1,5-imino-D-glucitol
Homo sapiens
-
-
0.009
(1S)-1-C-[5-(adamantan-1-yl-methoxy)-pentyl]-1-deoxynojirimycin
Homo sapiens
-
-
0.025
(1S)-N-butyl-1-C-[5-(adamantan-1-yl-methoxy)-pentyl]-1-deoxynojirimycin
Homo sapiens
-
-
0.164
N-octyl-2-O-octyl-1,5-dideoxy-1,5-imino-D-glucitol
Homo sapiens
-
-
0.134
N-octyl-4-O-octyl-1,5-dideoxy-1,5-imino-D-glucitol
Homo sapiens
-
-
0.0002
N-[5-(adamantan-1-yl-methoxy)-pentyl]-1-deoxynojirimycin
Homo sapiens
-
-
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.00017
-
recombinant enzyme in cell extract of cell line KB-3-1
0.00021
-
recombinant enzyme in cell extract of cell line KB-A1
0.00024
-
recombinant enzyme in cell extract of cell line KB-V.1
0.00025
-
recombinant enzyme in cell extract of cell line KB-A.05
0.00036
-
recombinant enzyme in cell extract of cell line KB-V1
additional information
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7
-
assay at
7.8
-
assay at
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
30
-
assay at
37
-
assay at
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
high enzyme expression level and content
Manually annotated by BRENDA team
high enzyme expression level and content
Manually annotated by BRENDA team
vinorelbine-resistant, high expression of enzyme GCS in lung cancer cells resistant to vinorelbine-induced apoptosis
Manually annotated by BRENDA team
-
of leukaemic patients before chemotherapy
Manually annotated by BRENDA team
-
GCS expression is significantly decreased in cortex of Alzheimer disease patients
Manually annotated by BRENDA team
-
it is shown that overexpression of the GCS gene is associated with multidrug resistance of leukemia cells
Manually annotated by BRENDA team
-
peripheral blood cell of leukaemic patients before chemotherapy
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
metabolism
glucosylceramide synthase catalyzes the first committed step in the biosynthesis of glucosylceramide-related glycosphingolipids, pathway overview
physiological function
malfunction
metabolism
-
key enzyme for the synthesis of glycosphingolipids which plays a role in physiology and diseases for instance in drug-resistant cancers
additional information
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION?
CEGT_HUMAN
394
3
44854
Swiss-Prot
Secretory Pathway (Reliability: 1)
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
448530
38000
-
x * 38000, SDS-PAGE
additional information
SUBUNIT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
-
antisense expression inhibits enzyme activity
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
cloning and transient expression in GM-95 cell line, mutant cell line containing no enzyme activity, derived from melanoma mutant cell line B16, DNA sequence determination and analysis
expression in MCF-7 cell
functional expression in Escherichia coli BL21(DE3)
expressed in different drug-resistant human cancer cell lines
-
expressed in PC12 cells
-
expression in an enzyme-deficient strain of Pichia pastoris
-
expression of enzyme gene in antisense orientation, two-hybrid system: coexpression with the reticulon RTN family, interaction especially with RTN-1C
-
gene GluT-1 cloned from a human melanoma genetic library, transient overexpression in HL-60 and HL-60/ADR cells, induced resistance to DOX in HL-60 cells
-
overexpression in cancer cell lines selected for resistance to natural product chemotherapy, i.e. cell lines KB-3-1, KB-V.01, KB-V.1, KB-V1, KB-A.05, MCF-7, and MCF-7-AdrR, cell lines show different recombinant enzyme activity, which is higherin cells resistant to natural product anticancer agents, e.g. vinblastine and adriamycin, overview
-
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
Vinca alkaloid vinorelbine induces the enzyme in vinorelbine-resitant cells
glucosylceramide synthase expression is enhanced in breast cancer stem cells but not in normal mammary epithelial stem cells
-
in the absence of p53, mitomycin C treatment elicits a down-regulation of the enzyme
-
the mixed-backbone oligonucleotide MBO-asGCS decreases mRNA levels in human tumor cell lines by 65%
-
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
drug development
the enzyme is an attractive target for drug development both in relation to lysosomal storage disorders (in particular Gaucher disease) and type2 diabetes
medicine
medicine
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Basu, S.; Kaufman, B.; Roseman, S.
Enzymatic synthesis of glucocerebroside by a glucosyltransferase from embryonic chicken brain
J. Biol. Chem.
248
1388-1394
1973
Cavia porcellus, Gallus gallus, Ovis aries, Homo sapiens, Rattus norvegicus, Sus scrofa
Manually annotated by BRENDA team
Ichikawa, S.; Sakiyama, H.; Suzuki, G.; Hidari, K.I.P.J.; Hirabayashi, Y.
Expression cloning of a cDNA for human ceramide glucosyltransferase that catalyzes the first glycosylation step of glycosphingolipid synthesis
Proc. Natl. Acad. Sci. USA
93
4638-4643
1996
Homo sapiens (Q16739), Homo sapiens
Manually annotated by BRENDA team
Ichikawa, S.; Hirabayashi, Y.
Glucosylceramide synthase and glycosphingolipid synthesis
Trends Cell Biol.
8
198-202
1998
Caenorhabditis elegans, Mus musculus, Rattus norvegicus, Homo sapiens (Q16739)
Manually annotated by BRENDA team
Itoh, M.; Kitano, T.; Watanabe, M.; Kondo, T.; Yabu, T.; Taguchi, Y.; Iwai, K.; Tashima, M.; Uchiyama, T.; Okazaki, T.
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
Clin. Cancer Res.
9
415-423
2003
Homo sapiens
Manually annotated by BRENDA team
Marks, D.L.; Wu, K.; Paul, P.; Kamisaka, Y.; Watanabe, R.; Pagano, R.E.
Oligomerization and topology of the Golgi membrane protein glucosylceramide synthase
J. Biol. Chem.
274
451-456
1999
Homo sapiens, Rattus norvegicus
Manually annotated by BRENDA team
Wu, K.; Marks, D.L.; Watanabe, R.; Paul, P.; Rajan, N.; Pagano, R.E.
Histidine-193 of rat glucosylceramide synthase resides in a UDP-glucose-and inhibitor (D-threo-1-phenyl-2-decanoylamino-3-morpholinopropan-1-ol)-binding region: a biochemical and mutational study
Biochem. J.
341
395-400
1999
Homo sapiens (Q16739), Rattus norvegicus (Q9R0E0)
-
Manually annotated by BRENDA team
Shayman, J.A.; Abe, A.
Glucosylceramide synthase: assay and properties
Methods Enzymol.
311
42-49
2000
Canis lupus familiaris, Homo sapiens, Homo sapiens (Q16739)
Manually annotated by BRENDA team
Marks, D.L.; Paul, P.; Kamisaka, Y.; Pagano, R.E.
Methods for studying glucosylceramide synthase
Methods Enzymol.
311
50-59
2000
Gallus gallus, Homo sapiens, Homo sapiens (Q16739), Mus musculus, Rattus norvegicus, Rattus norvegicus (Q9R0E0), Rattus norvegicus Sprague-Dawley, Sus scrofa
Manually annotated by BRENDA team
Hillig, I.; Warnecke, D.; Heinz, E.
An inhibitor of glucosylceramide synthase inhibits the human enzyme, but not enzymes from other organisms
Biosci. Biotechnol. Biochem.
69
1782-1785
2005
Homo sapiens
Manually annotated by BRENDA team
Di Sano, F.; Fazi, B.; Citro, G.; Lovat, P.E.; Cesareni, G.; Piacentini, M.
Glucosylceramide synthase and its functional interaction with RTN-1C regulate chemotherapeutic-induced apoptosis in neuroepithelioma cells
Cancer Res.
63
3860-3865
2003
Homo sapiens
Manually annotated by BRENDA team
Gouaze, V.; Yu, J.Y.; Bleicher, R.J.; Han, T.Y.; Liu, Y.Y.; Wang, H.; Gottesman, M.M.; Bitterman, A.; Giuliano, A.E.; Cabot, M.C.
Overexpression of glucosylceramide synthase and P-glycoprotein in cancer cells selected for resistance to natural product chemotherapy
Mol. Cancer Ther.
3
633-639
2004
Homo sapiens
Manually annotated by BRENDA team
Boucheron, C.; Desvergnes, V.; Compain, P.; Martin, O.R.; Lavi, A.; Mackeen, M.; Wormald, M.; Dwek, R.; Butters, T.D.
Design and synthesis of imino-sugar-based inhibitors of glucosylceramide synthase: the search for new therapeutic agents against Gaucher disease
Tetrahedron
16
1747-1756
2005
Homo sapiens
-
Manually annotated by BRENDA team
Marks, N.; Berg, M.J.; Saito, M.; Saito, M.
Glucosylceramide synthase decrease in frontal cortex of Alzheimer brain correlates with abnormal increase in endogenous ceramides: consequences to morphology and viability on enzyme suppression in cultured primary neurons
Brain Res.
1191
136-147
2008
Homo sapiens, Rattus norvegicus
Manually annotated by BRENDA team
Li, H.; Liu, T.; Zhang, Y.; Favre, S.; Bello, C.; Vogel, P.; Butters, T.D.; Oikonomakos, N.G.; Marrot, J.; Bleriot, Y.
New synthetic seven-membered 1-azasugars displaying potent inhibition towards glycosidases and glucosylceramide transferase
ChemBioChem
9
253-260
2008
Homo sapiens
Manually annotated by BRENDA team
Dbaibo, G.S.; Kfoury, Y.; Darwiche, N.; Panjarian, S.; Kozhaya, L.; Nasr, R.; Abdallah, M.; Hermine, O.; El-Sabban, M.; de The, H.; Bazarbachi, A.
Arsenic trioxide induces accumulation of cytotoxic levels of ceramide in acute promyelocytic leukemia and adult T-cell leukemia/lymphoma cells through de novo ceramide synthesis and inhibition of glucosylceramide synthase activity
Haematologica
92
753-762
2007
Homo sapiens
Manually annotated by BRENDA team
Xie, P.; Shen, Y.F.; Shi, Y.P.; Ge, S.M.; Gu, Z.H.; Wang, J.; Mu, H.J.; Zhang, B.; Qiao, W.Z.; Xie, K.M.
Overexpression of glucosylceramide synthase in associated with multidrug resistance of leukemia cells
Leuk. Res.
32
475-480
2008
Homo sapiens
Manually annotated by BRENDA team
Wennekes, T.; Lang, B.; Leeman, M.; van der Marel, G.A.; Smits, E.; Weber, M.; van Wiltenburg, J.; Wolberg, M.; Aerts, J.M.; Overkleeft, H.S.
Large-Scale Synthesis of the Glucosylceramide Synthase Inhibitor N-[5-(Adamantan-1-yl-methoxy)-pentyl]-1-deoxynojirimycin
Org. Process Res. Dev.
12
414-423
2008
Homo sapiens
-
Manually annotated by BRENDA team
Crespo, P.M.; Silvestre, D.C.; Gil, G.A.; Maccioni, H.J.; Daniotti, J.L.; Caputto, B.L.
c-Fos activates glucosylceramide synthase and glycolipid synthesis in PC12 cells
J. Biol. Chem.
283
31163-31171
2008
Homo sapiens
Manually annotated by BRENDA team
Ruckhaeberle, E.; Karn, T.; Hanker, L.; Gaetje, R.; Metzler, D.; Holtrich, U.; Kaufmann, M.; Rody, A.
Prognostic relevance of glucosylceramide synthase (GCS) expression in breast cancer
J. Cancer Res. Clin. Oncol.
135
81-90
2009
Homo sapiens
Manually annotated by BRENDA team
Gupta, V.; Patwardhan, G.A.; Zhang, Q.J.; Cabot, M.C.; Jazwinski, S.M.; Liu, Y.Y.
Direct quantitative determination of ceramide glycosylation in vivo: a new approach to evaluate cellular enzyme activity of glucosylceramide synthase (GlcT-1)
J. Lipid Res.
51
866-874
2010
Homo sapiens
Manually annotated by BRENDA team
Patwardhan, G.; Zhang, Q.; Yin, D.; Gupta, V.; Bao, J.; Senkal, C.; Ogretmen, B.; Cabot, M.; Shah, G.; Sylvester, P.; Jazwinski, S.; Liu, Y.
A new mixed-backbone oligonucleotide against glucosylceramide synthase sensitizes multidrug-resistant tumors to apoptosis
PLoS ONE
4
e6938
2009
Homo sapiens, Mus musculus
Manually annotated by BRENDA team
Haynes, T.A.; Filippov, V.; Filippova, M.; Yang, J.; Zhang, K.; Duerksen-Hughes, P.J.
DNA damage induces down-regulation of UDP-glucose ceramide glucosyltransferase, increases ceramide levels and triggers apoptosis in p53-deficient cancer cells
Biochim. Biophys. Acta
1821
943-953
2012
Homo sapiens
Manually annotated by BRENDA team
Gupta, V.; Bhinge, K.N.; Hosain, S.B.; Xiong, K.; Gu, X.; Shi, R.; Ho, M.Y.; Khoo, K.H.; Li, S.C.; Li, Y.T.; Ambudkar, S.V.; Jazwinski, S.M.; Liu, Y.Y.
Ceramide glycosylation by glucosylceramide synthase selectively maintains the properties of breast cancer stem cells
J. Biol. Chem.
287
37195-37205
2012
Homo sapiens
Manually annotated by BRENDA team
Ghisaidoobe, A.T.; van den Berg, R.J.; Butt, S.S.; Strijland, A.; Donker-Koopman, W.E.; Scheij, S.; van den Nieuwendijk, A.M.; Koomen, G.J.; van Loevezijn, A.; Leemhuis, M.; Wennekes, T.; van der Stelt, M.; van der Marel, G.A.; van Boeckel, C.A.; Aerts, J.M.; Overkleeft, H.S.
Identification and development of biphenyl substituted iminosugars as improved dual glucosylceramide synthase/neutral glucosylceramidase inhibitors
J. Med. Chem.
57
9096-9104
2014
Homo sapiens (Q16739)
Manually annotated by BRENDA team
Niino, S.; Nakamura, Y.; Hirabayashi, Y.; Nagano-Ito, M.; Ichikawa, S.
A small molecule inhibitor of Bcl-2, HA14-1, also inhibits ceramide glucosyltransferase
Biochem. Biophys. Res. Commun.
433
170-174
2013
Homo sapiens (Q16739)
Manually annotated by BRENDA team
van den Berg, R.J.; van Rijssel, E.R.; Ferraz, M.J.; Houben, J.; Strijland, A.; Donker-Koopman, W.E.; Wennekes, T.; Bonger, K.M.; Ghisaidoobe, A.B.; Hoogendoorn, S.; van der Marel, G.A.; Codee, J.D.; Overkleeft, H.S.; Aerts, J.M.
Synthesis and evaluation of hybrid structures composed of two glucosylceramide synthase inhibitors
ChemMedChem
10
2042-2062
2015
Homo sapiens (Q16739)
Manually annotated by BRENDA team
Alam, S.; Fedier, A.; Kohler, R.S.; Jacob, F.
Glucosylceramide synthase inhibitors differentially affect expression of glycosphingolipids
Glycobiology
25
351-356
2015
Homo sapiens (Q16739)
Manually annotated by BRENDA team
Chiu, W.H.; Su, W.C.; Li, C.L.; Chen, C.L.; Lin, C.F.
An increase in glucosylceramide synthase induces Bcl-xL-mediated cell survival in vinorelbine-resistant lung adenocarcinoma cells
Oncotarget
6
20513-20524
2015
Homo sapiens (Q16739)
Manually annotated by BRENDA team
Wegner, M.S.; Schoemel, N.; Gruber, L.; Oertel, S.B.; Kjellberg, M.A.; Mattjus, P.; Kurz, J.; Trautmann, S.; Peng, B.; Wegner, M.; Kaulich, M.; Ahrends, R.; Geisslinger, G.; Groesch, S.
UDP-glucose ceramide glucosyltransferase activates AKT, promoted proliferation, and doxorubicin resistance in breast cancer cells
Cell. Mol. Life Sci.
75
3393-3410
2018
Homo sapiens (Q16739)
Manually annotated by BRENDA team