Information on EC 2.4.1.80 - ceramide glucosyltransferase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
2.4.1.80
-
RECOMMENDED NAME
GeneOntology No.
ceramide glucosyltransferase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
UDP-glucose + an N-acylsphingosine = UDP + a D-glucosyl-N-acylsphingosine
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
hexosyl group transfer
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
sphingolipid biosynthesis (plants)
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-
Sphingolipid metabolism
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-
Metabolic pathways
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-
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
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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-
-
Manually annotated by BRENDA team
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-
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Manually annotated by BRENDA team
COS7 cells
-
-
Manually annotated by BRENDA team
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Q58FH5
SwissProt
Manually annotated by BRENDA team
zebrafish
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-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
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-
-
Manually annotated by BRENDA team
radish
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-
Manually annotated by BRENDA team
Sprague-Dawley
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-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
metabolism
physiological function
additional information
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
CDP-glucose + N-acylsphingosine
CDP + D-glucosyl-N-acylsphingosine
show the reaction diagram
-
i.e. ceramide
i.e. glucosylceramide
?
TDP-glucose + N-acylsphingosine
TDP + D-glucosyl-N-acylsphingosine
show the reaction diagram
-
i.e. ceramide
i.e. glucosylceramide
?
UDP + 6-[N-methyl-N-(7-nitrobenz-2-oxa-1,3-diazol-4-yl)aminododecanoyl]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 + 6-([(N-7-nitrobenz-2-oxa-1,3-diazol-4-yl)amino]caproyl)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 + an N-acylsphingosine
UDP + a D-glucosyl-N-acylsphingosine
show the reaction diagram
-
-
-
-
?
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 + D-glucosyl-ceramide
show the reaction diagram
-
-
-
-
?
UDP-glucose + ceramide
UDP + glucosylceramide
show the reaction diagram
UDP-glucose + decasphingosine
UDP + D-glucosyl-decasphingosine
show the reaction diagram
-
-
-
?
UDP-glucose + dihydroceramide
UDP + D-glucosyl-dihydroceramide
show the reaction diagram
-
mono-, tri-, and tetrahexosylceramides, the parasite enzyme is only active on the saturated substrate
product analysis
-
?
UDP-glucose + dihydrosphingosine
UDP + D-glucosyl-dihydrosphingosine
show the reaction diagram
UDP-glucose + lauroyl amide
UDP + D-glucosyllauroyl amide
show the reaction diagram
-
-
-
-
?
UDP-glucose + N-(epsilon-7-nitrobenz-2-oxa-1,3-diazol-4-yl-aminocaproyl)-D-erythro-sphingosine
?
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
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-
-
-
?
UDP-glucose + N-acylsphinganine
UDP + D-glucosyl-N-acylsphingosine
show the reaction diagram
-
stereospecific and dependent on nature and chain length of N-acylsphinganine substrate
-
?
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
UDP-glucose + N-[7-(4-nitrobenzo-2-oxa-1,3-diazole)]-6-aminocaproyl-D-erythro-sphingosine
UDP + D-glucosyl-N-[7-(4-nitrobenzo-2-oxa-1,3-diazole)]-6-aminocaproyl-D-erythro-sphingosine
show the reaction diagram
UDP-glucose + sphingosine
UDP + D-glucosyl-sphingosine
show the reaction diagram
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-
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?
additional information
?
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
UDP-glucose + an N-acylsphingosine
UDP + a D-glucosyl-N-acylsphingosine
show the reaction diagram
-
-
-
-
?
UDP-glucose + ceramide
UDP + glucosylceramide
show the reaction diagram
UDP-glucose + N-acylsphingosine
UDP + D-glucosyl-N-acylsphingosine
show the reaction diagram
additional information
?
-
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Ba2+
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activates
additional information
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(+/-)-threo-1-phenyl-2-decanoylamino-3-morpholino-1-propanol hydrochloride
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-
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(1R)-1-C-octyl-N-octyl-1,5-dideoxy-1,5-imino-D-glucitol
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(1R)-N-butyl-1-C-butyl-1,5-dideoxy-1,5-imino-D-glucitol
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-
(1S)-1-C-[5-(adamantan-1-yl-methoxy)-pentyl]-1-deoxynojirimycin
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-
(1S)-N-butyl-1-C-[5-(adamantan-1-yl-methoxy)-pentyl]-1-deoxynojirimycin
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-
(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
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-
(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
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-
(2R,3R,4R,5S)-1-(5-[[4-(2-fluoropyridin-4-yl)phenyl]methoxy]pentyl)-2-(hydroxymethyl)piperidine-3,4,5-triol
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-
(2R,3R,4R,5S)-1-(5-[[4-(2H-1,3-benzodioxol-5-yl)phenyl]methoxy]pentyl)-2-(hydroxymethyl)piperidine-3,4,5-triol
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-
(2R,3R,4R,5S)-1-(5-[[4-(6-fluoropyridin-3-yl)phenyl]methoxy]pentyl)-2-(hydroxymethyl)piperidine-3,4,5-triol
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(2R,3R,4R,5S)-1-butyl-2-(hydroxymethyl)piperidine-3,4,5-triol
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i.e. miglustat or Zavesca
(2R,3R,4R,5S)-1-[5-(benzyloxy)pentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol
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(2R,3R,4R,5S)-1-[5-(cyclohexylmethoxy)pentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol
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(2R,3R,4R,5S)-1-[5-(hexyloxy)pentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol
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(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
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-
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(2R,3R,4R,5S)-1-[5-[(1R)-1-([1,1'-biphenyl]-4-yl)ethoxy]pentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol
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-
(2R,3R,4R,5S)-1-[5-[(1S)-1-([1,1'-biphenyl]-4-yl)ethoxy]pentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol
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(2R,3R,4R,5S)-1-[5-[(2'-fluoro[1,1'-biphenyl]-4-yl)methoxy]pentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol
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-
(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
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(2R,3R,4R,5S)-1-[5-[(4'-chloro[1,1'-biphenyl]-4-yl)methoxy]pentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol
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-
(2R,3R,4R,5S)-1-[5-[(4'-fluoro[1,1'-biphenyl]-4-yl)methoxy]pentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol
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-
(2R,3R,4R,5S)-1-[5-[(4,8-dihydropyren-1-yl)methoxy]pentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol
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-
(2R,3R,4R,5S)-1-[5-[(5,8-dihydronaphthalen-2-yl)methoxy]pentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol
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-
(2R,3R,4R,5S)-1-[5-[([1,1'-biphenyl]-2-yl)methoxy]pentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol
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(2R,3R,4R,5S)-1-[5-[([1,1'-biphenyl]-3-yl)methoxy]pentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol
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(2R,3R,4R,5S)-1-[5-[([1,1'-biphenyl]-4-yl)methoxy]-2,2-difluoropentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol
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(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
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-
(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
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-
(2R,3R,4R,5S)-2-(hydroxymethyl)-1-(5-[[2-(trifluoromethyl)[1,1'-biphenyl]-4-yl]methoxy]pentyl)piperidine-3,4,5-triol
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-
(2R,3R,4R,5S)-2-(hydroxymethyl)-1-(5-[[3-(trifluoromethyl)[1,1'-biphenyl]-4-yl]methoxy]pentyl)piperidine-3,4,5-triol
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-
(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
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-
(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
-
-
(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)-2-(hydroxymethyl)pyrrolidin-3-ol
-
0.05 mM, about 15% inhibition
(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
-
-
(2S,3R,4S)-2-(hydroxymethyl)-4-octylpyrrolidin-3-ol
-
0.01 mM, about 70% inhibition
(2S,3R,4S)-4-butyl-2-(hydroxymethyl)pyrrolidin-3-ol
-
0.05 mM, about 30% inhibition
(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
-
-
2-decanoylamido-3-morpholinopropiophenone
-
45% inhibition at 0.3 mM
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
-
-
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
CHAPS
-
i.e. 3-[(3-cholamidopropyl)dimethylammonio]-1propanesulfonate
D,L-threo-1-phenyl-2-(decanoylamino)-3-morpholino-1-propanol-HCl
-
accumulation of ceramide in the cells, higher amount in Z65 mutant than in strain K1
D,L-threo-1-phenyl-2-palmitoylamino-3-morpholino-1-propanol
-
enzyme inhibition in vitro and in vivo, in the latter case the compound also inhibits growth of the parasite
D-threo-1-phenyl-2-(decanoylamino)-3-morpholino-1-propanol-HCl
D-threo-2-palmitoylamino-3-pyrrolidino-1-propanol
Detergents
-
e.g. 0.5% Triton X-100 or 0.5% sodium deoxycholate; inhibition of enzyme due to permeabilization of microsomal membrane
diethyl dicarbonate
-
i.e. DEPC; reversible by hydroxylamine, UDP-glucose protects, inhibitor acts on histidine residues, including His193, within or near UDP-glucose binding site
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-hexadecanoyl-amino-3-pyrrolidino-1-propanol
-
i.e. most active PDMP-type congener, specific and reversible, in vivo and in vitro
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
doxorubicin
-
i.e. DOX; increases enzyme activity in drug-sensitive cell line HL-60, but not in drug-resistant HL-60/ADR cell line; regulation of intracellular ceramide is closely related to drug resistance and DOX-induced apoptosis
eliglustat
-
-
ethyl-2-amino-6-bromo-(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
-
Genz-112638
-
inhibitor is tested in a murine model of Gaucher disease (D409V/null): mice that receive drug prior to significant accumulation of substrate show reduced levels of glucosylceramide and number of Gaucher cells in the spleen, lung and liver when compared to control. Treatment of older mice that already display significant amounts of tissue glucosylceramide results in arrest of further accumulation of the substrate and appearance of additional Gaucher cells in affected organs; substrate inhibition therapy with Genz-112638 represents an approach to enzyme therapy to treat the visceral pathology in Gaucher diseases
Genz-682452
-
a mall molecule inhibitor of enzyme GCS, that can traverse the bloodbrain barrier. Treating Fabry mice with Genz-682452 results in reduced tissue levels of including globotriaosylceramide and lysoglobotriaosylceramide and a delayed loss of the thermal nociceptive response. Greatest improvements are realized when the therapeutic intervention is administered to younger mice before they developed overt pathology
-
N-(5'-adamantan-1'-yl-methoxy)-pentyl-1-deoxynojirimycin
-
highly specific small molecule inhibitor of glucosylceramide synthase. When administered to mice and rats, it significantly reduces glycosphingolipid but not ceramide concentrations in various tissues. Treatment of ob/ob mice with the inhibitor normalizes their elevated tissue glucosylceramide levels, markedly lowers circulating glucose levels, improves oral glucose tolerance, reduced A1C, and improves insulin sensitivity in muscle and liver
N-(5'-adamantane-1'-yl-methoxy)-pentyl-1-deoxynojirimycin
-
pharmacological inhibition of glucosylceramide synthase enhances insulin sensitivity
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-butyl 1-deoxynojirimycin
-
-
N-butyl-1-deoxynojirimycin
-
-
N-butyl-2,4-di-O-butyl-1,5-dideoxy-1,5-imino-D-glucitol
-
1 mM, 29% inhibition
N-butyldeoxynojirimycin
N-ethylmaleimide
-
attacks Cys207
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-[(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
-
-
N-[5-(adamantan-1-yl-ethoxy)-pentyl]-L-ido-1-deoxynojirimycin
-
-
N-[5-(adamantan-1-yl-methoxy)-pentyl]-1-deoxynojirimycin
N-[5-(adamantan-1-yl-methoxy)-pentyl]-L-ido-1-deoxynojirimycin
-
-
octyl glucoside
-
high concentration
octyl thioglucoside
-
-
Phospholipase A
-
treatment of microsomes results in loss of enzyme actvity
-
Phospholipase C
-
treatment of microsomes results in loss of enzyme actvity
-
PP55B
-
i.e. isopropylidene derivative of 5'-O-[[(2-decanoylamino-3-phenylpropylloxycarbonyl)amino]sulfonyl]uridine, 21% inhibition at 0.2 mM
threo-1-phenyl-2-decanoyl-amino-3-morpholino-1-propanol
-
inhibition at 0.005 mM
Triton X-100
Trypsin
-
-
-
Zwittergent 3-12
-
complete inhibition
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
-
CHAPS
cycloserine
-
induction
Detergent
-
dioleoyl phosphatidylcholine
-
or other exogenous phospholipid, required for activity
HSP70
-
L-threo-1-phenyl-2-decanoylamino-3-morpholino-1-propanol
-
L-PDMP treatment induces a 2.4 increase in glucosylceramide
NAD+
-
stimulation, best at 2 mM
NADP+
-
stimulation
NADPH
-
stimulation
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.04055
C6-ceramide
-
in tumor of NCI/ADR-RES
0.054 - 0.292
ceramide
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 - 0.2
UDP-glucose
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0045
ethyl-2-amino-6-bromo-(1-cyano-2-ethoxy-2-oxoethyl)-4H-chromene-3-carboxylate
-
pH 7.5, 30C
-
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
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
-
-
0.00002
(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
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
0.000003
(2R,3R,4R,5S)-1-[5-[(4,8-dihydropyren-1-yl)methoxy]pentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol
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
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
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
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
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
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
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
0.000024
Genz-112638
Mus musculus
-
-
0.02 - 0.04
N,N'-(5,5'-[2-(adamantan-1-yl)propane-1,3-diyl]bis-(oxy)bis(pentane-5,1-diyl))-bis(1-deoxynojirimycin)
0.01 - 0.02
N,N'-(5,5'-[2-(adamantan-1-yl)propane-1,3-diyl]bis-(oxy)bis(pentane-5,1-diyl))-bis(L-ido-1-deoxynojirimycin)
0.02 - 0.04
N,N'-(5,5'-[adamantan-1,3-diylbis(methylene)]bis(oxy)-bis(pentane-5,1-diyl))-bis(1-deoxynojirimycin)
0.005 - 0.01
N,N'-(5,5'-[adamantan-1,3-diylbis(methylene)]bis(oxy)-bis(pentane-5,1-diyl))-bis(L-ido-1-deoxynojirimycin)
0.0002
N-adamantanemethoxypentyldeoxynojirimycin
Homo sapiens
-
pH 5.2, 37C
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
0.164
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
-
-
0.0008
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, 37C
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, 37C
0.0008
N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-1-hydroxy-3-(morpholin-4-yl)propan-2-yl]nonanamide
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, 37C
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, 37C
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, 37C
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
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
0.001 - 0.005
N-[5-(adamantan-1-yl-ethoxy)-pentyl]-1-deoxynojirimycin
0.005
N-[5-(adamantan-1-yl-ethoxy)-pentyl]-L-ido-1-deoxynojirimycin
Mus musculus
-
in vitro inhibition of purified enzyme
0.0002 - 0.0005
N-[5-(adamantan-1-yl-methoxy)-pentyl]-1-deoxynojirimycin
0.0001
N-[5-(adamantan-1-yl-methoxy)-pentyl]-L-ido-1-deoxynojirimycin
Mus musculus
-
in vivo inhibition of a cell culture
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.00000034
-
CHO cell line mutant Z65
0.00000139
-
CHO cell line K-1
0.0000065
-
-
0.0000082
-
whole epidermis
0.00017
-
recombinant enzyme in cell extract of cell line KB-3-1
0.0002
-
microsomal fraction, 30C
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
0.0007
-
Golgi fraction
0.0436
-
purified enzyme
additional information
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.4 - 6.5
-
MES or Tris-maleate buffer
7.5
-
assay at
8
-
assay at
8.2
-
brain
additional information
-
sharp fall of activity below and above pH 6.5
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7 - 8.5
-
-
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
25 - 32
-
assay at
TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
15 - 40
-
-
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
high enzyme expression level and content
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
-
strain K1, and GM3-mutant strain Z65
Manually annotated by BRENDA team
-
ovary cells expressing the LT antigen
Manually annotated by BRENDA team
-
high enzyme expression level and content
Manually annotated by BRENDA team
-
80% of the activity in outer epidermis, 20% in lower epidermis
Manually annotated by BRENDA team
-
cerebellar granule cells are treated with GCS inhibitor D-threo-2-palmitoylamino-3-pyrrolidino-1-propanol which induces an increase in log-chain ceramides, loss of viability and dramatic changes in neuron/neurite morphology
Manually annotated by BRENDA team
-
highest activity
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
-
vinorelbine-resistant, high expression of enzyme GCS in lung cancer cells resistant to vinorelbine-induced apoptosis
Manually annotated by BRENDA team
-
mRNA
Manually annotated by BRENDA team
-
peripheral blood cell of leukaemic patients before chemotherapy
Manually annotated by BRENDA team
-
mRNA
Manually annotated by BRENDA team
-
U2OS-AS cell, construction of the pHA-E6S and pHA-E6AS plasmids, which respectively contain either the sense or the antisense versions of epitope-tagged E6 (HA-E6) under the control of the CMV promoter, and establishment of the U2OSE64b and U2OSE6AS cell lines by stable transfection with these plasmids has been described previously; U2OS-E6b4 cell, construction of the pHA-E6S and pHA-E6AS plasmids, which respectively contain either the sense or the antisense versions of epitope-tagged E6 (HA-E6) under the control of the CMV promoter, and establishment of the U2OSE64b and U2OSE6AS cell lines by stable transfection with these plasmids has been described previously
Manually annotated by BRENDA team
additional information
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
-
perinuclear and membranes
Manually annotated by BRENDA team
additional information
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
66000
-
sedimentation in a glycerol gradient
additional information
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
brain enzyme, half-life: 50 min at various temperatures
-
glycerol stabilizes
-
labile enzyme
-
NAD+ stabilizes
-
no loss of activity during freezing and subsequent thawing
-
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-70C, 0.2 M MOPS, 0.25 M sucrose, pH 6.5, stable for more than 3 months
-
-70C, enzyme in intact kidneys is stable for at least 90 days
-
4C, enzyme in intact kidneys, 53% loss of activity after overnight storage
-
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
partial from Golgi membranes
-
partial from Golgi membranes; solubilization method
-
solubilization method
-
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
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; functional expression in Escherichia coli BL21(DE3)
-
cloning from CHO cell line K1, overexpression in GM3-mutant CHO cell line Z65, DNA and amino acid sequence determination
-
cloning from rat brain genetic library and expression in Escherichia coli BL21(DE3)
-
cloning of wild-type and construction of knock-out mutant, functional expression in Saccharomyces cerevisiae strain 334, expression of wild-type leads to accumulation of beta-D-glucopyranosyl ceramides, absent in wild-type Saccharomyces cerevisiae, knock-out mutation is not lethal
-
expressed as recombinant protein
-
expressed in different drug-resistant human cancer cell lines
-
expressed in GM95 cells deficient in glycosphingolipids
-
expressed in PC12 cells
-
expression in an enzyme-deficient strain of Pichia pastoris
-
expression in Saccharomyces cerevisiae
Q58FH5
expression of enzyme gene in antisense orientation, two-hybrid system: coexpression with the reticulon RTN family, interaction especially with RTN-1C
-
expression of wild-type and mutants in Escherichia coli BL21(DE3)
-
functional expression in Escherichia coli BL21(DE3)
-
functional expression in membranes of a Pichia pastoris enzyme-deficient double-null mutant strain, also lacking sterol glucosyltransferase activity
-
functional expression in Saccharomyces cerevisiae strain 334
-
functional expression of 1 isozyme in Saccharomyces cerevisiae strain 334
-
gene GlcT-1, DNA sequence determination and analysis, functional expression in enzyme-deficient GM-95 cells, expression as V5/His-tagged protein in GM95 cells
-
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
after 17 h under a 42C heat stress, GluT mRNA increased to 142%
-
after 24 h under a 42C heat stress, GluT mRNA significantly increased to 714%; cell culture under 42C heat stress for 24 h, increase of gene expression to 714%
-
cell culture under 42C heat stress for 17 h, increase of gene expression to 142%
-
glucosylceramide synthase expression is enhanced in breast cancer stem cells but not in normal mammary epithelial stem cells
-
HSP70 influence on gene expression
in the absence of p53, mitomycin C treatment elicits a down-regulation of the enzyme
-
the mixed-backbone oligonucleotide MBO-asGCS considerable decreases mRNA levels in murine tumor cell lines
-
the mixed-backbone oligonucleotide MBO-asGCS decreases mRNA levels in human tumor cell lines by 65%
-
Vinca alkaloid vinorelbine induces the enzyme in vinorelbine-resitant cells
-
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
DELTAFgGCS1
-
a null mutation of the FgGCS1 gene becomes resistant to antifungal defensins MsDef1, but not to MtDef4 from Medicago. It shows a significant change in the conidial morphology and displays dramatic polar growth defect, and its mycelia are resistant to cell wall degrading enzymes.GCS1 is not required for pathogenicity of Fusarium graminearum
C143A
-
site-directed mutagenesis, increased activity, reduced expression level compared to wild-type
C207A
-
site-directed mutagenesis, reduced activity, reduced inhibitory effect of N-ethylmaleimide, reduced expression level compared to wild-type
C213A
-
site-directed mutagenesis, reduced activity, reduced expression level compared to wild-type
C232A
-
site-directed mutagenesis, reduced expresssion level compared to wild-type
C290A
-
site-directed mutagenesis, reduced expression level compared to wild-type
C296A
-
site-directed mutagenesis, reduced activity, reduced expression level compared to wild-type
C321A
-
site-directed mutagenesis, reduced activity
C321A/C323A
-
site-directed mutagenesis, reduced activity
C343A
-
site-directed mutagenesis, enhanced activity, slightly reduced expression level compared to wild-type
C384A
-
site-directed mutagenesis, enhanced activity
C86A
-
site-directed mutagenesis, reduced activity, reduced expression level compared to wild-type
C98A
-
site-directed mutagenesis, reduced activity, reduced expression level compared to wild-type
H169A
-
26.4% activity compared to wild-type, reduced inhibition by diethyldicarbonate and increased protection by UDP-glucose
H193A
-
33.0% activity compared to wild-type, reduced inhibition by diethyldicarbonate and reduced protection by UDP-glucose
H193D
-
no activity
H193N
-
23.0% activity compared to wild-type, reduced inhibition by diethyldicarbonate and reduced protection by UDP-glucose
H193R
-
no activity
H26A
-
5.2% activity compared to wild-type
H26D
-
10.5% activity compared to wild-type
H26N
-
44.5% activity compared to wild-type
H26R
-
118.5% activity compared to wild-type, slightly enhanced inhibition by diethyldicarbonate and slightly reduced protection by UDP-glucose
H308A
-
35.2% activity compared to wild-type, slightly reduced inhibition by diethyldicarbonate and slightly reduced protection by UDP-glucose
H308A/H309A
-
10.8% activity compared to wild-type
H309A
-
69.1% activity compared to wild-type
H322A
-
3.8% activity compared to wild-type
H322D
-
2.6% activity compared to wild-type
H322N
-
49.8% activity compared to wild-type, slightly enhanced inhibition by diethyldicarbonate and slightly reduced protection by UDP-glucose
H322R
-
no activity
H36A
-
103.2% activity compared to wild-type, slightly enhanced inhibition by diethyldicarbonate and slightly reduced protection by UDP-glucose
H90A
-
119.3% activity compared to wild-type
additional information
Renatured/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
reconstitution of solubilized enzyme in detergent-free lipid vesicles
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
molecular biology
-
glucosylceramide is essential for MsDef1-mediated growth inhibition of Fusarium graminearum, but not for its pathogenicity
pharmacology
-
enzyme might be an attractive target for malarial chemotherapy
Show AA Sequence (134 entries)
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