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2.7.1.91: sphingosine kinase

This is an abbreviated version!
For detailed information about sphingosine kinase, go to the full flat file.

Word Map on EC 2.7.1.91

Reaction

ATP
+
a sphingoid base
=
ADP
 +
a sphingoid base 1-phosphate

Synonyms

dihydrosphingosine kinase, kinase, dihydrosphingosine (phosphorylating), kinase, sphingosine (phosphorylating), More, SGK, SK, SK-1, SK-2, SK1, SK2, sphinganine kinase, sphingoid base kinase, sphingosine kinase, sphingosine kinase 1, sphingosine kinase 2, sphingosine kinase type 1, sphingosine kinase type 2, sphingosine kinase-1, sphingosine kinase-2, SPHK, SPHK-1, SPHK1, SPHK1a, SPHK1b, SPHK2, SPK

ECTree

     2 Transferases
         2.7 Transferring phosphorus-containing groups
             2.7.1 Phosphotransferases with an alcohol group as acceptor
                2.7.1.91 sphingosine kinase

Inhibitors

Inhibitors on EC 2.7.1.91 - sphingosine kinase

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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(1S)-1-(2-fluorophenyl)-1,2,3,4-tetrahydroisoquinoline-6,7-diol
i.e. ZINC19691372
-
(1S,3R)-1-(3,4-dihydroxyphenyl)-2,3,4,9-tetrahydro-1H-b-carboline-3-carboxylic acid
i.e. ZINC00095976
-
(2R)-1-[5-methoxy-2-([[2-(methylsulfanyl)ethyl]amino]methyl)phenoxy]-3-(4-methylpiperazin-1-yl)propan-2-ol
i.e. ZINC20254629
-
(2R)-2-amino-4-(4-octylphenyl)butan-1-ol
-
i.e. (R)-2-amino-4-(4-octylphenyl)butan-1-ol, synthetic sphingosine analogue, specific inhibition of isozymes SphK1 and SphK2
(2R,3S)-2-[[(4-octylphenyl)amino]methyl]pyrrolidin-3-ol
-
inhibition of isoform Sk1
(2R,3S)-3-amino-4-morpholin-4-yl-1-phenylbutan-2-ol
-
i.e. (2R,3S)-3-amino-4-morpholino-1-phenylbutan-2-ol, synthetic sphingosine analogue, specific inhibition of isozymes SphK1 and SphK2
(2R,3S,4E)-N-methyl-5-(4'-pentylphenyl)-2-aminopent-4-ene-1,3-diol
-
potent, water-soluble, isoenzyme-specific inhibitor of SphK1. The inhibitor decreases growth and survival of human leukemia U937 and Jurkat cells, and enhances apoptosis and cleavage of Bcl-2. Lethality of SK1-I is reversed by caspase inhibitors and by expression of Bcl-2. The specific inhibitor of SphK1 warrants attention as potential addition to the therapeutic armamentarium in leukemia
(2R,3S,4E)-N-methyl-5-(4-pentylphenyl)-2-aminopent-4-ene-1,3-diol
(2R,4S)-2-(hydroxymethyl)-1-[2-[4-([4-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]amino)phenyl]ethyl]piperidin-4-ol
-
-
(2S)-1-(1,3-benzodioxol-5-yloxy)-3-[benzyl(2-hydroxyethyl)amino]propan-2-ol
i.e. ZINC03253280
-
(2S)-1-(3-dodecylbenzoyl)pyrrolidine-2-carboximidamide
-
-
(2S)-1-(4-dodecylbenzoyl)pyrrolidine-2-carboximidamide
-
(2S)-1-(4-[4-[3-(2-cyclohexylethyl)phenyl]-1,3-oxazol-2-yl]benzoyl)pyrrolidine-2-carboximidamide
-
-
(2S)-1-(azepan-1-yl)-3-(1,3-benzodioxol-5-yloxy)propan-2-ol
i.e. ZINC02686881
-
(2S)-1-[3-[7-(cyclohexylmethoxy)heptyl]benzoyl]pyrrolidine-2-carboximidamide
-
-
(2S)-2-(3-[6-[(3-bromophenyl)methoxy]naphthalen-2-yl]-1,2,4-oxadiazol-5-yl)pyrrolidine-1-carboximidamide
isoform SphK2 shows 35% residual activity at 0.001 mM
-
(2S)-2-(3-[6-[(3-chlorophenyl)methoxy]naphthalen-2-yl]-1,2,4-oxadiazol-5-yl)pyrrolidine-1-carboximidamide
isoform SphK2 shows 46% residual activity at 0.001 mM
-
(2S)-2-(3-[6-[(4-bromophenyl)methoxy]naphthalen-2-yl]-1,2,4-oxadiazol-5-yl)pyrrolidine-1-carboximidamide
isoform SphK2 shows 49% residual activity at 0.001 mM
-
(2S)-2-(3-[6-[(4-chlorophenyl)methoxy]naphthalen-2-yl]-1,2,4-oxadiazol-5-yl)pyrrolidine-1-carboximidamide
isoform SphK2 shows 56% residual activity at 0.001 mM
-
(2S)-2-(3-[6-[(4-cyanophenyl)methoxy]naphthalen-2-yl]-1,2,4-oxadiazol-5-yl)pyrrolidine-1-carboximidamide
isoform SphK2 shows 43% residual activity at 0.001 mM
-
(2S)-2-(3-[6-[(4-methylphenyl)methoxy]naphthalen-2-yl]-1,2,4-oxadiazol-5-yl)pyrrolidine-1-carboximidamide
isoform SphK2 shows 94% residual activity at 0.001 mM
-
(2S)-2-(3-[6-[([1,1'-biphenyl]-4-yl)methoxy]naphthalen-2-yl]-1,2,4-oxadiazol-5-yl)pyrrolidine-1-carboximidamide
isoform SphK2 shows 51% residual activity at 0.001 mM
-
(2S)-2-(3-[6-[2-([1,1'-biphenyl]-4-yl)-2-oxoethoxy]naphthalen-2-yl]-1,2,4-oxadiazol-5-yl)pyrrolidine-1-carboximidamide
isoform SphK2 shows 77% residual activity at 0.001 mM
-
(2S)-2-([3-[4-([4-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]amino)phenyl]-1,2,4-oxadiazol-5-yl]methyl)pyrrolidine-1-carboximidamide
potent and selective isoform SphK2 inhibitor
-
(2S)-2-amino-N-(4-octylphenyl)-4-hydroxybutanamide
-
inhibition of isoform Sk1
(2S)-2-[(pyridin-4-ylmethyl)amino]butan-1-ol
i.e. ZINC05823226
-
(2S)-2-[3-(6-butoxynaphthalen-2-yl)-1,2,4-oxadiazol-5-yl]pyrrolidine-1-carboximidamide
isoform SphK2 shows 69% residual activity at 0.001 mM
-
(2S)-2-[3-(6-[2-oxo-2-[4-(trifluoromethyl)phenyl]ethoxy]naphthalen-2-yl)-1,2,4-oxadiazol-5-yl]pyrrolidine-1-carboximidamide
isoform SphK2 shows 65% residual activity at 0.001 mM
-
(2S)-2-[3-(6-[2-[2-(trifluoromethyl)phenyl]ethoxy]naphthalen-2-yl)-1,2,4-oxadiazol-5-yl]pyrrolidine-1-carboximidamide
isoform SphK2 shows 47% residual activity at 0.001 mM
-
(2S)-2-[3-(6-[2-[3-(trifluoromethyl)phenyl]ethoxy]naphthalen-2-yl)-1,2,4-oxadiazol-5-yl]pyrrolidine-1-carboximidamide
isoform SphK2 shows 34% residual activity at 0.001 mM
-
(2S)-2-[3-(6-[2-[4-(trifluoromethyl)phenyl]ethoxy]naphthalen-2-yl)-1,2,4-oxadiazol-5-yl]pyrrolidine-1-carboximidamide
isoform SphK2 shows 30% residual activity at 0.001 mM
-
(2S)-2-[3-(6-[[3-(trifluoromethyl)phenyl]methoxy]naphthalen-2-yl)-1,2,4-oxadiazol-5-yl]pyrrolidine-1-carboximidamide
isoform isoform SphK2 shows 81% residual activity at 0.001 mM
-
(2S)-2-[3-(6-[[4-(trifluoromethyl)phenyl]methoxy]naphthalen-2-yl)-1,2,4-oxadiazol-5-yl]pyrrolidine-1-carboximidamide
SLC5091592, isoform SphK2 shows 42% residual activity at 0.001 mM
-
(2S)-2-[3-[3-(trifluoromethyl)-4-[[4-(trifluoromethyl)phenyl]methoxy]phenyl]-1,2,4-oxadiazol-5-yl]pyrrolidine-1-carboximidamide
potent and selective isoform SphK2 inhibitor
-
(2S)-2-[3-[4-(octyloxy)-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl]pyrrolidine-1-carboximidamide
SLM6031434, the inhibitor is 23fold selective for isoform SphK2 over SphK1 with 51% inhibition of isoform SphK2 at 0.0003 mM
-
(2S)-2-[3-[4-(octyloxy)phenyl]-1,2,4-oxadiazol-5-yl]pyrrolidine-1-carboximidamide
8% inhibition of isoform SphK2 at 0.001 mM
-
(2S)-2-[3-[6-(2-methoxyethoxy)naphthalen-2-yl]-1,2,4-oxadiazol-5-yl]pyrrolidine-1-carboximidamide
isoform SphK2 shows 87% residual activity at 0.001 mM
-
(2S)-2-[3-[6-(2-methylpropoxy)naphthalen-2-yl]-1,2,4-oxadiazol-5-yl]pyrrolidine-1-carboximidamide
isoform SphK2 shows 74% residual activity at 0.001 mM
-
(2S)-2-[3-[6-(benzyloxy)naphthalen-2-yl]-1,2,4-oxadiazol-5-yl]pyrrolidine-1-carboximidamide
isoform SphK2 shows 97% residual activity at 0.001 mM
-
(2S)-2-[3-[6-(cyclopentylmethoxy)naphthalen-2-yl]-1,2,4-oxadiazol-5-yl]pyrrolidine-1-carboximidamide
isoform SphK2 shows 57% residual activity at 0.001 mM
-
(2S)-2-[3-[6-(heptyloxy)naphthalen-2-yl]-1,2,4-oxadiazol-5-yl]pyrrolidine-1-carboximidamide
isoform SphK2 shows 83% residual activity at 0.001 mM
-
(2S)-2-[3-[6-(hexyloxy)naphthalen-2-yl]-1,2,4-oxadiazol-5-yl]pyrrolidine-1-carboximidamide
SLC5011416, isoform SphK2 shows 64% residual activity at 0.001 mM; SLC5091592, isoform SphK2 shows 42% residual activity at 0.001 mM
-
(2S)-2-[3-[6-(pentyloxy)naphthalen-2-yl]-1,2,4-oxadiazol-5-yl]pyrrolidine-1-carboximidamide
SLC5081308, isoform SphK2 shows 51% residual activity at 0.001 mM
-
(2S)-2-[[(2R)-3-(9H-carbazol-9-yl)-2-hydroxypropyl]amino]butanedioic acid
i.e. ZINC02707482
-
(2S,3R)-2-amino-4-(4-octylphenyl)butane-1,3-diol
-
i.e. (2S,3R)-2-amino-4-(4-octylphenyl)butane-1,3-diol, synthetic sphingosine analogue, specific inhibition of isozymes SphK1 and SphK2
(2S,3R)-2-amino-N-(4-octylphenyl)-3-hydroxybutanamide
-
inhibition of isoform Sk1
(2S,3R,4E)-2-(dimethylamino)octadec-4-ene-1,3-diol
inhibits both isoforms SK1 and SK2. Treatment triples the levels of isoform SK1 mRNA, but only slightly increases isoform SK2 expression; inhibits both isoforms SK1 and SK2. Treatment triples the levels of isoform SK1 mRNA, but only slightly increases isoform SK2 expression
(2S,3S)-2-amino-4-(4-octylphenyl)butane-1,3-diol
-
i.e. (2S,3S)-2-amino-4-(4-octylphenyl)butane-1,3-diol, synthetic sphingosine analogue, specific inhibition of isozymes SphK1 and SphK2
(2S,3S)-3-hydroxy-2-[3-[6-(2-methylpropoxy)naphthalen-2-yl]-1,2,4-oxadiazol-5-yl]pyrrolidine-1-carboximidamide
SLC5121314, isoform SphK2 shows 53% residual activity at 0.001 mM
-
(2S,3S)-3-hydroxy-2-[3-[6-(pentyloxy)naphthalen-2-yl]-1,2,4-oxadiazol-5-yl]pyrrolidine-1-carboximidamide
SLC5111312, isoform SphK2 shows 46% residual activity at 0.001 mM
-
(2S,3S)-3-hydroxy-N-(4-octylbenzyl)pyrrolidine-2-carboxamide
-
inhibition of isoform Sk1
(2S,3S)-3-hydroxy-N-(4-octylphenyl)pyrrolidine-2-carboxamide
-
inhibition of isoform Sk1
(3aR,4S,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carboxylic acid
i.e. ZINC05033974
-
(3R)-1-[2-(4-octylphenyl)ethyl]pyrrolidin-3-ol
-
(3R,4R,5S)-2-(6-amino-9H-purin-9-yl)-5-methyltetrahydrofuran-3,4-diol
i.e. ZINC17005625
-
(3S)-1-([4-[(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)methyl]phenyl]methyl)pyrrolidin-3-ol
-
-
(3S)-1-[2-(4-octylphenyl)ethyl]pyrrolidin-3-ol
-
(3S)-N-[(1S)-1-[4-[5-(2-cyclohexylethyl)-1,2,4-oxadiazol-3-yl]phenyl]propyl]-3-hydroxy-L-prolinamide
-
-
(4-dodecylphenyl)(4-hydroxypiperidin-1-yl)methanone
-
(4-dodecylphenyl)[(2R)-2-(hydroxymethyl)pyrrolidin-1-yl]methanone
-
(4-dodecylphenyl)[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]methanone
-
(4R)-4-(4-hydroxy-3-methoxyphenyl)-7-methoxy-1,2,3,4-tetrahydroisoquinolin-6-ol
i.e. ZINC01719191
-
(4R)-N4-(6-methoxyquinolin-8-yl)pentane-1,4-diamine
i.e. ZINC01530863
-
(5Z)-3-(2-aminoethyl)-5-[3-(4-butoxyphenyl)propylidene]-1,3-thiazolidine-2,4-dione
-
(E)-3-(3-(4-((4-(4-chlorophenyl)pyrimidin-2-yl)amino)phenyl)-3-oxoprop-1-en-1-yl)-6-methoxyquinolin-2(1H)-one
-
-
(E)-6,7-dimethoxy-3-(3-(4-((4-(naphthalen-2-yl)pyrimidin-2-yl)amino)phenyl)-3-oxoprop-1-en-1-yl)quinolin-2(1H)-one
-
-
(E)-6-methoxy-3-(3-(4-((4-(naphthalen-2-yl)pyrimidin-2-yl)amino)phenyl)-3-oxoprop-1-en-1-yl)quinolin-2(1H)-one
-
-
(R)-2-(3-(4-octylphenyl)-1,2,4-oxadiazol-5-yl)pyrrolidine-1-carboximidamide
-
(R)-amino(2-((4-decylphenyl)carbamoyl)pyrrolidin-1-yl)-methaniminium 2,2,2-trifluoroacetate
-
(R)-amino(3-(3-(4-octylphenyl)-1,2,4-oxadiazol-5-yl)-pyrrolidin-1-yl)methaniminium
-
(R)-FTY720-OMe
(S)-1-(1-(3-(4-octylphenyl)-1,2,4-oxadiazol-5-yl)ethyl)-guanidine
-
(S)-1-(2-methyl-1-(3-(4-octylphenyl)-1,2,4-oxadiazol-5-yl)-propyl)guanidine
-
(S)-1-(4-dodecylbenzoyl)pyrrolidine-2-carboximidamide
-
(S)-2-((3-(4-((4-(1-methyl-1H-pyrazol-4-yl)-1H-1,2,3-triazol-1-yl)methyl)phenyl)-1,2,4-oxadiazol-5-yl)methyl)pyrrolidine-1-carboximidamide
-
-
(S)-2-((3-(4-((4-(4-(trifluoromethyl)phenyl)-1H-1,2,3-triazol-1-yl)methyl)phenyl)-1,2,4-oxadiazol-5-yl)methyl)-pyrrolidine-1-carboximidamide
-
-
(S)-2-((3-(4-((4-(4-(trifluoromethyl)phenyl)-1H-1,2,3-triazol-1-yl)methyl)phenyl)-1,2,4-oxadiazol-5-yl)pyrrolidine-1-carboximidamide
-
-
(S)-2-((3-(4-((4-(4-fluorophenyl)-1H-1,2,3-triazol-1-yl)methyl)phenyl)-1,2,4-oxadiazol-5-yl)-pyrrolidine-1-carboximidamide
-
-
(S)-2-((3-(4-((4-(4-methoxyphenyl)-1H-1,2,3-triazol-1-yl)methyl)phenyl)-1,2,4-oxadiazol-5-yl)-pyrrolidine-1-carboximidamide
-
-
(S)-2-((3-(4-((4-(4-methoxyphenyl)-1H-1,2,3-triazol-1-yl)methyl)phenyl)-1,2,4-oxadiazol-5-yl)methyl)pyrrolidine-1-carboximidamide
-
-
(S)-2-((3-(4-((4-(pyridin-2-yl)-1H-1,2,3-triazol-1-yl)methyl)phenyl)-1,2,4-oxadiazol-5-yl)methyl)pyrrolidine-1-carboximidamide
-
-
(S)-2-((3-(4-((4-(thiophen-2-yl)-1H-1,2,3-triazol-1-yl)methyl)phenyl)-1,2,4-oxadiazol-5-yl)-pyrrolidine-1-carboximidamide
-
-
(S)-2-((3-(4-((4-butyl-1H-1,2,3-triazol-1-yl)methyl)phenyl)-1,2,4-oxadiazol-5-yl)methyl)pyrrolidine-1-carboximidamide
-
-
(S)-2-((3-(4-((4-butyl-1H-1,2,3-triazol-1-yl)methyl)phenyl)-1,2,4-oxadiazol-5-yl)pyrrolidine-1-carboximidamide
-
-
(S)-2-((3-(4-((4-cyclopropyl-1H-1,2,3-triazol-1-yl)methyl)phenyl)-1,2,4-oxadiazol-5-yl)methyl)pyrrolidine-1-carboximidamide
-
-
(S)-2-((3-(4-((4-cyclopropyl-1H-1,2,3-triazol-1-yl)methyl)phenyl)-1,2,4-oxadiazol-5-yl)pyrrolidine-1-carboximidamide
-
-
(S)-2-((3-(4-((4-phenyl-1H-1,2,3-triazol-1-yl)methyl)phenyl)-1,2,4-oxadiazol-5-yl)pyrrolidine-1-carboximidamide
-
-
(S)-2-((3-(4-((4-phenyl-1H-1,2,3-triazol-1-yl)methyl)phenyl)-1,2,4-oxadiazol-5yl)methyl)pyrrolidine-1-carboximidamide
-
-
(S)-2-(3-(2-(trifluoromethyl)-4-((4-(trifluoromethyl)-benzyl)oxy)phenyl)-1,2,4-oxadiazol-5-yl)pyrrolidine-1-carboximidamide
35% inhibition of isoform SphK2 at 0.0003 mM
-
(S)-2-(3-(2-chloro-4-((4-(trifluoromethyl)benzyl)oxy)-phenyl)-1,2,4-oxadiazol-5-yl)pyrrolidine-1-carboximidamide
40% inhibition of isoform SphK2 at 0.0003 mM
-
(S)-2-(3-(3,5-dimethyl-4-((4-(trifluoromethyl)benzyl)-oxy)phenyl)-1,2,4-oxadiazol-5-yl)pyrrolidine-1-carboximidamide
23% inhibition of isoform SphK2 at 0.0003 mM
-
(S)-2-(3-(3-(pyridin-4-yl)-4-((4-(trifluoromethyl)-benzyl)oxy)phenyl)-1,2,4-oxadiazol-5-yl)pyrrolidine-1-carboximidamide
8% inhibition of isoform SphK2 at 0.0003 mM
-
(S)-2-(3-(3-(tert-butyl)-4-((4-(trifluoromethyl)benzyl)-oxy)phenyl)-1,2,4-oxadiazol-5-yl)pyrrolidine-1-carboximidamide
66% inhibition of isoform SphK2 at 0.0003 mM
-
(S)-2-(3-(3-(trifluoromethyl)-4-((4-(trifluoromethyl)-benzyl)oxy)phenyl)-1,2,4-oxadiazol-5-yl)pyrrolidine-1-carboximidamide
SLM6071469, the inhibitor is 73fold selective for isoform SphK2 over SphK1 with 65% inhibition of isoform SphK2 at 0.0003 mM
-
(S)-2-(3-(3-allyl-4-((4-(trifluoromethyl)benzyl)oxy)-phenyl)-1,2,4-oxadiazol-5-yl)pyrrolidine-1-carboximidamide
59% inhibition of isoform SphK2 at 0.0003 mM
-
(S)-2-(3-(3-bromo-4-((4-(trifluoromethyl)benzyl)oxy)-phenyl)-1,2,4-oxadiazol-5-yl)pyrrolidine-1-carboximidamide
24% inhibition of isoform SphK2 at 0.0003 mM
-
(S)-2-(3-(3-chloro-4-((4-(trifluoromethyl)benzyl)oxy)-phenyl)-1,2,4-oxadiazol-5-yl)pyrrolidine-1-carboximidamide
33% inhibition of isoform SphK2 at 0.0003 mM
-
(S)-2-(3-(3-cyclopropyl-4-((4-(trifluoromethyl)-benzyl)oxy)phenyl)-1,2,4-oxadiazol-5-yl)pyrrolidine-1-carboximidamide
52% inhibition of isoform SphK2 at 0.0003 mM
-
(S)-2-(3-(3-ethyl-4-((4-(trifluoromethyl)benzyl)oxy)-phenyl)-1,2,4-oxadiazol-5-yl)pyrrolidine-1-carboximidamide
42% inhibition of isoform SphK2 at 0.0003 mM
-
(S)-2-(3-(3-fluoro-4-((4-(trifluoromethyl)benzyl)oxy)-phenyl)-1,2,4-oxadiazol-5-yl)pyrrolidine-1-carboximidamide
23% inhibition of isoform SphK2 at 0.0003 mM
-
(S)-2-(3-(3-isopropyl-4-((4-(trifluoromethyl)benzyl)-oxy)phenyl)-1,2,4-oxadiazol-5-yl)pyrrolidine-1-carboximidamide
67% inhibition of isoform SphK2 at 0.0003 mM
-
(S)-2-(3-(3-methoxy-4-((4-(trifluoromethyl)benzyl)-oxy)phenyl)-1,2,4-oxadiazol-5-yl)pyrrolidine-1-carboximidamide
15% inhibition of isoform SphK2 at 0.0003 mM
-
(S)-2-(3-(3-methyl-4-((4-(trifluoromethyl)benzyl)oxy)-phenyl)-1,2,4-oxadiazol-5-yl)pyrrolidine-1-carboximidamide
3% inhibition of isoform SphK2 at 0.0003 mM
-
(S)-2-(3-(3-nitro-4-((4-(trifluoromethyl)benzyl)oxy)-phenyl)-1,2,4-oxadiazol-5-yl)pyrrolidine-1-carboximidamide
33% inhibition of isoform SphK2 at 0.0003 mM
-
(S)-2-(3-(3-propyl-4-((4-(trifluoromethyl)benzyl)oxy)-phenyl)-1,2,4-oxadiazol-5-yl)pyrrolidine-1-carboximidamide
60% inhibition of isoform SphK2 at 0.0003 mM
-
(S)-2-(3-(4'-fluoro-6-((4-(trifluoromethyl)benzyl)oxy)-[1,1'-biphenyl]-3-yl)-1,2,4-oxadiazol-5-yl)pyrrolidine-1-carboximidamide
31% inhibition of isoform SphK2 at 0.0003 mM
-
(S)-2-(3-(4-((4-(pyridin-2-yl)-1H-1,2,3-triazol-1-yl)methyl)phenyl)-1,2,4-oxadiazol-5-yl)pyrrolidine-1-carboximidamide
-
-
(S)-2-(3-(4-((4-(trifluoromethyl)benzyl)oxy)phenyl)-1,2,4-oxadiazol-5-yl)pyrrolidine-1-carboximidamide
2% inhibition of isoform SphK2 at 0.0003 mM
-
(S)-2-(3-(4-octylphenyl)-1,2,4-oxadiazol-5-yl)azetidine-1-carboximidamide
-
(S)-2-(3-(4-octylphenyl)-1,2,4-oxadiazol-5-yl)pyrrolidine-1-carboximidamide
-
(S)-2-(3-(4?-(trifluoromethyl)-6-((4-(trifluoromethyl)-benzyl)oxy)-[1,1'-biphenyl]-3-yl)-1,2,4-oxadiazol-5-yl)-pyrrolidine-1-carboximidamide
12% inhibition of isoform SphK2 at 0.0003 mM
-
(S)-2-(3-(6-((4-(trifluoromethyl)benzyl)oxy)-[1,1'-biphenyl]-3-yl)-1,2,4-oxadiazol-5-yl)pyrrolidine-1-carboximidamide
28% inhibition of isoform SphK2 at 0.0003 mM
-
(S)-2-(5-(4-octylphenyl)-1,3,4-oxadiazol-2-yl)pyrrolidin-1-ium 2,2,2-trifluoroacetate
-
(S)-amino((2-hydroxy-1-(3-(4-octylphenyl)-1,2,4-oxadiazol-5-yl)ethyl)amino)methaniminium
-
(S)-amino(2-((3-(4-octylphenyl)-1,2,4-oxadiazol-5-yl)-methyl)pyrrolidin-1-yl)methaniminium chloride
-
(S)-amino(2-((4-decylphenyl)carbamoyl)pyrrolidin-1-yl)-methaniminium 2,2,2-trifluoroacetate
-
(S)-amino(2-((4-octylbenzamido)methyl)pyrrolidin-1-yl)-methaniminium 2,2,2-trifluoroacetate
-
(S)-amino(2-((4-octylbenzyl)carbamoyl)pyrrolidin-1-yl)-methaniminium 2,2,2-trifluoroacetate
-
(S)-amino(2-(2-(3-(4-octylphenyl)-1,2,4-oxadiazol-5-yl)-ethyl)pyrrolidin-1-yl)methaniminium
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(S)-amino(2-(2-(3-(4-octylphenyl)-1,2,4-oxadiazol-5-yl)-ethyl)pyrrolidin-1-yl)methaniminium chloride
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(S)-amino(2-(3-(4-octylphenyl)-1,2,4-oxadiazol-5-yl)-2,5-di-hydro-1H-pyrrol-1-yl)methaniminium 2,2,2-trifluoroacetate
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(S)-amino(2-(3-(4-octylphenyl)-1,2,4-oxadiazol-5-yl)-piperidin-1-yl)methaniminium
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(S)-amino(2-(5-(4-octylphenyl)-1,2,4-oxadiazol-3-yl)-pyrrolidin-1-yl)methaniminium
-
(S)-FTY720 regioisomer
-
-
(S)-FTY720 vinylphosphonate
1-((3-(4-octylphenyl)-1,2,4-oxadiazol-5-yl)methyl)guanidine
-
1-(1-(3-(4-octylphenyl)-1,2,4-oxadiazol-5-yl)cyclopropyl)-guanidine
-
1-(3-(4-((4-(1-methyl-1H-pyrazol-5-yl)-1H-1,2,3-triazol-1-yl)methyl)phenyl)-1,2,4-oxadiazol-5-yl)cyclopropanecarboximidamide
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1-(3-(4-((4-cyclopropyl-1H-1,2,3-triazol-1-yl)methyl)phenyl)-1,2,4-oxadiazol-5-yl)cyclopropanecarboximidamide
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-
1-(3-(4-((4-phenyl-1H-1,2,3-triazol-1-yl)methyl)phenyl)-1,2,4-oxadiazol-5-yl)cyclopropanecarboximidamide
-
-
1-(4-dodecylphenethyl)piperidin-4-amine
-
1-(4-methylphenethyl)piperidin-4-amine
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1-(4-octylbenzyl)piperidin-4-ol
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1-(4-octylphenethyl)piperidin-4-amine
-
1-(4-octylphenethyl)piperidin-4-ol
a selective inhibitor of isozyme SK1, structure-activity relationship profile
1-carbamimidoyl-N-(3-dodecylphenyl)cyclopropane-1-carboxamide
-
-
1-methyl-1-((3-(4-octylphenyl)-1,2,4-oxadiazol-5-yl)methyl)-guanidine
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1-methyl-1-[2-[4-(4-octyl-1H-1,2,3-triazol-1-yl)phenyl]ethyl]piperidinium
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1-methyl-1-[2-[4-(4-pentyl-1H-1,2,3-triazol-1-yl)phenyl]ethyl]piperidinium
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1-methyl-2-[2-(4-octylphenyl)ethyl]pyridinium
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1-[2-(4-dodecylphenyl)ethyl]piperidin-4-ol
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1-[2-(4-hexylphenyl)ethyl]piperidin-4-ol
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1-[2-(4-octylphenyl)ethyl]piperidin-4-one
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1-[2-[4-(4-butyl-1H-1,2,3-triazol-1-yl)phenyl]ethyl]-1-methylpiperidinium
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1-[2-[4-(4-butyl-1H-1,2,3-triazol-1-yl)phenyl]ethyl]piperidin-4-ol
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1-[2-[4-(4-butyl-1H-1,2,3-triazol-1-yl)phenyl]ethyl]piperidine
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1-[2-[4-(4-octyl-1H-1,2,3-triazol-1-yl)phenyl]ethyl]piperidin-4-ol
-
1-[2-[4-(4-octyl-1H-1,2,3-triazol-1-yl)phenyl]ethyl]piperidine
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1-[2-[4-(4-pentyl-1H-1,2,3-triazol-1-yl)phenyl]ethyl]piperidin-4-ol
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1-[2-[4-(4-pentyl-1H-1,2,3-triazol-1-yl)phenyl]ethyl]piperidine
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1-[3-(3-decylphenyl)-1,2,4-oxadiazol-5-yl]cyclopropane-1-carboximidamide
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1-[3-(3-dodecylphenyl)-1,2,4-oxadiazol-5-yl]cyclopropane-1-carboximidamide
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1-[3-(3-tridecylphenyl)-1,2,4-oxadiazol-5-yl]cyclopropane-1-carboximidamide
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1-[3-(3-undecylphenyl)-1,2,4-oxadiazol-5-yl]cyclopropane-1-carboximidamide
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1-[3-(4-decylphenyl)-1,2,4-oxadiazol-5-yl]cyclopropane-1-carboximidamide
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1-[3-(4-dodecylphenyl)-1,2,4-oxadiazol-5-yl]cyclopropane-1-carboximidamide
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1-[3-(4-octylphenyl)propyl]piperidin-4-ol
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1-[3-(4-tridecylphenyl)-1,2,4-oxadiazol-5-yl]cyclopropane-1-carboximidamide
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-
1-[3-(4-undecylphenyl)-1,2,4-oxadiazol-5-yl]cyclopropane-1-carboximidamide
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1-[4-(4-octylphenyl)butyl]piperidin-4-ol
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1-[5-(3-dodecylphenyl)-1,2,4-oxadiazol-3-yl]cyclopropane-1-carboximidamide
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1-[5-(3-dodecylphenyl)-1,3,4-oxadiazol-2-yl]cyclopropane-1-carboximidamide
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1-[5-(4-dodecylphenyl)-1,2,4-oxadiazol-3-yl]cyclopropane-1-carboximidamide
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1-[5-(4-dodecylphenyl)-1,3,4-oxadiazol-2-yl]cyclopropane-1-carboximidamide
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1-[[4-(4-tert-butylphenoxy)-3-fluorophenyl]methyl]pyrrolidin-3-ol
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2-(4-hydroxy-6-oxo-1,6-dihydropyrimidin-2-yl)-N-(prop-2-en-1-yl)hydrazinecarbothioamide
i.e. ZINC12651592
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2-(4-hydroxy-6-oxo-1,6-dihydropyrimidin-2-yl)-N-phenylhydrazinecarbothioamide
i.e. ZINC19419587
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2-(4-hydroxyanilino)-4-(4-chlorophenyl)thiazole
2-(hydroxymethyl)-1-[2-[4-([4-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]amino)phenyl]ethyl]piperidin-4-ol
2-(p-hydroxyanilino)-4-(p-chlorophenyl) thiazole
2-(p-hydroxyanilino)-4-(p-chlorophenyl)thiazole
2-[(1R)-1-amino-2-methylpropyl]-6-hydroxypyrimidin-4(3H)-one
i.e. ZINC82450359
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2-[(1S)-1,2-diaminoethyl]-5-(diethylamino)phenol
i.e. ZINC72201085
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2-[(2S)-2-aminobutan-2-yl]-6-hydroxypyrimidin-4(3H)-one
i.e. ZINC82450459
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2-[(2S)-4-[(2-aminopyrimidin-5-yl)methyl]-1-[(2-methylphenyl)methyl]piperazin-2-yl]ethan-1-ol
i.e. ZINC19759036
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2-[2-(4-octylphenyl)ethyl]pyridine
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2-[4-(4-octyl-1H-1,2,3-triazol-1-yl)phenyl]ethanol
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3-(((4-((4-(4-chlorophenyl)pyrimidin-2-yl)amino)phenyl)amino)methyl)-6,7-dimethoxyquinolin-2(1H)-one
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3-((4-(4-chlorophenyl)pyrimidin-2-yl)-1-yl)oxymethyl)quinolin-2(1H)-one
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3-O-sulfogalactosylceramide
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endogenous glycolipid sulfatide, binds to and inhibits the activity of isoform Sphk2 and the closely related ceramide kinase Cerk, but not isoform Sphk1. The lipid binding domain is mapped to the N-terminus of Sphk2, residues 1-175, a region of sequence that is absent in Sphk1, but aligns with a pleckstrin homology domain in Cerk
3-[4-(4-octylphenyl)-1H-1,2,3-triazol-1-yl]pyridine
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4-((4-(4-chlorophenyl)pyrimidin-2-yl)amino)phenol
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4-(4-(4-chloro-phenyl)thiazol-2-ylamino)phenol
4-(4-octyl-1H-1,2,3-triazol-1-yl)phenol
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4-azido-1-(4-methylphenethyl)piperidine
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4-azido-1-(4-octylphenethyl)piperidine
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4-fluoro-1-[2-(4-octylphenyl)ethyl]piperidine
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4-methoxy-1-[2-(4-octylphenyl)ethyl]piperidine
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4-octyl-N-(pyridin-4-ylmethyl)benzamide
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4-[5-[(1S)-6-hydroperoxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl]-6-hydroxy-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl]benzoic acid
i.e. ZINC16995081
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5-(4-chlorophenyl)-N-(pyridin-4-ylmethyl)tricyclo[3.3.1.13,7]decane-2-carboxamide
selective inhibition of isoform SK2
5-(4-chlorophenyl)-N-[2-(3,4-dihydroxyphenyl)ethyl]tricyclo[3.3.1.13,7]decane-2-carboxamide
inhibits both isoforms SK1 and SK2; inhibits both isoforms SK1 and SK2
5-([(3S)-3-(2-hydroxyethyl)-4-[(6-methylpyridin-2-yl)methyl]piperazin-1-yl]methyl)-2-methoxyphenol
i.e. ZINC19792941
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5-[[2-(3-methylphenyl)hydrazinyl]methylidene]-2-thioxodihydropyrimidine-4,6(1H,5H)-dione
i.e. ZINC00221579
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6,7-dihydroxy-3-(((4-((4-(naphthalene-2-yl)pyrimidin-2-yl)amino)phenyl)amino)methyl)quinolin-2(1H)-one
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6,7-dimethoxy-3-(((4-((4-(naphthalen-2-yl)pyrimidin-2-yl)amino)phenyl)amino)methyl)quinolin-2(1H)-one
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6-hydroxy-5-[2-[(4-hydroxy-2-methyl-6-oxo-1,6-dihydropyrimidin-5-yl)methyl]pentyl]-2-methylpyrimidin-4(3H)-one
i.e. ZINC18996465
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6-methoxy-3-(((4-((4-(naphthalen-2-yl)pyrimidin-2-yl)amino)phenyl)amino)methyl)quinolin-2(1H)-one
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6-[5-[(2S)-1-carbamimidoylpyrrolidin-2-yl]-1,2,4-oxadiazol-3-yl]naphthalen-2-yl 4-methylbenzene-1-sulfonate
isoform SphK2 shows 89% residual activity at 0.001 mM
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7-(6-amino-9H-purin-9-yl)heptanoic acid
i.e. ZINC01569549
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ABC294640
Amgen 23
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Amgen 82
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Amgen-82
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amino((1S,3S)-3-hydroxy-2-(3-(4-octylphenyl)-1,2,4-oxadiazol-5-yl)pyrrolidin-1-yl)methaniminium
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amino((1S,4S)-4-hydroxy-2-(3-(4-octylphenyl)-1,2,4-oxadiazol-5-yl)pyrrolidin-1-yl)methaniminium
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amino((2S,4R)-4-hydroxy-2-(3-(4-octylphenyl)-1,2,4-oxadiazol-5-yl)pyrrolidin-1-yl)methaniminium
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amino(3-(3-(4-octylphenyl)-1,2,4-oxadiazol-5-yl)azetidin-1-yl)methaniminium
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B-5354c
BML-258
74.5% inhibition at 0.05 mM
Bodipy-sphingosine conjugate
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bovine serum albumin
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camptothecin
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CB5468139
potent and selective isoform SphK1 inhibitor
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Cutsum
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detergent, required for sphinganine suspension, 0.05 mg/ml gives optimal rates, inhibition above 1 mg/ml
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D(+)threo-Sphinganine
D,L-threo-dihydrosphingosine
dihydrosphingosine
dimethylsphingosine
DL-threo-dihydrosphinganine
competitive inhibitor
DL-threo-dihydrosphingosine
docetaxel
erythro-dihydrosphingosine
F-12509A
fingolimod
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FTY720
galactosylceramide
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0.01 mM, isoform SphK2, 84% of initial activity, isoform SphK1, 109% of initial activity
galactosylceramide 3-sulphate
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0.01 mM, isoform SphK2, 37% of initial activity, isoform SphK1, 156% of initial activity
Genzyme-51
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K145
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L(-)erythro-Sphinganine
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L(-)threo-Sphinganine
L-erythro-sphingosine
0.005 mM, 41% inhibition; 0.005 mM, 43% inhibition
Melatonin
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melatonin decreases enzymic activity in PC-3 cells during hypoxia. In addition, Melatonin inhibits the stability of hypoxia inducible factor 1alpha in a time- and concentration-dependent manner and suppresses AKT/glycogen synthase kinase-3beta signaling pathway
MP-A08
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N,N,N-trimethylsphingosine
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N,N-dimethyl sphingosine
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N,N-dimethyl-4-(3-octylphenyl)-N-propylcyclohexan-1-aminium
potent and selective isoform SphK2 inhibitor
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N,N-dimethylsphingosine
N-((2S,3S)-1,3-dihydroxy-4-phenylbutan-2-yl)tridecanamide
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i.e. N-((2S,3S)-1,3-dihydroxy-4-phenylbutan-2-yl)tridecanamide, synthetic sphingosine analogue, specific inhibition of isozymes SphK1 and SphK2
N-(1-carbamimidoylcyclopropyl)-3-dodecylbenzamide
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N-(1-carbamimidoylcyclopropyl)-4-dodecylbenzamide
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N-(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-N-cyclohexylacetamide
selective inhibition of isoform SK1
N-(4-hydroxyphenyl)-4-octylbenzamide
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N-cyclohexyl-N-(3-hydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)acetamide
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N-ethylmaleimide
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N-[(1R)-1-(hydroxymethyl)-3-phenylpropyl]tridecanamide
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i.e. N-((R)-1-hydroxy-4-phenylbutan-2-yl)tridecanamide, synthetic sphingosine analogue, specific inhibition of isozymes SphK1 and SphK2
N-[(1R)-3-phenyl-1-(pyrrolidin-1-ylmethyl)propyl]decanamide
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i.e. N-((R)-4-phenyl-1-(pyrrolidin-1-yl)butan-2-yl)decanamide, synthetic sphingosine analogue, specific inhibition of isozymes SphK1 and SphK2
N-[(1S)-1-methyl-3-phenylpropyl]hexadecanamide
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i.e. N-((R)-1-hydroxy-4-phenylbutan-2-yl)palmitamide, synthetic sphingosine analogue, specific inhibition of isozymes SphK1 and SphK2
N-[(1S,2R)-2-hydroxy-1-(hydroxymethyl)-3-phenylpropyl]hexadecanamide
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i.e. N-((2S,3R)-1,3-dihydroxy-4-phenylbutan-2-yl)palmitamide, synthetic sphingosine analogue, specific inhibition of isozymes SphK1 and SphK2
N-[(1S,2R)-2-hydroxy-1-(hydroxymethyl)-3-phenylpropyl]tridecanamide
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i.e. N-((2S,3R)-1,3-dihydroxy-4-phenylbutan-2-yl)tridecanamide, synthetic sphingosine analogue, specific inhibition of isozymes SphK1 and SphK2
N-[(1S,2R)-2-hydroxy-3-phenyl-1-(pyrrolidin-1-ylmethyl)propyl]octadecanamide
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i.e. N-((2S,3R)-3-hydroxy-4-phenyl-1-(pyrrolidin-1-yl)butan-2-yl)stearamide, synthetic sphingosine analogue, specific inhibition of isozymes SphK1 and SphK2
N-[(1S,2S)-2-hydroxy-1-(hydroxymethyl)-3-phenylpropyl]hexadecanamide
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i.e. N-((2S,3S)-1,3-dihydroxy-4-phenylbutan-2-yl)palmitamide, synthetic sphingosine analogue, specific inhibition of isozymes SphK1 and SphK2
N-[(1S,2S)-2-hydroxy-1-(morpholin-4-ylmethyl)-3-phenylpropyl]decanamide
-
i.e. N-((2S,3S)-3-hydroxy-1-morpholino-4-phenylbutan-2-yl)decanamide, synthetic sphingosine analogue, specific inhibition of isozymes SphK1 and SphK2
N-[(1S,2S)-2-hydroxy-3-phenyl-1-(pyrrolidin-1-ylmethyl)propyl]decanamide
-
i.e. N-((2S,3S)-3-hydroxy-4-phenyl-1-(pyrrolidin-1-yl)butan-2-yl)decanamide, synthetic sphingosine analogue, specific inhibition of isozymes SphK1 and SphK2
N-[(1S,2S)-2-hydroxy-3-phenyl-1-(pyrrolidin-1-ylmethyl)propyl]octadecanamide
-
i.e. N-((2S,3S)-3-hydroxy-4-phenyl-1-(pyrrolidin-1-yl)butan-2-yl)stearamide, synthetic sphingosine analogue, specific inhibition of isozymes SphK1 and SphK2
N-[(2S)-1-amino-1-iminopropan-2-yl]-3-octylbenzamide
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N-[4-(2-hydroxyethyl)phenyl]-4-octylbenzamide
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p-chloromercuribenzoate
-
-
PF-543
phosphatidylinositol 4,5-bisphosphate
-
0.01 mM, isoform SphK2, 60% of initial activity, isoform SphK1, 90% of initial activity
phosphatidylinositol 4-phosphate
-
0.01 mM, isoform SphK2, 89% of initial activity, isoform SphK1, 175% of initial activity
phytosphingosine
0.0025 mM, 21% inhibition; 0.0025 mM, 64% inhibition
SG-12
i.e. (2S,3R)-2-amino-4-(4-octylphenyl)butane-1,3-diol, potent and selective isoform SphK2 inhibitor
-
siponimod
-
-
SKI-II
SLC5081308
-
SLC5091592
-
SLC5111312
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SLM6031434
the inhibitor is 23fold selective for isoform SphK2 over SphK1 with 51% inhibition of isoform SphK2 at 0.0003 mM
-
SLM6071469
i.e. (S)-2-(3-(3-(trifluoromethyl)-4-((4-(trifluoromethyl)-benzyl)oxy)phenyl)-1,2,4-oxadiazol-5-yl)pyrrolidine-1-carboximidamide. The inhibitor is 73fold selective for isoform SphK2 over SphK1 with 65% inhibition of isoform SphK2 at 0.0003 mM
-
SLP-120701
potent and selective isoform SphK2 inhibitor
-
SLP7111228
-
SLR080811
sphingosine kinase inhibitor
-
can influence co-stimulatory molecules (CD40, CD80, CD86 and MHC class II) and cytokine production (IL-12 and IL-10) in murine bone marrow-derived dendritic cells. Sphingosine kinase inhibitor significantly inhibits co-stimulatory molecules in dendritic cells. Sphingosine kinase inhibitor suppresses IL-12 production by dendritic cells and IFN-gamma production by T cells
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sphingosine kinase inhibitor II
-
-
-
Triton X-100
[(2R)-1-([4-[(3-cyclohexylphenoxy)methyl]phenyl]methyl)pyrrolidin-2-yl]methanol
-
[(2R)-1-[2-(4-dodecylphenyl)ethyl]pyrrolidin-2-yl]methanol
-
[(2R)-1-[2-(4-methylphenyl)ethyl]pyrrolidin-2-yl]methanol
-
[(2R)-1-[2-(4-octylphenyl)ethyl]pyrrolidin-2-yl]methanol
-
[(2S)-1-[2-(4-dodecylphenyl)ethyl]pyrrolidin-2-yl]methanol
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[(2S)-1-[2-(4-octylphenyl)ethyl]pyrrolidin-2-yl]methanol
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additional information
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