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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

Activating Compound

Activating Compound on EC 2.7.1.91 - sphingosine kinase

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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(2S)-2-(3-[6-[(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)methoxy]naphthalen-2-yl]-1,2,4-oxadiazol-5-yl)pyrrolidine-1-carboximidamide
isoform SphK2 shows 104% activity at 0.001 mM
-
(2S)-2-[3-(6-hydroxynaphthalen-2-yl)-1,2,4-oxadiazol-5-yl]pyrrolidine-1-carboximidamide
isoform SphK2 shows 106% activity 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 118% activity at 0.001 mM
-
(2S)-2-[3-[6-(2-oxo-2-phenylethoxy)naphthalen-2-yl]-1,2,4-oxadiazol-5-yl]pyrrolidine-1-carboximidamide
isoform SphK2 shows 103% activity at 0.001 mM
-
(2S)-2-[3-[6-(3-methoxypropoxy)naphthalen-2-yl]-1,2,4-oxadiazol-5-yl]pyrrolidine-1-carboximidamide
isoform SphK2 shows 109% activity at 0.001 mM
-
(4-hydroxypiperidin-1-yl)(4-octylphenyl)methanone
-
11,12-epoxy-(5Z,8Z,14Z)-eicosatrienoic acid
-
treatment markedly augments SK activity in HUVECs. At the concentration of 1 mM, 11,12-epoxy-(5Z,8Z,14Z)-eicosatrienoic acid increases SK activity by 110% and the maximal effect on SK activation is observed at 20 min after 11,12-epoxy-(5Z,8Z,14Z)-eicosatrienoic acid addition. Inhibition of SK by a specific inhibitor, SKI-II, markedly attenuates 11,12-epoxy-(5Z,8Z,14Z)-eicosatrienoic acid-induced endothelial cell proliferation. 11,12-Epoxy-(5Z,8Z,14Z)-eicosatrienoic acid-induced activation of Akt kinase and transactivation of the epidermal growth factor receptor are also inhibited by SKI-II
12-O-tetradecanoylphorbol-13-acetate
50 nM, maximum increase in activity after 24 h
2-[4-(4-octyl-1H-1,2,3-triazol-1-yl)phenyl]ethanol
-
4-(4-octyl-1H-1,2,3-triazol-1-yl)phenol
-
4-octyl-N-(pyridin-4-ylmethyl)benzamide
-
bovine serum albumin
-
the enzyme activity is higher with substrate solubilized by bovine serum albumin compared to Triton X-100
-
Calmodulin
Ca2+-dependent binding of recombinant wild-type and mutant enzymes
camptothecin
0.003 mM camptothecin induces marked elevation of SPHK activity, reaching a maximal level with approximately 250% of the control untreated cells at 36 h
ceramide 1-phosphate
-
cholesterol
-
0.01 mM, isoform SphK2, 107% of initial activity
Cutsum
-
detergent, required for sphinganine suspension, 0.05 mg/ml gives optimal rates, inhibition above 1 mg/ml
-
endothelin-1
1 nM, 2.4fold and 2.7fold increase of activity after 5 and 10 min, respectively
G-protein-coupled receptor agonists
-
-
-
galactosylceramide
-
0.01 mM, isoform SphK2, 84% of initial activity, isoform SphK1, 109% of initial activity
galactosylceramide 3-sulfate
-
0.01 mM, isoform SphK2, 37% of initial activity, isoform SphK1, 156% of initial activity
growth factors
-
platelet- and nerve-derived growth factors
-
heregulin
-
heregulin stimulates SphK1 activity only in filamin A-expressing A7 melanoma cells but not in filamin A-deficient cells and induces its translocation and colocalization with filamin A at lamellipodia. SphK1 is required for heregulin-induced migration, lamellipodia formation, activation of PAK1, and subsequent filamin A phosphorylation. Sphingosine 1-phosphate directly stimulates PAK1 kinase. Heregulin also induces colocalization of S1P1, the promotility sphingosine 1-phosphate receptor, but not S1P2, with SphK1 and filamin A at membrane ruffles
-
histamine
0.001 mM, up to 5fold increase of activity after 20 h
immunoglobulins E and G
-
-
-
jasplakinolide
latrunculin B
lipopolysaccharide
-
increases Sk1 transcription which is accompanied by increased SK activity and generation of sphingosine 1-phosphate. Sphingosine 1-phosphate is able to cause increases in COX-2 and PGE2 levels in RAW cells
muscarinic acetylcholine agonists
-
-
-
N,N-dimethylsphingosine
0.005 mM, activation to 106% of control
N-(1,3-dihydroxyisopropyl)-2-hexyl-3-oxo-decanamide
N-(4-hydroxyphenyl)-4-octylbenzamide
-
phorbol 12-myristate 13-acetate
-
phosphatidic acid
phosphatidylinositol
phosphatidylinositol 4-phosphate
-
0.01 mM, isoform SphK2, 89% of initial activity, isoform SphK1, 175% of initial activity
phosphatidylinositol bisphosphate
-
phosphatidylserine
sphingosine 1-phosphate
-
-
thrombin
-
stimulation of the lung epithelial cell line A-549 by thrombin leads to transient increase of SPHK1 activity and elevation of intracellular sphingosine 1-phosphate, abrogation of this stimulation by SPHK1-specific siRNA, pharmacological inhibition, or expression of a dominant-negative SPHK1 mutant blocks the response to thrombin. PAR-1 or thrombin-induced cytokine production and adhesion factor expression of human umbilical vein endothelial cells is also dependent on SPHK1
-
TNF-alpha
-
transforming growth factor beta1
5ng/ml
-
Triton X-100
tumor necrosis factor-alpha
-
additional information
-