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Literature summary extracted from

  • Tangadanchu, V.K.R.; Jiang, H.; Yu, Y.; Graham, T.J.A.; Liu, H.; Rogers, B.E.; Gropler, R.; Perlmutter, J.; Tu, Z.
    Structure-activity relationship studies and bioactivity evaluation of 1,2,3-triazole containing analogues as a selective sphingosine kinase-2 inhibitors (2020), Eur. J. Med. Chem., 206, 112713 .
    View publication on PubMed

Inhibitors

EC Number Inhibitors Comment Organism Structure
2.7.1.91 (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 Homo sapiens
2.7.1.91 (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 Homo sapiens
2.7.1.91 (5Z)-3-(2-aminoethyl)-5-[3-(4-butoxyphenyl)propylidene]-1,3-thiazolidine-2,4-dione potent and selective isoform SphK2 inhibitor Homo sapiens
2.7.1.91 (R)-FTY720-OMe potent and selective isoform SphK2 inhibitor Homo sapiens
2.7.1.91 (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
-
 Homo sapiens
2.7.1.91 (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
-
 Homo sapiens
2.7.1.91 (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
-
 Homo sapiens
2.7.1.91 (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
-
 Homo sapiens
2.7.1.91 (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
-
 Homo sapiens
2.7.1.91 (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
-
 Homo sapiens
2.7.1.91 (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
-
 Homo sapiens
2.7.1.91 (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
-
 Homo sapiens
2.7.1.91 (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
-
 Homo sapiens
2.7.1.91 (S)-2-((3-(4-((4-butyl-1H-1,2,3-triazol-1-yl)methyl)phenyl)-1,2,4-oxadiazol-5-yl)pyrrolidine-1-carboximidamide
-
 Homo sapiens
2.7.1.91 (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
-
 Homo sapiens
2.7.1.91 (S)-2-((3-(4-((4-cyclopropyl-1H-1,2,3-triazol-1-yl)methyl)phenyl)-1,2,4-oxadiazol-5-yl)pyrrolidine-1-carboximidamide
-
 Homo sapiens
2.7.1.91 (S)-2-((3-(4-((4-phenyl-1H-1,2,3-triazol-1-yl)methyl)phenyl)-1,2,4-oxadiazol-5-yl)pyrrolidine-1-carboximidamide
-
 Homo sapiens
2.7.1.91 (S)-2-((3-(4-((4-phenyl-1H-1,2,3-triazol-1-yl)methyl)phenyl)-1,2,4-oxadiazol-5yl)methyl)pyrrolidine-1-carboximidamide
-
 Homo sapiens
2.7.1.91 (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
-
 Homo sapiens
2.7.1.91 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
-
 Homo sapiens
2.7.1.91 1-(3-(4-((4-cyclopropyl-1H-1,2,3-triazol-1-yl)methyl)phenyl)-1,2,4-oxadiazol-5-yl)cyclopropanecarboximidamide
-
 Homo sapiens
2.7.1.91 1-(3-(4-((4-phenyl-1H-1,2,3-triazol-1-yl)methyl)phenyl)-1,2,4-oxadiazol-5-yl)cyclopropanecarboximidamide
-
 Homo sapiens
2.7.1.91 ABC294640 potent and selective isoform SphK2 inhibitor Homo sapiens
2.7.1.91 Amgen 23 potent and selective isoform SphK1 inhibitor Homo sapiens
2.7.1.91 CB5468139 potent and selective isoform SphK1 inhibitor Homo sapiens
2.7.1.91 K145 i.e. (5E)-3-(2-aminoethyl)-5-[3-(4-butoxyphenyl)propylidene]-1,3-thiazolidine-2,4-dione, potent and selective isoform SphK2 inhibitor Homo sapiens
2.7.1.91 MP-A08
-
 Homo sapiens
2.7.1.91 N,N-dimethyl-4-(3-octylphenyl)-N-propylcyclohexan-1-aminium potent and selective isoform SphK2 inhibitor Homo sapiens
2.7.1.91 PF-543 potent and selective isoform SphK1 inhibitor Homo sapiens
2.7.1.91 SG-12 i.e. (2S,3R)-2-amino-4-(4-octylphenyl)butane-1,3-diol, potent and selective isoform SphK2 inhibitor Homo sapiens
2.7.1.91 SLP-120701 potent and selective isoform SphK2 inhibitor Homo sapiens
2.7.1.91 SLP7111228 potent and selective isoform SphK1 inhibitor Homo sapiens
2.7.1.91 [(2R)-1-([4-[(3-cyclohexylphenoxy)methyl]phenyl]methyl)pyrrolidin-2-yl]methanol
-
 Homo sapiens

Metals/Ions

EC Number Metals/Ions Comment Organism Structure
2.7.1.91 Mg2+ 20 mM used in assay conditions Homo sapiens

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
2.7.1.91 ATP + sphingosine Homo sapiens
-
 ADP + sphingosine 1-phosphate
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
2.7.1.91 Homo sapiens Q9NRA0
-
-
2.7.1.91 Homo sapiens Q9NYA1
-
-

Source Tissue

EC Number Source Tissue Comment Organism Textmining
2.7.1.91 U-251MG cell
-
 Homo sapiens
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
2.7.1.91 ATP + sphingosine
-
 Homo sapiens ADP + sphingosine 1-phosphate
-
 ?

Synonyms

EC Number Synonyms Comment Organism
2.7.1.91 sphingosine kinase-1
-
 Homo sapiens
2.7.1.91 sphingosine kinase-2
-
 Homo sapiens
2.7.1.91 SPHK1 isoform Homo sapiens
2.7.1.91 SPHK2 isoform Homo sapiens

Ki Value [mM]

EC Number Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
2.7.1.91 0.000089
-
 (2S)-2-[3-[3-(trifluoromethyl)-4-[[4-(trifluoromethyl)phenyl]methoxy]phenyl]-1,2,4-oxadiazol-5-yl]pyrrolidine-1-carboximidamide isoform SphK2, at pH 8.0 and 25°C Homo sapiens
2.7.1.91 0.00009
-
 (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 isoform SphK2, at pH 8.0 and 25°C Homo sapiens
2.7.1.91 0.00012
-
 (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 isoform SphK1, at pH 8.0 and 25°C Homo sapiens
2.7.1.91 0.0064
-
 (5Z)-3-(2-aminoethyl)-5-[3-(4-butoxyphenyl)propylidene]-1,3-thiazolidine-2,4-dione isoform SphK2, at pH 8.0 and 25°C Homo sapiens
2.7.1.91 0.0065
-
 (2S)-2-[3-[3-(trifluoromethyl)-4-[[4-(trifluoromethyl)phenyl]methoxy]phenyl]-1,2,4-oxadiazol-5-yl]pyrrolidine-1-carboximidamide isoform SphK1, at pH 8.0 and 25°C Homo sapiens
2.7.1.91 0.008
-
 N,N-dimethyl-4-(3-octylphenyl)-N-propylcyclohexan-1-aminium isoform SphK2, at pH 8.0 and 25°C Homo sapiens
2.7.1.91 0.016
-
 SLP-120701 IC50 above 100 mM, isoform SphK2, at pH 8.0 and 25°C Homo sapiens
2.7.1.91 0.06
-
 N,N-dimethyl-4-(3-octylphenyl)-N-propylcyclohexan-1-aminium isoform SphK1, at pH 8.0 and 25°C Homo sapiens

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
2.7.1.91 0.0000017
-
 IC50 below 0.0000017 mM, isoform SphK1, at pH 8.0 and 25°C Homo sapiens [(2R)-1-([4-[(3-cyclohexylphenoxy)methyl]phenyl]methyl)pyrrolidin-2-yl]methanol
2.7.1.91 0.0000017
-
 IC50 below 0.0000017 mM, isoform SphK2, at pH 8.0 and 25°C Homo sapiens [(2R)-1-([4-[(3-cyclohexylphenoxy)methyl]phenyl]methyl)pyrrolidin-2-yl]methanol
2.7.1.91 0.0000036
-
 isoform SphK1, at pH 8.0 and 25°C Homo sapiens PF-543
2.7.1.91 0.00002
-
 isoform SphK1, at pH 8.0 and 25°C Homo sapiens Amgen 23
2.7.1.91 0.000048
-
 isoform SphK1, at pH 8.0 and 25°C Homo sapiens SLP7111228
2.7.1.91 0.00016
-
 isoform SphK2, at pH 8.0 and 25°C Homo sapiens Amgen 23
2.7.1.91 0.000234
-
 isoform SphK2, at pH 8.0 and 25°C Homo sapiens (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
2.7.1.91 0.000248
-
 isoform SphK2, at pH 8.0 and 25°C Homo sapiens (S)-2-((3-(4-((4-cyclopropyl-1H-1,2,3-triazol-1-yl)methyl)phenyl)-1,2,4-oxadiazol-5-yl)pyrrolidine-1-carboximidamide
2.7.1.91 0.000254
-
 isoform SphK2, at pH 8.0 and 25°C Homo sapiens (S)-2-((3-(4-((4-butyl-1H-1,2,3-triazol-1-yl)methyl)phenyl)-1,2,4-oxadiazol-5-yl)pyrrolidine-1-carboximidamide
2.7.1.91 0.000261
-
 isoform SphK2, at pH 8.0 and 25°C Homo sapiens 1-(3-(4-((4-phenyl-1H-1,2,3-triazol-1-yl)methyl)phenyl)-1,2,4-oxadiazol-5-yl)cyclopropanecarboximidamide
2.7.1.91 0.000266
-
 isoform SphK2, at pH 8.0 and 25°C Homo sapiens (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
2.7.1.91 0.000269
-
 isoform SphK2, at pH 8.0 and 25°C Homo sapiens 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
2.7.1.91 0.00028
-
 isoform SphK2, at pH 8.0 and 25°C Homo sapiens (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
2.7.1.91 0.000359
-
 isoform SphK2, at pH 8.0 and 25°C Homo sapiens (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
2.7.1.91 0.000391
-
 isoform SphK2, at pH 8.0 and 25°C Homo sapiens (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
2.7.1.91 0.000396
-
 isoform SphK2, at pH 8.0 and 25°C Homo sapiens (S)-2-((3-(4-((4-phenyl-1H-1,2,3-triazol-1-yl)methyl)phenyl)-1,2,4-oxadiazol-5yl)methyl)pyrrolidine-1-carboximidamide
2.7.1.91 0.000452
-
 isoform SphK2, at pH 8.0 and 25°C Homo sapiens (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
2.7.1.91 0.00064
-
 isoform SphK2, at pH 8.0 and 25°C Homo sapiens (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
2.7.1.91 0.000687
-
 isoform SphK2, at pH 8.0 and 25°C Homo sapiens (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
2.7.1.91 0.000717
-
 isoform SphK2, at pH 8.0 and 25°C Homo sapiens 1-(3-(4-((4-cyclopropyl-1H-1,2,3-triazol-1-yl)methyl)phenyl)-1,2,4-oxadiazol-5-yl)cyclopropanecarboximidamide
2.7.1.91 0.000909
-
 isoform SphK2, at pH 8.0 and 25°C Homo sapiens (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
2.7.1.91 0.002
-
 IC50 above 0.01 mM, isoform SphK1, at pH 8.0 and 25°C Homo sapiens CB5468139
2.7.1.91 0.0064
-
 isoform SphK2, at pH 8.0 and 25°C Homo sapiens K145
2.7.1.91 0.0069
-
 isoform SphK2, at pH 8.0 and 25°C Homo sapiens MP-A08
2.7.1.91 0.0098
-
 isoform SphK2, at pH 8.0 and 25°C Homo sapiens ABC294640
2.7.1.91 0.01
-
 IC50 above 0.01 mM, isoform SphK2, at pH 8.0 and 25°C Homo sapiens SLP7111228
2.7.1.91 0.0165
-
 isoform SphK2, at pH 8.0 and 25°C Homo sapiens (R)-FTY720-OMe
2.7.1.91 0.022
-
 isoform SphK2, at pH 8.0 and 25°C Homo sapiens SG-12
2.7.1.91 0.027
-
 isoform SphK1, at pH 8.0 and 25°C Homo sapiens MP-A08
2.7.1.91 100
-
 IC50 above 100 mM, isoform SphK2, at pH 8.0 and 25°C Homo sapiens CB5468139