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Literature summary for 2.7.1.91 extracted from

  • Congdon, M.D.; Kharel, Y.; Brown, A.M.; Lewis, S.N.; Bevan, D.R.; Lynch, K.R.; Santos, W.L.
    Structure-activity relationship studies and molecular modeling of naphthalene-based sphingosine kinase 2 inhibitors (2016), ACS Med. Chem. Lett., 7, 229-234 .
    View publication on PubMedView publication on EuropePMC
Search for more literature for 2.7.1.91

Activating Compound

Activating Compound Comment Organism Structure
(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 Homo sapiens
(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 Homo sapiens
(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 Homo sapiens
(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 Homo sapiens
(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 Homo sapiens

Inhibitors

Inhibitors Comment Organism Structure
(2R,4S)-2-(hydroxymethyl)-1-[2-[4-([4-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]amino)phenyl]ethyl]piperidin-4-ol
-
 Homo sapiens
(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 Homo sapiens
(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 Homo sapiens
(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 Homo sapiens
(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 Homo sapiens
(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 Homo sapiens
(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 Homo sapiens
(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 Homo sapiens
(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 Homo sapiens
(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 Homo sapiens
(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 Homo sapiens
(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 Homo sapiens
(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 Homo sapiens
(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 Homo sapiens
(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 Homo sapiens
(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 Homo sapiens
(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 Homo sapiens
(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 Homo sapiens
(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 Homo sapiens
(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 Homo sapiens
(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 Homo sapiens
(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 Homo sapiens
(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 Homo sapiens
(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 Homo sapiens
(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 Homo sapiens
(5Z)-3-(2-aminoethyl)-5-[3-(4-butoxyphenyl)propylidene]-1,3-thiazolidine-2,4-dione specific inhibitor for isoform SphK2 Homo sapiens
(R)-FTY720-OMe
-
 Homo sapiens
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 Homo sapiens
ABC294640 selective isoform SphK2 inhibitor Homo sapiens
Amgen 82
-
 Homo sapiens
K145 i.e. (5E)-3-(2-aminoethyl)-5-[3-(4-butoxyphenyl)propylidene]-1,3-thiazolidine-2,4-dione Homo sapiens
PF-543
-
 Homo sapiens
SLR080811 isoform SphK2 shows 61% residual activity at 0.01 mM Homo sapiens

Natural Substrates/ Products (Substrates)

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

Organism

Organism UniProt Comment Textmining
Homo sapiens Q9NRA0
-
-

Substrates and Products (Substrate)

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

Synonyms

Synonyms Comment Organism
sphingosine kinase 2
-
 Homo sapiens
SPHK2 isoform Homo sapiens

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
0.00002
-
 Amgen 82 isoform SphK2, pH and temperature not specified in the publication Homo sapiens
0.0009
-
 (2S,3S)-3-hydroxy-2-[3-[6-(pentyloxy)naphthalen-2-yl]-1,2,4-oxadiazol-5-yl]pyrrolidine-1-carboximidamide isoform SphK2, pH and temperature not specified in the publication Homo sapiens
0.00098
-
 (2S)-2-[3-[6-(pentyloxy)naphthalen-2-yl]-1,2,4-oxadiazol-5-yl]pyrrolidine-1-carboximidamide isoform SphK2, pH and temperature not specified in the publication Homo sapiens
0.00098
-
 (2S,3S)-3-hydroxy-2-[3-[6-(2-methylpropoxy)naphthalen-2-yl]-1,2,4-oxadiazol-5-yl]pyrrolidine-1-carboximidamide isoform SphK2, pH and temperature not specified in the publication Homo sapiens
0.00102
-
 (2S)-2-[3-[6-(hexyloxy)naphthalen-2-yl]-1,2,4-oxadiazol-5-yl]pyrrolidine-1-carboximidamide isoform SphK2, pH and temperature not specified in the publication Homo sapiens
0.0014
-
 SLR080811 isoform SphK2, pH and temperature not specified in the publication Homo sapiens
0.0038
-
 (2S)-2-[3-[6-(hexyloxy)naphthalen-2-yl]-1,2,4-oxadiazol-5-yl]pyrrolidine-1-carboximidamide isoform SphK2, pH and temperature not specified in the publication Homo sapiens
0.0064
-
 (5Z)-3-(2-aminoethyl)-5-[3-(4-butoxyphenyl)propylidene]-1,3-thiazolidine-2,4-dione isoform SphK2, pH and temperature not specified in the publication Homo sapiens

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.00002
-
 isoform SphK2, pH and temperature not specified in the publication Homo sapiens (2R,4S)-2-(hydroxymethyl)-1-[2-[4-([4-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]amino)phenyl]ethyl]piperidin-4-ol