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Literature summary for 2.7.8.27 extracted from

  • Li, Y.L.; Qi, X.Y.; Jiang, H.; Deng, X.D.; Dong, Y.P.; Ding, T.B.; Zhou, L.; Men, P.; Chu, Y.; Wang, R.X.; Jiang, X.C.; Ye, D.Y.
    Discovery, synthesis and biological evaluation of 2-(4-(N-phenethylsulfamoyl)phenoxy)acetamides (SAPAs) as novel sphingomyelin synthase 1 inhibitors (2015), Bioorg. Med. Chem., 23, 6173-6184.
    View publication on PubMed
Search for more literature for 2.7.8.27

Application

Application Comment Organism
drug development enzyme SMS1 is a drug target for the treatment of atherosclerosis Homo sapiens

Cloned(Commentary)

Cloned (Comment) Organism
gene SGMS1, recombinnat overexpression of isozyme SMS1 in HeLa cells Homo sapiens

Inhibitors

Inhibitors Comment Organism Structure
2-(2-(benzyloxy)phenyl)-2-(phenylamino) acetonitrile
-
 Homo sapiens
2-(4-(N-phenethylsulfamoyl)phenoxy)-N-(2-(trifluoromethoxy)phenyl)acetamide
-
 Homo sapiens
2-(4-(N-phenethylsulfamoyl)phenoxy)-N-(o-tolyl)acetamide
-
 Homo sapiens
2-(4-(N-phenethylsulfamoyl)phenoxy)-N-phenylacetamide
-
 Homo sapiens
4-(2-((4-chlorobenzyl)amino)-2-oxoethoxy)-N-(pyridin-4-yl)benzamide
-
 Homo sapiens
4-(2-((4-chlorobenzyl)amino)-2-oxoethoxy)-N-phenethylbenzamide
-
 Homo sapiens
additional information structure-based virtual screening, synthesis and biological evaluation of 2-(4-(N-phenethylsulfamoyl)phenoxy)acetamides (SAPAs) as sphingomyelin synthase 1 inhibitors, molecular docking studies and interaction modes of SMS1 inhibitors with the active site of SMS1, overview Homo sapiens
N-(2-cyanophenyl)-2-(4-(N-phenethylsulfamoyl)phenoxy)acetamide
-
 Homo sapiens
N-(2-methoxyphenyl)-2-(4-(N-phenethylsulfamoyl)phenoxy)acetamide
-
 Homo sapiens
N-(2-nitrophenyl)-2-(4-(N-phenethylsulfamoyl)phenoxy)acetamide
-
 Homo sapiens
N-(3-fluorobenzyl)-2-(4-(N-phenethylsulfamoyl)phenoxy)acetamide
-
 Homo sapiens
N-(3-methoxyphenyl)-2-(4-(N-phenethylsulfamoyl)phenoxy)acetamide
-
 Homo sapiens
N-(4-bromobenzyl)-2-(4-(N-phenethylsulfamoyl)phenoxy)acetamide
-
 Homo sapiens
N-(4-chlorobenzyl)-2-(4-(N-(3-phenylpropyl)sulfamoyl)phenoxy)acetamide
-
 Homo sapiens
N-(4-chlorobenzyl)-2-(4-(N-(4-chlorobenzyl)sulfamoyl)phenoxy)acetamide
-
 Homo sapiens
N-(4-chlorobenzyl)-2-(4-(N-phenethylsulfamoyl)phenoxy)acetamide
-
 Homo sapiens
N-(4-chlorobenzyl)-2-(4-(N-phenylsulfamoyl)phenoxy)acetamide
-
 Homo sapiens
N-(4-chlorophenyl)-2-(4-(N-phenethylsulfamoyl)phenoxy)acetamide
-
 Homo sapiens
N-(4-fluoro-2-methoxyphenyl)-2-(4-(N-phenethylsulfamoyl)phenoxy)acetamide
-
 Homo sapiens
N-(4-fluorobenzyl)-2-(4-(N-phenethylsulfamoyl)phenoxy)acetamide
-
 Homo sapiens
N-(4-fluorophenyl)-2-(4-(N-phenethylsulfamoyl)phenoxy)acetamide
-
 Homo sapiens
N-(4-methoxybenzyl)-2-(4-(N-phenethylsulfamoyl)phenoxy)acetamide
-
 Homo sapiens
N-(4-methoxyphenyl)-2-(4-(N-phenethylsulfamoyl)phenoxy)acetamide
-
 Homo sapiens
N-benzyl-2-(4-(N-phenethylsulfamoyl)phenoxy)acetamide
-
 Homo sapiens
N-phenethyl-2-(4-(N-phenethylsulfamoyl)phenoxy)acetamide
-
 Homo sapiens
tricyclodecan-9-yl-xanthogenate
-
 Homo sapiens

Localization

Localization Comment Organism GeneOntology No. Textmining
trans-Golgi network
-
 Homo sapiens 5802
-

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
a ceramide + a phosphatidylcholine Homo sapiens
-
 a sphingomyelin + a 1,2-diacyl-sn-glycerol
-
 ?

Organism

Organism UniProt Comment Textmining
Homo sapiens Q86VZ5
-
-

Source Tissue

Source Tissue Comment Organism Textmining
macrophage SMS1 is the major SMS Homo sapiens
-
additional information SMS isoform SMS1 is expressed ubiquitously in all the tested tissues Homo sapiens
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
a ceramide + a phosphatidylcholine
-
 Homo sapiens a sphingomyelin + a 1,2-diacyl-sn-glycerol
-
 ?
a ceramide + a phosphatidylcholine substrate C6-NBD-ceramide, molecular docking studies and interaction modes of phosphatidylcholine with the active site of SMS1, overview Homo sapiens a sphingomyelin + a 1,2-diacyl-sn-glycerol detection and quantifcation of C6-NBD-sphingomyelin by HPLC using the reversed-phase C18 column and an isocratic elution with methanol/water/trifluoroacetic acid (89:11:0.1 (v/v)) ?

Synonyms

Synonyms Comment Organism
phosphatidylcholine:ceramide cholinephosphotransferase 1
-
 Homo sapiens
SGMS1
-
 Homo sapiens
SMS1
-
 Homo sapiens

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
37
-
 assay at Homo sapiens

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
7.4
-
 assay at Homo sapiens

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.0021
-
 pH 7.4, 37°C Homo sapiens N-(4-bromobenzyl)-2-(4-(N-phenethylsulfamoyl)phenoxy)acetamide
0.0052
-
 pH 7.4, 37°C Homo sapiens N-(4-chlorobenzyl)-2-(4-(N-phenethylsulfamoyl)phenoxy)acetamide
0.0059
-
 pH 7.4, 37°C Homo sapiens N-(4-methoxybenzyl)-2-(4-(N-phenethylsulfamoyl)phenoxy)acetamide
0.0066
-
 pH 7.4, 37°C Homo sapiens N-(4-chlorophenyl)-2-(4-(N-phenethylsulfamoyl)phenoxy)acetamide
0.0081
-
 pH 7.4, 37°C Homo sapiens N-(4-fluorobenzyl)-2-(4-(N-phenethylsulfamoyl)phenoxy)acetamide
0.0092
-
 pH 7.4, 37°C Homo sapiens N-(3-methoxyphenyl)-2-(4-(N-phenethylsulfamoyl)phenoxy)acetamide
0.0105
-
 pH 7.4, 37°C Homo sapiens N-(4-fluorophenyl)-2-(4-(N-phenethylsulfamoyl)phenoxy)acetamide
0.0142
-
 pH 7.4, 37°C Homo sapiens N-(2-methoxyphenyl)-2-(4-(N-phenethylsulfamoyl)phenoxy)acetamide
0.0147
-
 pH 7.4, 37°C Homo sapiens 2-(4-(N-phenethylsulfamoyl)phenoxy)-N-phenylacetamide
0.0156
-
 pH 7.4, 37°C Homo sapiens N-(3-fluorobenzyl)-2-(4-(N-phenethylsulfamoyl)phenoxy)acetamide
0.0231
-
 pH 7.4, 37°C Homo sapiens N-benzyl-2-(4-(N-phenethylsulfamoyl)phenoxy)acetamide
0.025
-
 pH 7.4, 37°C Homo sapiens 2-(2-(benzyloxy)phenyl)-2-(phenylamino) acetonitrile
0.05
-
 pH 7.4, 37°C Homo sapiens N-(4-chlorobenzyl)-2-(4-(N-(4-chlorobenzyl)sulfamoyl)phenoxy)acetamide
0.05
-
 pH 7.4, 37°C Homo sapiens N-phenethyl-2-(4-(N-phenethylsulfamoyl)phenoxy)acetamide
0.05
-
 pH 7.4, 37°C Homo sapiens N-(4-methoxyphenyl)-2-(4-(N-phenethylsulfamoyl)phenoxy)acetamide
0.1
-
 pH 7.4, 37°C Homo sapiens 4-(2-((4-chlorobenzyl)amino)-2-oxoethoxy)-N-phenethylbenzamide
0.1
-
 pH 7.4, 37°C Homo sapiens 4-(2-((4-chlorobenzyl)amino)-2-oxoethoxy)-N-(pyridin-4-yl)benzamide
0.1
-
 pH 7.4, 37°C Homo sapiens N-(4-chlorobenzyl)-2-(4-(N-(3-phenylpropyl)sulfamoyl)phenoxy)acetamide
0.1
-
 pH 7.4, 37°C Homo sapiens N-(4-chlorobenzyl)-2-(4-(N-phenylsulfamoyl)phenoxy)acetamide
0.1
-
 pH 7.4, 37°C Homo sapiens 2-(4-(N-phenethylsulfamoyl)phenoxy)-N-(o-tolyl)acetamide
0.1
-
 pH 7.4, 37°C Homo sapiens N-(2-nitrophenyl)-2-(4-(N-phenethylsulfamoyl)phenoxy)acetamide
0.1
-
 pH 7.4, 37°C Homo sapiens N-(2-cyanophenyl)-2-(4-(N-phenethylsulfamoyl)phenoxy)acetamide
0.1
-
 pH 7.4, 37°C Homo sapiens 2-(4-(N-phenethylsulfamoyl)phenoxy)-N-(2-(trifluoromethoxy)phenyl)acetamide
0.1
-
 pH 7.4, 37°C Homo sapiens N-(4-fluoro-2-methoxyphenyl)-2-(4-(N-phenethylsulfamoyl)phenoxy)acetamide
0.219
-
 pH 7.4, 37°C Homo sapiens tricyclodecan-9-yl-xanthogenate