BRENDA - Enzyme Database show

Identification of 2-mercaptohexanoic acids as dual inhibitors of 5-lipoxygenase and microsomal prostaglandin E2 synthase-1

Greiner, C.; Zettl, H.; Koeberle, A.; Pergola, C.; Northoff, H.; Schubert-Zsilavecz, M.; Werz, O.; Bioorg. Med. Chem. 19, 3394-3401 (2011)

Data extracted from this reference:

Inhibitors
EC Number
Inhibitors
Commentary
Organism
Structure
5.3.99.3
(2E)-2-[4-[3-(2,3-dimethylphenoxy)propoxy]benzylidene]hexanoic acid
28.3% residual activity at 0.01 mM
Homo sapiens
5.3.99.3
(2R)-2-([4-[3-(2,3-dimethylphenoxy)propoxy]phenyl]sulfanyl)hexanoic acid
-
Homo sapiens
5.3.99.3
(2S)-2-([4-[3-(2,3-dimethylphenoxy)propoxy]phenyl]sulfanyl)hexanoic acid
-
Homo sapiens
5.3.99.3
([4-[3-(2,3-dimethylphenoxy)propoxy]phenyl]sulfanyl)acetic acid
75.4% residual activity at 0.01 mM
Homo sapiens
5.3.99.3
2(4-(3-biphenyloxypropoxy)phenylthio)hexanoic acid
-
Homo sapiens
5.3.99.3
2-([4-[3-(2,3-dimethylphenoxy)propoxy]phenyl]sulfanyl)hexanoic acid
-
Homo sapiens
5.3.99.3
2-([4-[3-(2-methoxyphenoxy)propoxy]phenyl]sulfanyl)hexanoic acid
88.3% residual activity at 0.01 mM
Homo sapiens
5.3.99.3
2-([4-[3-(2-methylphenoxy)propoxy]phenyl]sulfanyl)hexanoic acid
-
Homo sapiens
5.3.99.3
2-([4-[3-(3-methoxyphenoxy)propoxy]phenyl]sulfanyl)hexanoic acid
59.1% residual activity at 0.01 mM
Homo sapiens
5.3.99.3
2-([4-[3-(3-methylphenoxy)propoxy]phenyl]sulfanyl)hexanoic acid
58% residual activity at 0.01 mM
Homo sapiens
5.3.99.3
2-([4-[3-(4-chloro-2-methoxyphenoxy)propoxy]phenyl]sulfanyl)hexanoic acid
-
Homo sapiens
5.3.99.3
2-([4-[3-(4-methylphenoxy)propoxy]phenyl]sulfanyl)hexanoic acid
-
Homo sapiens
5.3.99.3
2-([4-[3-(5,6,7,8-tetrahydronaphthalen-1-yloxy)propoxy]phenyl]sulfanyl)hexanoic acid
-
Homo sapiens
5.3.99.3
2-([4-[3-(quinolin-6-yloxy)propoxy]phenyl]sulfanyl)hexanoic acid
-
Homo sapiens
5.3.99.3
2-[(4-[3-[2-(propan-2-yl)phenoxy]propoxy]phenyl)sulfanyl]hexanoic acid
-
Homo sapiens
5.3.99.3
2-[(4-[3-[3-(propan-2-yl)phenoxy]propoxy]phenyl)sulfanyl]hexanoic acid
-
Homo sapiens
5.3.99.3
2-[(4-[3-[3-(trifluoromethyl)phenoxy]propoxy]phenyl)sulfanyl]hexanoic acid
-
Homo sapiens
5.3.99.3
2-[(4-[3-[4-chloro-3-(trifluoromethyl)phenoxy]propoxy]phenyl)sulfanyl]hexanoic acid
-
Homo sapiens
5.3.99.3
2-[4-[3-(2,3-dimethylphenoxy)propoxy]benzyl]hexanoic acid
-
Homo sapiens
5.3.99.3
2-[[4-(3-phenoxypropoxy)phenyl]sulfanyl]hexanoic acid
81.9% residual activity at 0.01 mM
Homo sapiens
5.3.99.3
3-[4-[3-(2,3-dimethylphenoxy)propoxy]phenyl]propanoic acid
83.9% residual activity at 0.01 mM
Homo sapiens
5.3.99.3
ethyl 2-([4-[3-(5,6,7,8-tetrahydronaphthalen-1-yloxy)propoxy]phenyl]sulfanyl)hexanoate
-
Homo sapiens
5.3.99.3
ethyl 2-([4-[3-(biphenyl-4-yloxy)propoxy]phenyl]sulfanyl)hexanoate
-
Homo sapiens
5.3.99.3
ethyl 2-([4-[3-(quinolin-6-yloxy)propoxy]phenyl]sulfanyl)hexanoate
83.9% residual activity at 0.01 mM
Homo sapiens
5.3.99.3
MK886
-
Homo sapiens
Organism
EC Number
Organism
Primary Accession No. (UniProt)
Commentary
Textmining
5.3.99.3
Homo sapiens
-
-
-
Source Tissue
EC Number
Source Tissue
Commentary
Organism
Textmining
5.3.99.3
A-549 cell
-
Homo sapiens
-
Substrates and Products (Substrate)
EC Number
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
5.3.99.3
Prostaglandin H2
-
714468
Homo sapiens
Prostaglandin E2
-
-
-
?
Cofactor
EC Number
Cofactor
Commentary
Organism
Structure
5.3.99.3
glutathione
-
Homo sapiens
IC50 Value
EC Number
IC50 Value
IC50 Value Maximum
Commentary
Organism
Inhibitor
Structure
5.3.99.3
0.0017
-
in 0.1 M potassium phosphate buffer, pH 7.4, at 4C
Homo sapiens
2-[(4-[3-[4-chloro-3-(trifluoromethyl)phenoxy]propoxy]phenyl)sulfanyl]hexanoic acid
5.3.99.3
0.002
-
in 0.1 M potassium phosphate buffer, pH 7.4, at 4C
Homo sapiens
2-[(4-[3-[3-(trifluoromethyl)phenoxy]propoxy]phenyl)sulfanyl]hexanoic acid
5.3.99.3
0.0022
-
in 0.1 M potassium phosphate buffer, pH 7.4, at 4C
Homo sapiens
2-([4-[3-(5,6,7,8-tetrahydronaphthalen-1-yloxy)propoxy]phenyl]sulfanyl)hexanoic acid
5.3.99.3
0.0022
-
in 0.1 M potassium phosphate buffer, pH 7.4, at 4C
Homo sapiens
2(4-(3-biphenyloxypropoxy)phenylthio)hexanoic acid
5.3.99.3
0.0024
-
in 0.1 M potassium phosphate buffer, pH 7.4, at 4C
Homo sapiens
MK886
5.3.99.3
0.0027
-
in 0.1 M potassium phosphate buffer, pH 7.4, at 4C
Homo sapiens
2-[(4-[3-[3-(propan-2-yl)phenoxy]propoxy]phenyl)sulfanyl]hexanoic acid
5.3.99.3
0.0029
-
in 0.1 M potassium phosphate buffer, pH 7.4, at 4C
Homo sapiens
2-([4-[3-(2,3-dimethylphenoxy)propoxy]phenyl]sulfanyl)hexanoic acid
5.3.99.3
0.0041
-
in 0.1 M potassium phosphate buffer, pH 7.4, at 4C
Homo sapiens
2-[(4-[3-[2-(propan-2-yl)phenoxy]propoxy]phenyl)sulfanyl]hexanoic acid
5.3.99.3
0.0042
-
in 0.1 M potassium phosphate buffer, pH 7.4, at 4C
Homo sapiens
(2R)-2-([4-[3-(2,3-dimethylphenoxy)propoxy]phenyl]sulfanyl)hexanoic acid
5.3.99.3
0.0046
-
in 0.1 M potassium phosphate buffer, pH 7.4, at 4C
Homo sapiens
(2S)-2-([4-[3-(2,3-dimethylphenoxy)propoxy]phenyl]sulfanyl)hexanoic acid
5.3.99.3
0.0071
-
in 0.1 M potassium phosphate buffer, pH 7.4, at 4C
Homo sapiens
2-[4-[3-(2,3-dimethylphenoxy)propoxy]benzyl]hexanoic acid
5.3.99.3
0.0088
-
in 0.1 M potassium phosphate buffer, pH 7.4, at 4C
Homo sapiens
2-([4-[3-(2-methylphenoxy)propoxy]phenyl]sulfanyl)hexanoic acid
5.3.99.3
0.0093
-
in 0.1 M potassium phosphate buffer, pH 7.4, at 4C
Homo sapiens
2-([4-[3-(4-methylphenoxy)propoxy]phenyl]sulfanyl)hexanoic acid
5.3.99.3
0.0094
-
in 0.1 M potassium phosphate buffer, pH 7.4, at 4C
Homo sapiens
2-([4-[3-(4-chloro-2-methoxyphenoxy)propoxy]phenyl]sulfanyl)hexanoic acid
5.3.99.3
0.01
-
IC50 above 0.01 mM, in 0.1 M potassium phosphate buffer, pH 7.4, at 4C
Homo sapiens
2-([4-[3-(2-methoxyphenoxy)propoxy]phenyl]sulfanyl)hexanoic acid
5.3.99.3
0.01
-
IC50 above 0.01 mM, in 0.1 M potassium phosphate buffer, pH 7.4, at 4C
Homo sapiens
2-([4-[3-(3-methoxyphenoxy)propoxy]phenyl]sulfanyl)hexanoic acid
5.3.99.3
0.01
-
IC50 above 0.01 mM, in 0.1 M potassium phosphate buffer, pH 7.4, at 4C
Homo sapiens
2-([4-[3-(3-methylphenoxy)propoxy]phenyl]sulfanyl)hexanoic acid
5.3.99.3
0.01
-
IC50 above 0.01 mM, in 0.1 M potassium phosphate buffer, pH 7.4, at 4C
Homo sapiens
2-[[4-(3-phenoxypropoxy)phenyl]sulfanyl]hexanoic acid
5.3.99.3
0.01
-
IC50 above 0.01 mM, in 0.1 M potassium phosphate buffer, pH 7.4, at 4C
Homo sapiens
2-([4-[3-(quinolin-6-yloxy)propoxy]phenyl]sulfanyl)hexanoic acid
5.3.99.3
0.01
-
IC50 above 0.01 mM, in 0.1 M potassium phosphate buffer, pH 7.4, at 4C
Homo sapiens
(2E)-2-[4-[3-(2,3-dimethylphenoxy)propoxy]benzylidene]hexanoic acid
5.3.99.3
0.01
-
IC50 above 0.01 mM, in 0.1 M potassium phosphate buffer, pH 7.4, at 4C
Homo sapiens
3-[4-[3-(2,3-dimethylphenoxy)propoxy]phenyl]propanoic acid
5.3.99.3
0.01
-
IC50 above 0.01 mM, in 0.1 M potassium phosphate buffer, pH 7.4, at 4C
Homo sapiens
([4-[3-(2,3-dimethylphenoxy)propoxy]phenyl]sulfanyl)acetic acid
5.3.99.3
0.01
-
IC50 above 0.01 mM, in 0.1 M potassium phosphate buffer, pH 7.4, at 4C
Homo sapiens
ethyl 2-([4-[3-(quinolin-6-yloxy)propoxy]phenyl]sulfanyl)hexanoate
Cofactor (protein specific)
EC Number
Cofactor
Commentary
Organism
Structure
5.3.99.3
glutathione
-
Homo sapiens
IC50 Value (protein specific)
EC Number
IC50 Value
IC50 Value Maximum
Commentary
Organism
Inhibitor
Structure
5.3.99.3
0.0017
-
in 0.1 M potassium phosphate buffer, pH 7.4, at 4C
Homo sapiens
2-[(4-[3-[4-chloro-3-(trifluoromethyl)phenoxy]propoxy]phenyl)sulfanyl]hexanoic acid
5.3.99.3
0.002
-
in 0.1 M potassium phosphate buffer, pH 7.4, at 4C
Homo sapiens
2-[(4-[3-[3-(trifluoromethyl)phenoxy]propoxy]phenyl)sulfanyl]hexanoic acid
5.3.99.3
0.0022
-
in 0.1 M potassium phosphate buffer, pH 7.4, at 4C
Homo sapiens
2-([4-[3-(5,6,7,8-tetrahydronaphthalen-1-yloxy)propoxy]phenyl]sulfanyl)hexanoic acid
5.3.99.3
0.0022
-
in 0.1 M potassium phosphate buffer, pH 7.4, at 4C
Homo sapiens
2(4-(3-biphenyloxypropoxy)phenylthio)hexanoic acid
5.3.99.3
0.0024
-
in 0.1 M potassium phosphate buffer, pH 7.4, at 4C
Homo sapiens
MK886
5.3.99.3
0.0027
-
in 0.1 M potassium phosphate buffer, pH 7.4, at 4C
Homo sapiens
2-[(4-[3-[3-(propan-2-yl)phenoxy]propoxy]phenyl)sulfanyl]hexanoic acid
5.3.99.3
0.0029
-
in 0.1 M potassium phosphate buffer, pH 7.4, at 4C
Homo sapiens
2-([4-[3-(2,3-dimethylphenoxy)propoxy]phenyl]sulfanyl)hexanoic acid
5.3.99.3
0.0041
-
in 0.1 M potassium phosphate buffer, pH 7.4, at 4C
Homo sapiens
2-[(4-[3-[2-(propan-2-yl)phenoxy]propoxy]phenyl)sulfanyl]hexanoic acid
5.3.99.3
0.0042
-
in 0.1 M potassium phosphate buffer, pH 7.4, at 4C
Homo sapiens
(2R)-2-([4-[3-(2,3-dimethylphenoxy)propoxy]phenyl]sulfanyl)hexanoic acid
5.3.99.3
0.0046
-
in 0.1 M potassium phosphate buffer, pH 7.4, at 4C
Homo sapiens
(2S)-2-([4-[3-(2,3-dimethylphenoxy)propoxy]phenyl]sulfanyl)hexanoic acid
5.3.99.3
0.0071
-
in 0.1 M potassium phosphate buffer, pH 7.4, at 4C
Homo sapiens
2-[4-[3-(2,3-dimethylphenoxy)propoxy]benzyl]hexanoic acid
5.3.99.3
0.0088
-
in 0.1 M potassium phosphate buffer, pH 7.4, at 4C
Homo sapiens
2-([4-[3-(2-methylphenoxy)propoxy]phenyl]sulfanyl)hexanoic acid
5.3.99.3
0.0093
-
in 0.1 M potassium phosphate buffer, pH 7.4, at 4C
Homo sapiens
2-([4-[3-(4-methylphenoxy)propoxy]phenyl]sulfanyl)hexanoic acid
5.3.99.3
0.0094
-
in 0.1 M potassium phosphate buffer, pH 7.4, at 4C
Homo sapiens
2-([4-[3-(4-chloro-2-methoxyphenoxy)propoxy]phenyl]sulfanyl)hexanoic acid
5.3.99.3
0.01
-
IC50 above 0.01 mM, in 0.1 M potassium phosphate buffer, pH 7.4, at 4C
Homo sapiens
2-([4-[3-(2-methoxyphenoxy)propoxy]phenyl]sulfanyl)hexanoic acid
5.3.99.3
0.01
-
IC50 above 0.01 mM, in 0.1 M potassium phosphate buffer, pH 7.4, at 4C
Homo sapiens
2-([4-[3-(3-methoxyphenoxy)propoxy]phenyl]sulfanyl)hexanoic acid
5.3.99.3
0.01
-
IC50 above 0.01 mM, in 0.1 M potassium phosphate buffer, pH 7.4, at 4C
Homo sapiens
2-([4-[3-(3-methylphenoxy)propoxy]phenyl]sulfanyl)hexanoic acid
5.3.99.3
0.01
-
IC50 above 0.01 mM, in 0.1 M potassium phosphate buffer, pH 7.4, at 4C
Homo sapiens
2-[[4-(3-phenoxypropoxy)phenyl]sulfanyl]hexanoic acid
5.3.99.3
0.01
-
IC50 above 0.01 mM, in 0.1 M potassium phosphate buffer, pH 7.4, at 4C
Homo sapiens
2-([4-[3-(quinolin-6-yloxy)propoxy]phenyl]sulfanyl)hexanoic acid
5.3.99.3
0.01
-
IC50 above 0.01 mM, in 0.1 M potassium phosphate buffer, pH 7.4, at 4C
Homo sapiens
(2E)-2-[4-[3-(2,3-dimethylphenoxy)propoxy]benzylidene]hexanoic acid
5.3.99.3
0.01
-
IC50 above 0.01 mM, in 0.1 M potassium phosphate buffer, pH 7.4, at 4C
Homo sapiens
3-[4-[3-(2,3-dimethylphenoxy)propoxy]phenyl]propanoic acid
5.3.99.3
0.01
-
IC50 above 0.01 mM, in 0.1 M potassium phosphate buffer, pH 7.4, at 4C
Homo sapiens
([4-[3-(2,3-dimethylphenoxy)propoxy]phenyl]sulfanyl)acetic acid
5.3.99.3
0.01
-
IC50 above 0.01 mM, in 0.1 M potassium phosphate buffer, pH 7.4, at 4C
Homo sapiens
ethyl 2-([4-[3-(quinolin-6-yloxy)propoxy]phenyl]sulfanyl)hexanoate
Inhibitors (protein specific)
EC Number
Inhibitors
Commentary
Organism
Structure
5.3.99.3
(2E)-2-[4-[3-(2,3-dimethylphenoxy)propoxy]benzylidene]hexanoic acid
28.3% residual activity at 0.01 mM
Homo sapiens
5.3.99.3
(2R)-2-([4-[3-(2,3-dimethylphenoxy)propoxy]phenyl]sulfanyl)hexanoic acid
-
Homo sapiens
5.3.99.3
(2S)-2-([4-[3-(2,3-dimethylphenoxy)propoxy]phenyl]sulfanyl)hexanoic acid
-
Homo sapiens
5.3.99.3
([4-[3-(2,3-dimethylphenoxy)propoxy]phenyl]sulfanyl)acetic acid
75.4% residual activity at 0.01 mM
Homo sapiens
5.3.99.3
2(4-(3-biphenyloxypropoxy)phenylthio)hexanoic acid
-
Homo sapiens
5.3.99.3
2-([4-[3-(2,3-dimethylphenoxy)propoxy]phenyl]sulfanyl)hexanoic acid
-
Homo sapiens
5.3.99.3
2-([4-[3-(2-methoxyphenoxy)propoxy]phenyl]sulfanyl)hexanoic acid
88.3% residual activity at 0.01 mM
Homo sapiens
5.3.99.3
2-([4-[3-(2-methylphenoxy)propoxy]phenyl]sulfanyl)hexanoic acid
-
Homo sapiens
5.3.99.3
2-([4-[3-(3-methoxyphenoxy)propoxy]phenyl]sulfanyl)hexanoic acid
59.1% residual activity at 0.01 mM
Homo sapiens
5.3.99.3
2-([4-[3-(3-methylphenoxy)propoxy]phenyl]sulfanyl)hexanoic acid
58% residual activity at 0.01 mM
Homo sapiens
5.3.99.3
2-([4-[3-(4-chloro-2-methoxyphenoxy)propoxy]phenyl]sulfanyl)hexanoic acid
-
Homo sapiens
5.3.99.3
2-([4-[3-(4-methylphenoxy)propoxy]phenyl]sulfanyl)hexanoic acid
-
Homo sapiens
5.3.99.3
2-([4-[3-(5,6,7,8-tetrahydronaphthalen-1-yloxy)propoxy]phenyl]sulfanyl)hexanoic acid
-
Homo sapiens
5.3.99.3
2-([4-[3-(quinolin-6-yloxy)propoxy]phenyl]sulfanyl)hexanoic acid
-
Homo sapiens
5.3.99.3
2-[(4-[3-[2-(propan-2-yl)phenoxy]propoxy]phenyl)sulfanyl]hexanoic acid
-
Homo sapiens
5.3.99.3
2-[(4-[3-[3-(propan-2-yl)phenoxy]propoxy]phenyl)sulfanyl]hexanoic acid
-
Homo sapiens
5.3.99.3
2-[(4-[3-[3-(trifluoromethyl)phenoxy]propoxy]phenyl)sulfanyl]hexanoic acid
-
Homo sapiens
5.3.99.3
2-[(4-[3-[4-chloro-3-(trifluoromethyl)phenoxy]propoxy]phenyl)sulfanyl]hexanoic acid
-
Homo sapiens
5.3.99.3
2-[4-[3-(2,3-dimethylphenoxy)propoxy]benzyl]hexanoic acid
-
Homo sapiens
5.3.99.3
2-[[4-(3-phenoxypropoxy)phenyl]sulfanyl]hexanoic acid
81.9% residual activity at 0.01 mM
Homo sapiens
5.3.99.3
3-[4-[3-(2,3-dimethylphenoxy)propoxy]phenyl]propanoic acid
83.9% residual activity at 0.01 mM
Homo sapiens
5.3.99.3
ethyl 2-([4-[3-(5,6,7,8-tetrahydronaphthalen-1-yloxy)propoxy]phenyl]sulfanyl)hexanoate
-
Homo sapiens
5.3.99.3
ethyl 2-([4-[3-(biphenyl-4-yloxy)propoxy]phenyl]sulfanyl)hexanoate
-
Homo sapiens
5.3.99.3
ethyl 2-([4-[3-(quinolin-6-yloxy)propoxy]phenyl]sulfanyl)hexanoate
83.9% residual activity at 0.01 mM
Homo sapiens
5.3.99.3
MK886
-
Homo sapiens
Source Tissue (protein specific)
EC Number
Source Tissue
Commentary
Organism
Textmining
5.3.99.3
A-549 cell
-
Homo sapiens
-
Substrates and Products (Substrate) (protein specific)
EC Number
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
5.3.99.3
Prostaglandin H2
-
714468
Homo sapiens
Prostaglandin E2
-
-
-
?
Expression
EC Number
Organism
Commentary
Expression
5.3.99.3
Homo sapiens
interleukin-1beta (1 ng/ml) induces mPGES-1 expression
up
Expression (protein specific)
EC Number
Organism
Commentary
Expression
5.3.99.3
Homo sapiens
interleukin-1beta (1 ng/ml) induces mPGES-1 expression
up