BRENDA - Enzyme Database show

Pyrrole alkanoic acid derivatives as nuisance inhibitors of microsomal prostaglandin E2 synthase-1

Wiegard, A.; Hanekamp, W.; Griessbach, K.; Fabian, J.; Lehr, M.; Eur. J. Med. Chem. 48, 153-163 (2012)

Data extracted from this reference:

Inhibitors
EC Number
Inhibitors
Commentary
Organism
Structure
5.3.99.3
(1-benzyl-4-dodecanoyl-3,5-dimethyl-1H-pyrrol-2-yl)acetic acid
35% inhibition at 0.001 mM
Homo sapiens
5.3.99.3
(4-dodecanoyl-1,3,5-trimethyl-1H-pyrrol-2-yl)acetic acid
22% inhibition at 0.001 mM
Homo sapiens
5.3.99.3
(4-dodecanoyl-3,5-dimethyl-1H-pyrrol-2-yl)acetic acid
17% inhibition at 0.001 mM
Homo sapiens
5.3.99.3
1-benzyl-4-dodecanoyl-3,5-dimethyl-1H-pyrrole-2-carboxylic acid
65% inhibition at 0.001 mM
Homo sapiens
5.3.99.3
2-(4-dodecanoyl-3,5-dimethyl-1-phenylpyrrol-2-yl)acetic acid
23% inhibition at 0.001 mM
Homo sapiens
5.3.99.3
3-(1,3,5-trimethyl-4-octadecanoyl-1H-pyrrol-2-yl)propanoic acid
97% inhibition at 0.001 mM
Homo sapiens
5.3.99.3
3-(1,3,5-trimethyl-4-tetradecanoyl-1H-pyrrol-2-yl)propanoic acid
91% inhibition at 0.001 mM
Homo sapiens
5.3.99.3
3-(1-benzyl-4-dodecanoyl-3,5-dimethyl-1H-pyrrol-2-yl)propanoic acid
62% inhibition at 0.001 mM
Homo sapiens
5.3.99.3
3-(1-benzyl-4-dodecanoyl-5-methyl-3-phenylpyrrol-2-yl)propionic acid
64% inhibition at 0.001 mM
Homo sapiens
5.3.99.3
3-(4-dodecanoyl-1,3,5-trimethyl-1H-pyrrol-2-yl)propanoic acid
54% inhibition at 0.001 mM
Homo sapiens
5.3.99.3
3-(4-dodecanoyl-1,3,5-trimethylpyrrol-2-yl)-N-(benzenesulfonyl)propanamide
77% inhibition at 0.001 mM
Homo sapiens
5.3.99.3
3-(4-dodecanoyl-1,3,5-trimethylpyrrol-2-yl)-N-(methanesulfonyl)propanamide
52% inhibition at 0.001 mM
Homo sapiens
5.3.99.3
3-(4-dodecanoyl-1,3,5-trimethylpyrrol-2-yl)propanamide
39% inhibition at 0.001 mM
Homo sapiens
5.3.99.3
3-(4-dodecanoyl-1,3,5-trimethylpyrrol-2-yl)propanehydrazide
35% inhibition at 0.001 mM
Homo sapiens
5.3.99.3
3-(4-dodecanoyl-1,3,5-trimethylpyrrol-2-yl)propanenitrile
22% inhibition at 0.001 mM
Homo sapiens
5.3.99.3
3-(4-dodecanoyl-1,5-dimethyl-3-phenyl-1H-pyrrol-2-yl)propanoic acid
90% inhibition at 0.001 mM
Homo sapiens
5.3.99.3
3-(4-dodecanoyl-3,5-dimethyl-1-phenylpyrrol-2-yl)propionic acid
65% inhibition at 0.001 mM
Homo sapiens
5.3.99.3
3-(4-dodecanoyl-3,5-dimethyl-1H-pyrrol-2-yl)propanoic acid
38% inhibition at 0.001 mM
Homo sapiens
5.3.99.3
3-(4-hexadecanoyl-1,3,5-trimethyl-1H-pyrrol-2-yl)propanoic acid
97% inhibition at 0.001 mM
Homo sapiens
5.3.99.3
3-[1-(4-carbamoylbenzyl)-4-dodecanoyl-3,5-dimethyl-1H-pyrrol-2-yl]propanoic acid
28% inhibition at 0.001 mM
Homo sapiens
5.3.99.3
3-[1-(4-chlorobenzyl)-4-dodecanoyl-3,5-dimethyl-1H-pyrrol-2-yl]propanoic acid
78% inhibition at 0.001 mM
Homo sapiens
5.3.99.3
3-[3-(tert-butylsulfanyl)-1-(4-chlorobenzyl)-5-(propan-2-yl)-1H-indol-2-yl]-2,2-dimethylpropanoic acid
75% inhibition at 0.01 mM
Homo sapiens
5.3.99.3
3-[4-(4-butoxybenzoyl)-1,3,5-trimethyl-1H-pyrrol-2-yl]propanoic acid
32% inhibition at 0.001 mM
Homo sapiens
5.3.99.3
3-[4-dodecanoyl-1-(4-hydroxybenzyl)-3,5-dimethyl-1H-pyrrol-2-yl]propanoic acid
53% inhibition at 0.001 mM
Homo sapiens
5.3.99.3
3-[4-dodecanoyl-1-(4-methoxybenzyl)-3,5-dimethyl-1H-pyrrol-2-yl]propanoic acid
72% inhibition at 0.001 mM
Homo sapiens
5.3.99.3
3-[4-dodecanoyl-3,5-dimethyl-1-(4-methylbenzyl)-1H-pyrrol-2-yl]propanoic acid
52% inhibition at 0.001 mM
Homo sapiens
5.3.99.3
4-(4-dodecanoyl-1,3,5-trimethylpyrrol-2-yl)butanoic acid
70% inhibition at 0.001 mM
Homo sapiens
5.3.99.3
4-dodecanoyl-1,3,5-trimethyl-1H-pyrrole-2-carboxylic acid
37% inhibition at 0.001 mM; 59% inhibition at 0.001 mM
Homo sapiens
5.3.99.3
4-dodecanoyl-3,5-dimethyl-1-phenylpyrrole-2-carboxylic acid
99% inhibition at 0.001 mM
Homo sapiens
5.3.99.3
4-dodecanoyl-3,5-dimethyl-1H-pyrrole-2-carboxylic acid
62% inhibition at 0.001 mM
Homo sapiens
5.3.99.3
4-[[2-(2-carboxyethyl)-4-dodecanoyl-3,5-dimethyl-1H-pyrrol-1-yl]methyl]benzoic acid
27% inhibition at 0.001 mM
Homo sapiens
5.3.99.3
additional information
pyrrole alkanoic acid derivatives as nuisance inhibitors of microsomal prostaglandin E2 synthase-1, overview. No inhibition at 0.001 mM by 3-(4-butanoyl-1,3,5-trimethyl-1H-pyrrol-2-yl)propanoic acid, 3-(4-heptanoyl-1,3,5-trimethyl-1H-pyrrol-2-yl)propanoic acid, 3-(1,3,5-trimethyl-4-octanoyl-1H-pyrrol-2-yl)propanoic acid, 3-(4-decanoyl-1,3,5-trimethyl-1H-pyrrol-2-yl)propanoic acid, 3-[1,3,5-trimethyl-4-[2-(octyloxy)benzoyl]-1H-pyrrol-2-yl]propanoic acid, 3-[4-(3-heptyloxybenzoyl)-1,3,5-trimethylpyrrol-2-yl]propionic acid, 3-(4-benzoyl-1,3,5-trimethyl-1H-pyrrol-2-yl)propanoic acid, 3-[1,3,5-trimethyl-4-(naphthalen-1-ylcarbonyl)-1H-pyrrol-2-yl]propanoic acid, 3-[1,3,5-trimethyl-4-(naphthalen-2-ylcarbonyl)-1H-pyrrol-2-yl]propanoic acid, 3-[4-(2-ethylbenzoyl)-1,3,5-trimethyl-1H-pyrrol-2-yl]propanoic acid, 3-[4-(4-ethylbenzoyl)-1,3,5-trimethyl-1H-pyrrol-2-yl]propanoic acid, 3-[4-(4-benzylbenzoyl)-1,3,5-trimethyl-1H-pyrrol-2-yl]propanoic acid, 4-dodecanoyl-1-methyl-1H-pyrrole-2-carboxylic acid, (4-dodecanoyl-1-methyl-1H-pyrrol-2-yl)acetic acid, and 3-(4-dodecanoyl-1-methyl-1H-pyrrol-2-yl)propanoic acid
Homo sapiens
Localization
EC Number
Localization
Commentary
Organism
GeneOntology No.
Textmining
5.3.99.3
microsome
isozyme mPGES-1
Homo sapiens
-
-
Organism
EC Number
Organism
Primary Accession No. (UniProt)
Commentary
Textmining
5.3.99.3
Homo sapiens
-
microsomal isozyme mPGES-1
-
Substrates and Products (Substrate)
EC Number
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
5.3.99.3
(5Z,13E,15S)-9alpha,11alpha-epidioxy-15-hydroxyprosta-5,13-dienoate
-
727418
Homo sapiens
(5Z,13E,15S)-11alpha,15-dihydroxy-9-oxoprosta-5,13-dienoate
-
-
-
?
Temperature Optimum [°C]
EC Number
Temperature Optimum [°C]
Temperature Optimum Maximum [°C]
Commentary
Organism
5.3.99.3
22
-
assay at room temperature
Homo sapiens
pH Optimum
EC Number
pH Optimum Minimum
pH Optimum Maximum
Commentary
Organism
5.3.99.3
7.2
-
assay at
Homo sapiens
Inhibitors (protein specific)
EC Number
Inhibitors
Commentary
Organism
Structure
5.3.99.3
(1-benzyl-4-dodecanoyl-3,5-dimethyl-1H-pyrrol-2-yl)acetic acid
35% inhibition at 0.001 mM
Homo sapiens
5.3.99.3
(4-dodecanoyl-1,3,5-trimethyl-1H-pyrrol-2-yl)acetic acid
22% inhibition at 0.001 mM
Homo sapiens
5.3.99.3
(4-dodecanoyl-3,5-dimethyl-1H-pyrrol-2-yl)acetic acid
17% inhibition at 0.001 mM
Homo sapiens
5.3.99.3
1-benzyl-4-dodecanoyl-3,5-dimethyl-1H-pyrrole-2-carboxylic acid
65% inhibition at 0.001 mM
Homo sapiens
5.3.99.3
2-(4-dodecanoyl-3,5-dimethyl-1-phenylpyrrol-2-yl)acetic acid
23% inhibition at 0.001 mM
Homo sapiens
5.3.99.3
3-(1,3,5-trimethyl-4-octadecanoyl-1H-pyrrol-2-yl)propanoic acid
97% inhibition at 0.001 mM
Homo sapiens
5.3.99.3
3-(1,3,5-trimethyl-4-tetradecanoyl-1H-pyrrol-2-yl)propanoic acid
91% inhibition at 0.001 mM
Homo sapiens
5.3.99.3
3-(1-benzyl-4-dodecanoyl-3,5-dimethyl-1H-pyrrol-2-yl)propanoic acid
62% inhibition at 0.001 mM
Homo sapiens
5.3.99.3
3-(1-benzyl-4-dodecanoyl-5-methyl-3-phenylpyrrol-2-yl)propionic acid
64% inhibition at 0.001 mM
Homo sapiens
5.3.99.3
3-(4-dodecanoyl-1,3,5-trimethyl-1H-pyrrol-2-yl)propanoic acid
54% inhibition at 0.001 mM
Homo sapiens
5.3.99.3
3-(4-dodecanoyl-1,3,5-trimethylpyrrol-2-yl)-N-(benzenesulfonyl)propanamide
77% inhibition at 0.001 mM
Homo sapiens
5.3.99.3
3-(4-dodecanoyl-1,3,5-trimethylpyrrol-2-yl)-N-(methanesulfonyl)propanamide
52% inhibition at 0.001 mM
Homo sapiens
5.3.99.3
3-(4-dodecanoyl-1,3,5-trimethylpyrrol-2-yl)propanamide
39% inhibition at 0.001 mM
Homo sapiens
5.3.99.3
3-(4-dodecanoyl-1,3,5-trimethylpyrrol-2-yl)propanehydrazide
35% inhibition at 0.001 mM
Homo sapiens
5.3.99.3
3-(4-dodecanoyl-1,3,5-trimethylpyrrol-2-yl)propanenitrile
22% inhibition at 0.001 mM
Homo sapiens
5.3.99.3
3-(4-dodecanoyl-1,5-dimethyl-3-phenyl-1H-pyrrol-2-yl)propanoic acid
90% inhibition at 0.001 mM
Homo sapiens
5.3.99.3
3-(4-dodecanoyl-3,5-dimethyl-1-phenylpyrrol-2-yl)propionic acid
65% inhibition at 0.001 mM
Homo sapiens
5.3.99.3
3-(4-dodecanoyl-3,5-dimethyl-1H-pyrrol-2-yl)propanoic acid
38% inhibition at 0.001 mM
Homo sapiens
5.3.99.3
3-(4-hexadecanoyl-1,3,5-trimethyl-1H-pyrrol-2-yl)propanoic acid
97% inhibition at 0.001 mM
Homo sapiens
5.3.99.3
3-[1-(4-carbamoylbenzyl)-4-dodecanoyl-3,5-dimethyl-1H-pyrrol-2-yl]propanoic acid
28% inhibition at 0.001 mM
Homo sapiens
5.3.99.3
3-[1-(4-chlorobenzyl)-4-dodecanoyl-3,5-dimethyl-1H-pyrrol-2-yl]propanoic acid
78% inhibition at 0.001 mM
Homo sapiens
5.3.99.3
3-[3-(tert-butylsulfanyl)-1-(4-chlorobenzyl)-5-(propan-2-yl)-1H-indol-2-yl]-2,2-dimethylpropanoic acid
75% inhibition at 0.01 mM
Homo sapiens
5.3.99.3
3-[4-(4-butoxybenzoyl)-1,3,5-trimethyl-1H-pyrrol-2-yl]propanoic acid
32% inhibition at 0.001 mM
Homo sapiens
5.3.99.3
3-[4-dodecanoyl-1-(4-hydroxybenzyl)-3,5-dimethyl-1H-pyrrol-2-yl]propanoic acid
53% inhibition at 0.001 mM
Homo sapiens
5.3.99.3
3-[4-dodecanoyl-1-(4-methoxybenzyl)-3,5-dimethyl-1H-pyrrol-2-yl]propanoic acid
72% inhibition at 0.001 mM
Homo sapiens
5.3.99.3
3-[4-dodecanoyl-3,5-dimethyl-1-(4-methylbenzyl)-1H-pyrrol-2-yl]propanoic acid
52% inhibition at 0.001 mM
Homo sapiens
5.3.99.3
4-(4-dodecanoyl-1,3,5-trimethylpyrrol-2-yl)butanoic acid
70% inhibition at 0.001 mM
Homo sapiens
5.3.99.3
4-dodecanoyl-1,3,5-trimethyl-1H-pyrrole-2-carboxylic acid
37% inhibition at 0.001 mM; 59% inhibition at 0.001 mM
Homo sapiens
5.3.99.3
4-dodecanoyl-3,5-dimethyl-1-phenylpyrrole-2-carboxylic acid
99% inhibition at 0.001 mM
Homo sapiens
5.3.99.3
4-dodecanoyl-3,5-dimethyl-1H-pyrrole-2-carboxylic acid
62% inhibition at 0.001 mM
Homo sapiens
5.3.99.3
4-[[2-(2-carboxyethyl)-4-dodecanoyl-3,5-dimethyl-1H-pyrrol-1-yl]methyl]benzoic acid
27% inhibition at 0.001 mM
Homo sapiens
5.3.99.3
additional information
pyrrole alkanoic acid derivatives as nuisance inhibitors of microsomal prostaglandin E2 synthase-1, overview. No inhibition at 0.001 mM by 3-(4-butanoyl-1,3,5-trimethyl-1H-pyrrol-2-yl)propanoic acid, 3-(4-heptanoyl-1,3,5-trimethyl-1H-pyrrol-2-yl)propanoic acid, 3-(1,3,5-trimethyl-4-octanoyl-1H-pyrrol-2-yl)propanoic acid, 3-(4-decanoyl-1,3,5-trimethyl-1H-pyrrol-2-yl)propanoic acid, 3-[1,3,5-trimethyl-4-[2-(octyloxy)benzoyl]-1H-pyrrol-2-yl]propanoic acid, 3-[4-(3-heptyloxybenzoyl)-1,3,5-trimethylpyrrol-2-yl]propionic acid, 3-(4-benzoyl-1,3,5-trimethyl-1H-pyrrol-2-yl)propanoic acid, 3-[1,3,5-trimethyl-4-(naphthalen-1-ylcarbonyl)-1H-pyrrol-2-yl]propanoic acid, 3-[1,3,5-trimethyl-4-(naphthalen-2-ylcarbonyl)-1H-pyrrol-2-yl]propanoic acid, 3-[4-(2-ethylbenzoyl)-1,3,5-trimethyl-1H-pyrrol-2-yl]propanoic acid, 3-[4-(4-ethylbenzoyl)-1,3,5-trimethyl-1H-pyrrol-2-yl]propanoic acid, 3-[4-(4-benzylbenzoyl)-1,3,5-trimethyl-1H-pyrrol-2-yl]propanoic acid, 4-dodecanoyl-1-methyl-1H-pyrrole-2-carboxylic acid, (4-dodecanoyl-1-methyl-1H-pyrrol-2-yl)acetic acid, and 3-(4-dodecanoyl-1-methyl-1H-pyrrol-2-yl)propanoic acid
Homo sapiens
Localization (protein specific)
EC Number
Localization
Commentary
Organism
GeneOntology No.
Textmining
5.3.99.3
microsome
isozyme mPGES-1
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
(5Z,13E,15S)-9alpha,11alpha-epidioxy-15-hydroxyprosta-5,13-dienoate
-
727418
Homo sapiens
(5Z,13E,15S)-11alpha,15-dihydroxy-9-oxoprosta-5,13-dienoate
-
-
-
?
Temperature Optimum [°C] (protein specific)
EC Number
Temperature Optimum [°C]
Temperature Optimum Maximum [°C]
Commentary
Organism
5.3.99.3
22
-
assay at room temperature
Homo sapiens
pH Optimum (protein specific)
EC Number
pH Optimum Minimum
pH Optimum Maximum
Commentary
Organism
5.3.99.3
7.2
-
assay at
Homo sapiens