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Literature summary for 1.1.1.62 extracted from

  • Gargano, E.M.; Allegretta, G.; Perspicace, E.; Carotti, A.; Van Koppen, C.; Frotscher, M.; Marchais-Oberwinkler, S.; Hartmann, R.W.
    17beta-Hydroxysteroid dehydrogenase type 2 inhibition: discovery of selective and metabolically stable compounds inhibiting both the human enzyme and its murine ortholog (2015), PLoS ONE, 10, e0134754.
    View publication on PubMedView publication on EuropePMC

Application

Application Comment Organism
medicine enzyme inhibition can lead to desired increase of estradiol and testosterone levels in the bone tissue and may be used for the treatment of osteoporosis Homo sapiens

Inhibitors

Inhibitors Comment Organism Structure
3'-hydroxy-N-(3-hydroxybenzyl)-N-methylbiphenyl-3-carboxamide
-
Homo sapiens
3'-hydroxy-N-(3-hydroxyphenyl)-N-methylbiphenyl-3-carboxamide 35% inhibition Homo sapiens
3'-methoxy-N-(3-methoxybenzyl)-N-methylbiphenyl-3-carboxamide 11% inhibition Homo sapiens
3'-methoxy-N-(3-methoxyphenyl)-N-methylbiphenyl-3-carboxamide
-
Homo sapiens
3'-methoxy-N-(3-methoxyphenyl)-N-methylbiphenyl-3-carboxamide 1 micromol, 25% inhibition Mus musculus
4'-hydroxy-N-(3-hydroxybenzyl)-N-methylbiphenyl-3-carboxamide
-
Homo sapiens
4'-methoxy-N-(3-methoxyphenyl)-N-methylbiphenyl-3-carboxamide
-
Homo sapiens
4'-methoxy-N-(3-methoxyphenyl)-N-methylbiphenyl-3-carboxamide 1 micromol, 11% inhibition Mus musculus
5-(2-fluoro-3-methoxyphenyl)-N-(3-hydroxybenzyl)-N-methylthiophene-2-carboxamide
-
Homo sapiens
5-(2-fluoro-3-methoxyphenyl)-N-(3-hydroxybenzyl)-N-methylthiophene-2-carboxamide 1 micromol, 65% inhibition Mus musculus
5-(2-fluoro-3-methoxyphenyl)-N-(3-methoxyphenyl)-N-methylthiophene-2-carboxamide
-
Homo sapiens
5-(2-fluoro-3-methoxyphenyl)-N-(3-methoxyphenyl)-N-methylthiophene-2-carboxamide 1 micromol, 26% inhibition Mus musculus
5-(2-fluoro-3-methoxyphenyl)-N-methyl-N-(3-methylphenyl)thiophene-2-carboxamide
-
Homo sapiens
5-(2-fluoro-3-methoxyphenyl)-N-methyl-N-(3-methylphenyl)thiophene-2-carboxamide 1 micromol, 45% inhibition Mus musculus
5-(2-hydroxyphenyl)-N-(3-hydroxyphenyl)-N-methylthiophene-2-carboxamide
-
Homo sapiens
5-(2-hydroxyphenyl)-N-(3-hydroxyphenyl)-N-methylthiophene-2-carboxamide 1 micromol, 18% inhibition Mus musculus
5-(2-methoxyphenyl)-N-(3-methoxyphenyl)-N-methylthiophene-2-carboxamide
-
Homo sapiens
5-(2-methoxyphenyl)-N-(3-methoxyphenyl)-N-methylthiophene-2-carboxamide 1 micromol, 19% inhibition Mus musculus
5-(3-fluorophenyl)-N-(3-hydroxybenzyl)-N-methylthiophene-2-carboxamide
-
Homo sapiens
5-(3-fluorophenyl)-N-(3-hydroxybenzyl)-N-methylthiophene-2-carboxamide 1 micromol, 37% inhibition Mus musculus
5-(3-fluorophenyl)-N-(3-methoxyphenyl)-N-methylthiophene-2-carboxamide
-
Homo sapiens
5-(3-fluorophenyl)-N-(3-methoxyphenyl)-N-methylthiophene-2-carboxamide 1 micromol, 40% inhibition Mus musculus
5-(4-cyanophenyl)-N-(3-hydroxybenzyl)-N-methylthiophene-2-carboxamide
-
Homo sapiens
5-(4-cyanophenyl)-N-(3-methoxyphenyl)-N-methylthiophene-2-carboxamide 48% inhibition Homo sapiens
additional information design of inhibitors displaying h17beta-HSD2 inhibitory activity and selectivity toward h17beta-HSD1. No inhibition by 5-(4-cyanophenyl)-N-(3-hydroxybenzyl)-N-methylthiophene-2-carboxamide Homo sapiens
additional information design of inhibitors displaying h17beta-HSD2 inhibitory activity and selectivity toward h17beta-HSD1. No inhibition by N,5-bis(3-hydroxyphenyl)-N-methylthiophene-2-carboxamide, 5-(4-cyanophenyl)-N-(3-methoxyphenyl)-N-methylthiophene-2-carboxamide, 5-(4-cyanophenyl)-N-(3-methoxyphenyl)-N-methylthiophene-2-carboxamide, 5-(4-cyanophenyl)-N-(3-hydroxybenzyl)-N-methylthiophene-2-carboxamide, 3'-hydroxy-N-(3-hydroxyphenyl)-N-methylbiphenyl-3-carboxamide, and 3'-methoxy-N-(3-methoxybenzyl)-N-methylbiphenyl-3-carboxamide Mus musculus
N,4'-dimethyl-N-(3-methylphenyl)biphenyl-4-carboxamide
-
Homo sapiens
N,4'-dimethyl-N-(3-methylphenyl)biphenyl-4-carboxamide 1 micromol, 50% inhibition Mus musculus
N,5-bis(3-hydroxyphenyl)-N-methylthiophene-2-carboxamide 33% inhibition Homo sapiens
N,5-bis(3-methoxyphenyl)-N-methylthiophene-2-carboxamide
-
Homo sapiens
N,5-bis(3-methoxyphenyl)-N-methylthiophene-2-carboxamide 1 micromol, 29% inhibition Mus musculus
N-(3-hydroxybenzyl)-5-(3-hydroxyphenyl)-N-methylthiophene-2-carboxamide
-
Homo sapiens
N-(3-hydroxybenzyl)-5-(3-hydroxyphenyl)-N-methylthiophene-2-carboxamide 1 micromol, 26% inhibition Mus musculus
N-(3-hydroxybenzyl)-5-(4-hydroxyphenyl)-N-methylthiophene-2-carboxamide
-
Homo sapiens
N-(3-hydroxybenzyl)-5-(4-hydroxyphenyl)-N-methylthiophene-2-carboxamide 1 micromol, 35% inhibition Mus musculus
N-(3-hydroxybenzyl)-N-methyl-5-(3-methylphenyl)thiophene-2-carboxamide
-
Homo sapiens
N-(3-hydroxybenzyl)-N-methyl-5-(3-methylphenyl)thiophene-2-carboxamide 1 micromol, 45% inhibition Mus musculus
N-(3-methoxybenzyl)-5-(3-methoxyphenyl)-N-methylthiophene-2-carboxamide
-
Homo sapiens
N-(3-methoxybenzyl)-5-(3-methoxyphenyl)-N-methylthiophene-2-carboxamide 1 micromol, 16% inhibition Mus musculus
N-(3-methoxyphenyl)-N-methyl-5-(3-methylphenyl)thiophene-2-carboxamide
-
Homo sapiens
N-(3-methoxyphenyl)-N-methyl-5-(3-methylphenyl)thiophene-2-carboxamide 1 micromol, 30% inhibition Mus musculus
N-methyl-N,5-bis(3-methylphenyl)thiophene-2-carboxamide
-
Homo sapiens
N-methyl-N,5-bis(3-methylphenyl)thiophene-2-carboxamide 1 micromol, 42% inhibition Mus musculus

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
17beta-estradiol + NAD+ Homo sapiens
-
estrone + NADH + H+
-
?
17beta-estradiol + NAD+ Mus musculus
-
estrone + NADH + H+
-
?
testosterone + NAD+ Homo sapiens
-
androstenedione + NADH + H+
-
?
testosterone + NAD+ Mus musculus
-
androstenedione + NADH + H+
-
?

Organism

Organism UniProt Comment Textmining
Homo sapiens P37059
-
-
Mus musculus P51658
-
-

Source Tissue

Source Tissue Comment Organism Textmining
bone
-
Homo sapiens
-
bone
-
Mus musculus
-
osteoblast
-
Homo sapiens
-
osteoblast
-
Mus musculus
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
17beta-estradiol + NAD+
-
Homo sapiens estrone + NADH + H+
-
?
17beta-estradiol + NAD+
-
Mus musculus estrone + NADH + H+
-
?
testosterone + NAD+
-
Homo sapiens androstenedione + NADH + H+
-
?
testosterone + NAD+
-
Mus musculus androstenedione + NADH + H+
-
?

Synonyms

Synonyms Comment Organism
17beta-HSD2
-
Homo sapiens
17beta-HSD2
-
Mus musculus
17beta-hydroxysteroid dehydrogenase type 2
-
Homo sapiens
17beta-hydroxysteroid dehydrogenase type 2
-
Mus musculus

Temperature Optimum [°C]

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

pH Optimum

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

Cofactor

Cofactor Comment Organism Structure
NAD+
-
Homo sapiens
NAD+
-
Mus musculus

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.000052
-
pH 7.4, 37°C Homo sapiens N-methyl-N,5-bis(3-methylphenyl)thiophene-2-carboxamide
0.000058
-
pH 7.4, 37°C Homo sapiens N-(3-methoxyphenyl)-N-methyl-5-(3-methylphenyl)thiophene-2-carboxamide
0.000061
-
pH 7.4, 37°C Homo sapiens 5-(2-fluoro-3-methoxyphenyl)-N-(3-hydroxybenzyl)-N-methylthiophene-2-carboxamide
0.000062
-
pH 7.4, 37°C Homo sapiens 5-(2-fluoro-3-methoxyphenyl)-N-(3-methoxyphenyl)-N-methylthiophene-2-carboxamide
0.000062
-
pH 7.4, 37°C Homo sapiens 5-(2-fluoro-3-methoxyphenyl)-N-methyl-N-(3-methylphenyl)thiophene-2-carboxamide
0.000068
-
pH 7.4, 37°C Homo sapiens N,5-bis(3-methoxyphenyl)-N-methylthiophene-2-carboxamide
0.00016
-
pH 7.4, 37°C Homo sapiens N-(3-hydroxybenzyl)-N-methyl-5-(3-methylphenyl)thiophene-2-carboxamide
0.00017
-
pH 7.4, 37°C Homo sapiens 5-(3-fluorophenyl)-N-(3-methoxyphenyl)-N-methylthiophene-2-carboxamide
0.00033
-
pH 7.4, 37°C Homo sapiens 5-(3-fluorophenyl)-N-(3-hydroxybenzyl)-N-methylthiophene-2-carboxamide
0.00033
-
pH 7.4, 37°C Homo sapiens N-(3-hydroxybenzyl)-5-(4-hydroxyphenyl)-N-methylthiophene-2-carboxamide
0.00037
-
pH 7.4, 37°C Homo sapiens N-(3-methoxybenzyl)-5-(3-methoxyphenyl)-N-methylthiophene-2-carboxamide
0.00039
-
pH 7.4, 37°C Homo sapiens N-(3-hydroxybenzyl)-5-(3-hydroxyphenyl)-N-methylthiophene-2-carboxamide
0.00041
-
pH 7.4, 37°C Homo sapiens 5-(2-hydroxyphenyl)-N-(3-hydroxyphenyl)-N-methylthiophene-2-carboxamide
0.00048
-
pH 7.4, 37°C Homo sapiens 4'-hydroxy-N-(3-hydroxybenzyl)-N-methylbiphenyl-3-carboxamide
0.00049
-
pH 7.4, 37°C Homo sapiens 5-(2-methoxyphenyl)-N-(3-methoxyphenyl)-N-methylthiophene-2-carboxamide
0.00051
-
pH 7.4, 37°C Homo sapiens 5-(4-cyanophenyl)-N-(3-methoxyphenyl)-N-methylthiophene-2-carboxamide
0.00052
-
pH 7.4, 37°C Homo sapiens 3'-methoxy-N-(3-methoxyphenyl)-N-methylbiphenyl-3-carboxamide
0.00064
-
pH 7.4, 37°C Homo sapiens 3'-hydroxy-N-(3-hydroxybenzyl)-N-methylbiphenyl-3-carboxamide
0.0011
-
pH 7.4, 37°C Homo sapiens N,4'-dimethyl-N-(3-methylphenyl)biphenyl-4-carboxamide
0.0012
-
pH 7.4, 37°C Homo sapiens 4'-methoxy-N-(3-methoxyphenyl)-N-methylbiphenyl-3-carboxamide

General Information

General Information Comment Organism
malfunction enzyme inhibition can lead to desired increase of estradiol and testosterone levels in the bone tissue and may be used for the treatment of osteoporosis Homo sapiens
malfunction enzyme inhibition can lead to desired increase of estradiol and testosterone levels in the bone tissue and may be used for the treatment of osteoporosis Mus musculus
physiological function the drop in 17beta-estradiol (E2) and testosterone levels, occurring with ageing, is the main factor driving the onset and progression of osteoporosis Homo sapiens
physiological function the drop in 17beta-estradiol (E2) and testosterone levels, occurring with ageing, is the main factor driving the onset and progression of osteoporosis Mus musculus