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Literature summary extracted from
- Self-organizing molecular field analysis on pregnane derivatives as human steroidal 5alpha-reductase inhibitors (2010), Steroids, 75, 411-418.
Inhibitors
| EC Number | Inhibitors | Comment | Organism | Structure |
|---|---|---|---|---|
| 1.3.99.5 | (16beta)-16-methyl-3,20-dioxopregna-4,6-dien-17-yl acetate | - |
Homo sapiens |  |
| 1.3.99.5 | (16beta)-16-methyl-3,20-dioxopregna-4,6-dien-17-yl butanoate | - |
Homo sapiens | |
| 1.3.99.5 | (16beta)-16-methyl-3,20-dioxopregna-4,6-dien-17-yl pentanoate | - |
Homo sapiens | |
| 1.3.99.5 | (16beta)-16-methyl-3,20-dioxopregna-4,6-dien-17-yl phenylacetate | - |
Homo sapiens | |
| 1.3.99.5 | (2R,3R,10aR,12aS)-2,10a,12a-trimethyl-1,8-dioxo-3-phenyl-1,2,3,4,4a,4b,8,9,10,10a,10b,11,12,12a-tetradecahydrochrysen-2-yl (2-fluorophenyl)acetate | - |
Homo sapiens | |
| 1.3.99.5 | (2R,3R,10aR,12aS)-2,10a,12a-trimethyl-1,8-dioxo-3-phenyl-1,2,3,4,4a,4b,8,9,10,10a,10b,11,12,12a-tetradecahydrochrysen-2-yl (3-fluorophenyl)acetate | - |
Homo sapiens | |
| 1.3.99.5 | (2R,3R,10aR,12aS)-2,10a,12a-trimethyl-1,8-dioxo-3-phenyl-1,2,3,4,4a,4b,8,9,10,10a,10b,11,12,12a-tetradecahydrochrysen-2-yl phenylacetate | - |
Homo sapiens | |
| 1.3.99.5 | (4alpha,5alpha)-3,20-dioxo-4,5-epoxypregnan-17-yl 4-bromobenzoate | - |
Homo sapiens | |
| 1.3.99.5 | (4alpha,5alpha)-3,20-dioxo-4,5-epoxypregnan-17-yl benzoate | - |
Homo sapiens | |
| 1.3.99.5 | (5alpha,6alpha)-20-oxo-5,6-epoxypregn-16-en-3-yl acetate | - |
Homo sapiens | |
| 1.3.99.5 | 17-hydroxypregna-4,6-diene-3,20-dione | - |
Homo sapiens | |
| 1.3.99.5 | 3,20-dioxopregna-4,6-dien-17-yl (4-bromophenyl)carbamate | - |
Homo sapiens | |
| 1.3.99.5 | 3,20-dioxopregna-4,6-dien-17-yl 4-bromobenzoate | - |
Homo sapiens | |
| 1.3.99.5 | 3,20-dioxopregna-4,6-dien-17-yl 4-chlorobenzoate | - |
Homo sapiens | |
| 1.3.99.5 | 3,20-dioxopregna-4,6-dien-17-yl 4-fluorobenzoate | - |
Homo sapiens | |
| 1.3.99.5 | 3,20-dioxopregna-4,6-dien-17-yl benzoate | - |
Homo sapiens | |
| 1.3.99.5 | 3,20-dioxopregna-4,6-dien-17-yl phenylcarbamate | - |
Homo sapiens | |
| 1.3.99.5 | 6,20-dioxopregna-4,16-dien-3-yl 3-bromopropanoate | - |
Homo sapiens | |
| 1.3.99.5 | 6,20-dioxopregna-4,16-dien-3-yl 3-chloropropanoate | - |
Homo sapiens | |
| 1.3.99.5 | 6,20-dioxopregna-4,16-dien-3-yl 3-iodopropanoate | - |
Homo sapiens | |
| 1.3.99.5 | 6,20-dioxopregna-4,16-dien-3-yl acetate | - |
Homo sapiens | |
| 1.3.99.5 | 6,20-dioxopregna-4,16-dien-3-yl benzoate | - |
Homo sapiens | |
| 1.3.99.5 | 6-bromo-3,20-dioxopregna-4,6-dien-17-yl acetate | - |
Homo sapiens | |
| 1.3.99.5 | 6-chloro-3,20-dioxopregna-4,6-dien-17-yl 4-bromobenzoate | - |
Homo sapiens | |
| 1.3.99.5 | 6-chloro-3,20-dioxopregna-4,6-dien-17-yl 4-chlorobenzoate | - |
Homo sapiens | |
| 1.3.99.5 | 6-chloro-3,20-dioxopregna-4,6-dien-17-yl 4-fluorobenzoate | - |
Homo sapiens | |
| 1.3.99.5 | 6-chloro-3,20-dioxopregna-4,6-dien-17-yl benzoate | - |
Homo sapiens | |
| 1.3.99.5 | finasteride | i.e. 17beta-(N-tert-butylcarbamoyl)-4-aza-5alpha-androst-1-en-3-one or MK-906. A competitive inhibitor of 5alpha-reductase type II with 10fold higher affinity than type I due to formation of stable complex with enzyme | Homo sapiens | |
| 1.3.99.5 | additional information | design and optimization of steroidal structure as 5alpha-reductase inhibitors, rationalizing the molecular properties and 5alpha-reductase inhibitory activities, three-dimensional quantitative structure-activity relationship, 3D-QSAR, study and modeling, overview | Homo sapiens | |
| 1.3.99.5 | pregna-4,16-diene-3,6,20-trione | - |
Homo sapiens | |
| 1.3.99.5 | progesterone | inhibits the synthesis of 5alpha-dihydrotestosterone by competing with 4-en-3-one function of the testosterone for the 5alpha-reductase enzyme | Homo sapiens | |
KM Value [mM]
| EC Number | KM Value [mM] | KM Value Maximum [mM] | Substrate | Comment | Organism | Structure |
|---|---|---|---|---|---|---|
| 1.3.99.5 | 0.0004 | - |
testosterone | type II isozyme, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | |
| 1.3.99.5 | 0.01 | - |
testosterone | type I isozyme, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | |
Localization
| EC Number | Localization | Comment | Organism | GeneOntology No. | Textmining |
|---|---|---|---|---|---|
| 1.3.99.5 | membrane | - |
Homo sapiens | 16020 | - |
Natural Substrates/ Products (Substrates)
| EC Number | Natural Substrates | Organism | Comment (Nat. Sub.) | Natural Products | Comment (Nat. Pro.) | Rev. | Reac. |
|---|---|---|---|---|---|---|---|
| 1.3.99.5 | 5alpha-dihydrotestosterone + NADP+ | Homo sapiens | the enzyme performs conversion of testosterone to 5alpha-dihydrotestosterone | testosterone + NADPH + H+ | - |
r | |
Organism
| EC Number | Organism | UniProt | Comment | Textmining |
|---|---|---|---|---|
| 1.3.99.5 | Homo sapiens | - |
- |
- |
Substrates and Products (Substrate)
| EC Number | Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
|---|---|---|---|---|---|---|---|
| 1.3.99.5 | 5alpha-dihydrotestosterone + NADP+ | - |
Homo sapiens | testosterone + NADPH + H+ | - |
r | |
| 1.3.99.5 | 5alpha-dihydrotestosterone + NADP+ | the enzyme performs conversion of testosterone to 5alpha-dihydrotestosterone | Homo sapiens | testosterone + NADPH + H+ | - |
r | |
Synonyms
| EC Number | Synonyms | Comment | Organism |
|---|---|---|---|
| 1.3.99.5 | 5alpha-reductase | - |
Homo sapiens |
| 1.3.99.5 | NADPH-dependent 5alpha-reductase enzyme | - |
Homo sapiens |
pH Optimum
| EC Number | pH Optimum Minimum | pH Optimum Maximum | Comment | Organism |
|---|---|---|---|---|
| 1.3.99.5 | 5.5 | - |
type II isozyme | Homo sapiens |
| 1.3.99.5 | 6.5 | 9 | type I isozyme | Homo sapiens |
Cofactor
| EC Number | Cofactor | Comment | Organism | Structure |
|---|---|---|---|---|
| 1.3.99.5 | NADP+ | - |
Homo sapiens | |
| 1.3.99.5 | NADPH | - |
Homo sapiens | |
IC50 Value
| EC Number | IC50 Value | IC50 Value Maximum | Comment | Organism | Inhibitor | Structure |
|---|---|---|---|---|---|---|
| 1.3.99.5 | 0.000000063 | - |
pH not specified in the publication, temperature not specified in the publication | Homo sapiens | (5alpha,6alpha)-20-oxo-5,6-epoxypregn-16-en-3-yl acetate | |
| 1.3.99.5 | 0.000000063 | - |
pH not specified in the publication, temperature not specified in the publication | Homo sapiens | (16beta)-16-methyl-3,20-dioxopregna-4,6-dien-17-yl acetate | |
| 1.3.99.5 | 0.000000065 | - |
pH not specified in the publication, temperature not specified in the publication | Homo sapiens | 6,20-dioxopregna-4,16-dien-3-yl acetate | |
| 1.3.99.5 | 0.00000007 | - |
pH not specified in the publication, temperature not specified in the publication | Homo sapiens | 6,20-dioxopregna-4,16-dien-3-yl benzoate | |
| 1.3.99.5 | 0.000000079 | - |
pH not specified in the publication, temperature not specified in the publication | Homo sapiens | (16beta)-16-methyl-3,20-dioxopregna-4,6-dien-17-yl butanoate | |
| 1.3.99.5 | 0.0000005 | - |
pH not specified in the publication, temperature not specified in the publication | Homo sapiens | (2R,3R,10aR,12aS)-2,10a,12a-trimethyl-1,8-dioxo-3-phenyl-1,2,3,4,4a,4b,8,9,10,10a,10b,11,12,12a-tetradecahydrochrysen-2-yl (2-fluorophenyl)acetate | |
| 1.3.99.5 | 0.0000007 | - |
pH not specified in the publication, temperature not specified in the publication | Homo sapiens | (2R,3R,10aR,12aS)-2,10a,12a-trimethyl-1,8-dioxo-3-phenyl-1,2,3,4,4a,4b,8,9,10,10a,10b,11,12,12a-tetradecahydrochrysen-2-yl (3-fluorophenyl)acetate | |
| 1.3.99.5 | 0.00000085 | - |
pH not specified in the publication, temperature not specified in the publication | Homo sapiens | pregna-4,16-diene-3,6,20-trione | |
| 1.3.99.5 | 0.0000012 | - |
pH not specified in the publication, temperature not specified in the publication | Homo sapiens | (16beta)-16-methyl-3,20-dioxopregna-4,6-dien-17-yl phenylacetate | |
| 1.3.99.5 | 0.0000049 | - |
pH not specified in the publication, temperature not specified in the publication | Homo sapiens | (4alpha,5alpha)-3,20-dioxo-4,5-epoxypregnan-17-yl 4-bromobenzoate | |
| 1.3.99.5 | 0.00001 | - |
pH not specified in the publication, temperature not specified in the publication | Homo sapiens | 3,20-dioxopregna-4,6-dien-17-yl phenylcarbamate | |
| 1.3.99.5 | 0.00001 | - |
pH not specified in the publication, temperature not specified in the publication | Homo sapiens | 6,20-dioxopregna-4,16-dien-3-yl 3-iodopropanoate | |
| 1.3.99.5 | 0.000013 | - |
pH not specified in the publication, temperature not specified in the publication | Homo sapiens | (4alpha,5alpha)-3,20-dioxo-4,5-epoxypregnan-17-yl benzoate | |
| 1.3.99.5 | 0.000014 | - |
pH not specified in the publication, temperature not specified in the publication | Homo sapiens | 6,20-dioxopregna-4,16-dien-3-yl 3-chloropropanoate | |
| 1.3.99.5 | 0.000018 | - |
pH not specified in the publication, temperature not specified in the publication | Homo sapiens | 6,20-dioxopregna-4,16-dien-3-yl 3-bromopropanoate | |
| 1.3.99.5 | 0.000026 | - |
pH not specified in the publication, temperature not specified in the publication | Homo sapiens | 3,20-dioxopregna-4,6-dien-17-yl 4-fluorobenzoate | |
| 1.3.99.5 | 0.000031 | - |
pH not specified in the publication, temperature not specified in the publication | Homo sapiens | 3,20-dioxopregna-4,6-dien-17-yl 4-bromobenzoate | |
| 1.3.99.5 | 0.000032 | - |
pH not specified in the publication, temperature not specified in the publication | Homo sapiens | (16beta)-16-methyl-3,20-dioxopregna-4,6-dien-17-yl pentanoate | |
| 1.3.99.5 | 0.000033 | - |
pH not specified in the publication, temperature not specified in the publication | Homo sapiens | 6-bromo-3,20-dioxopregna-4,6-dien-17-yl acetate | |
| 1.3.99.5 | 0.00005 | - |
pH not specified in the publication, temperature not specified in the publication | Homo sapiens | 3,20-dioxopregna-4,6-dien-17-yl (4-bromophenyl)carbamate | |
| 1.3.99.5 | 0.000063 | - |
pH not specified in the publication, temperature not specified in the publication | Homo sapiens | 3,20-dioxopregna-4,6-dien-17-yl benzoate | |
| 1.3.99.5 | 0.00009 | - |
pH not specified in the publication, temperature not specified in the publication | Homo sapiens | 3,20-dioxopregna-4,6-dien-17-yl 4-chlorobenzoate | |
| 1.3.99.5 | 0.00011 | - |
pH not specified in the publication, temperature not specified in the publication | Homo sapiens | 17-hydroxypregna-4,6-diene-3,20-dione | |
| 1.3.99.5 | 0.00031 | - |
pH not specified in the publication, temperature not specified in the publication | Homo sapiens | (2R,3R,10aR,12aS)-2,10a,12a-trimethyl-1,8-dioxo-3-phenyl-1,2,3,4,4a,4b,8,9,10,10a,10b,11,12,12a-tetradecahydrochrysen-2-yl phenylacetate | |
| 1.3.99.5 | 0.00036 | - |
pH not specified in the publication, temperature not specified in the publication | Homo sapiens | 3,20-dioxopregna-4,6-dien-17-yl benzoate | |
| 1.3.99.5 | 0.00037 | - |
pH not specified in the publication, temperature not specified in the publication | Homo sapiens | 3,20-dioxopregna-4,6-dien-17-yl 4-bromobenzoate | |
| 1.3.99.5 | 0.00092 | - |
pH not specified in the publication, temperature not specified in the publication | Homo sapiens | 6-chloro-3,20-dioxopregna-4,6-dien-17-yl benzoate | |
| 1.3.99.5 | 0.00093 | - |
pH not specified in the publication, temperature not specified in the publication | Homo sapiens | 6-chloro-3,20-dioxopregna-4,6-dien-17-yl 4-fluorobenzoate | |
| 1.3.99.5 | 0.00097 | - |
pH not specified in the publication, temperature not specified in the publication | Homo sapiens | 6-chloro-3,20-dioxopregna-4,6-dien-17-yl 4-bromobenzoate | |
| 1.3.99.5 | 0.00099 | - |
pH not specified in the publication, temperature not specified in the publication | Homo sapiens | 6-chloro-3,20-dioxopregna-4,6-dien-17-yl 4-chlorobenzoate | |
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