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16alpha-hydroxytestosterone + 3 O2 + 3 reduced flavoprotein
(16alpha,17beta)-estra-1(10),2,4-triene-3,16,17-triol + formate + 4 H2O + 3 oxidized flavoprotein
-
overall reaction
-
-
?
19-hydroxyandrost-4-ene-3,17-dione + O2 + a reduced flavoprotein
19-oxo-androst-4-ene-3,17-dione + 2 H2O + an oxidized flavoprotein
19-oxoandrost-4-ene-3,17-dione + O2 + a reduced flavoprotein
estrone + formate + H2O + an oxidized flavoprotein
-
-
-
-
?
7-methoxy-4-trifluoromethyl coumarin + H2O + oxidized flavoprotein
? + O2 + reduced flavoprotein
-
-
-
-
?
androst-4-ene-3,17-dione + 3 O2 + 3 reduced flavoproteins
estrone + formate + 4 H2O + 3 oxidized flavoproteins
androst-4-ene-3,17-dione + O2 + a reduced flavoprotein
19-hydroxyandrost-4-ene-3,17-dione + H2O + an oxidized flavoprotein
-
-
-
-
?
testosterone + 3 O2 + 3 reduced flavoproteins
17beta-estradiol + formate + 4 H2O + 3 oxidized flavoproteins
additional information
?
-
19-hydroxyandrost-4-ene-3,17-dione + O2 + a reduced flavoprotein
19-oxo-androst-4-ene-3,17-dione + 2 H2O + an oxidized flavoprotein
-
-
-
?
19-hydroxyandrost-4-ene-3,17-dione + O2 + a reduced flavoprotein
19-oxo-androst-4-ene-3,17-dione + 2 H2O + an oxidized flavoprotein
-
-
-
-
?
androst-4-ene-3,17-dione + 3 O2 + 3 reduced flavoproteins
estrone + formate + 4 H2O + 3 oxidized flavoproteins
-
-
-
?
androst-4-ene-3,17-dione + 3 O2 + 3 reduced flavoproteins
estrone + formate + 4 H2O + 3 oxidized flavoproteins
-
-
-
-
?
androst-4-ene-3,17-dione + 3 O2 + 3 reduced flavoproteins
estrone + formate + 4 H2O + 3 oxidized flavoproteins
-
-
-
?
androst-4-ene-3,17-dione + 3 O2 + 3 reduced flavoproteins
estrone + formate + 4 H2O + 3 oxidized flavoproteins
-
-
-
-
?
androst-4-ene-3,17-dione + 3 O2 + 3 reduced flavoproteins
estrone + formate + 4 H2O + 3 oxidized flavoproteins
-
-
-
?
androst-4-ene-3,17-dione + 3 O2 + 3 reduced flavoproteins
estrone + formate + 4 H2O + 3 oxidized flavoproteins
-
-
-
-
?
androst-4-ene-3,17-dione + 3 O2 + 3 reduced flavoproteins
estrone + formate + 4 H2O + 3 oxidized flavoproteins
-
-
overall reaction
-
?
androst-4-ene-3,17-dione + 3 O2 + 3 reduced flavoproteins
estrone + formate + 4 H2O + 3 oxidized flavoproteins
-
overall reaction
-
-
?
androst-4-ene-3,17-dione + 3 O2 + 3 reduced flavoproteins
estrone + formate + 4 H2O + 3 oxidized flavoproteins
-
-
-
?
testosterone + 3 O2 + 3 reduced flavoproteins
17beta-estradiol + formate + 4 H2O + 3 oxidized flavoproteins
-
-
-
?
testosterone + 3 O2 + 3 reduced flavoproteins
17beta-estradiol + formate + 4 H2O + 3 oxidized flavoproteins
-
-
-
-
?
testosterone + 3 O2 + 3 reduced flavoproteins
17beta-estradiol + formate + 4 H2O + 3 oxidized flavoproteins
-
overall reaction
-
-
?
additional information
?
-
androstenedione is the preferred substrate, the affinity of the intermediates progressively decrease with increased oxidation
-
-
-
additional information
?
-
-
androstenedione is the preferred substrate, the affinity of the intermediates progressively decrease with increased oxidation
-
-
-
additional information
?
-
-
19-oxygenated androgen intermediates are biosynthesized sequentially in a step-wise fashion as the cytochrome P450 and NADPH-cytochrome P450 reductase form transient complexes, and the amount of isolatable 19-oxygenated androgen is proportional to the amount of excess cytochrome P450 component
-
-
?
additional information
?
-
-
the aromatization of androstenedione probably involves two successive hydroxylations at the C-19 methyl group, mediated by a common catalytic site with the third and rate-determining 2beta-hydroxylation taking place at a different enzyme site
-
-
?
additional information
?
-
-
the rate of entry of the first electron into the oxidized P450 substrate complex may be rate limiting in the aromatization of C19 but not C18 steroids
-
-
?
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(E)-2,4-dimethoxy-N-(4-(phenyldiazenyl)phenyl)benzenesulfonamide
not effective on HFF-1 cells
-
(E)-4-cyano-N-(4-(phenyldiazenyl)phenyl)benzenesulfonamide
not effective on HFF-1 cells
-
(E)-N-((1H-benzo[d]imidazole-2-yl)methyl)-2,4-dimethoxy-N-(4-(phenyldiazenyl)phenyl)benzenesulfonamide
treatment induces a dose-dependent increase of the percentage of cells found in the apoptotic stage, compound shows an anti-proliferative effect on MCF-7 cells, being blocked in the G1/S phase checkpoint. Compound is not effective on HFF-1 cells
-
1,4,6-androstatriene-3,17-dione
-
treatment with the aromatase inhibitor ATD results in significantly decreased aromatase activity in male and female brain,but has no significant impact on ovarian aromatase activity
1-(3-bromo-4-methoxybenzene-1-sulfonyl)-3-[(1H-imidazol-1-yl)methyl]piperidine
-
-
1-[3-(2-chloro-6-nitrophenyl)benzene-1-sulfonyl]-3-[(1H-imidazol-1-yl)methyl]piperidine
-
-
17beta,11alpha-dihydroxy-17alpha-methylandrosta-2-oxa-4-ene-3-one
-
-
19-hydroxyandrost-4-ene-3,17-dione
19-nortestosterone
-
competitive inhibitor of both aromatization and cytochrome P450 binding of androst-4-ene-3,17-dione
19-oxoandrost-4-ene-3,17-dione
2-(pyridin-3-yl)-1H-indole
-
2-phenyl-1H-indole-3-carbonitrile
-
3-(4-(1H-benzo[d]imidazol-2-yl)phenyl)-6-(4-cyanophenyl)-7H-[1,2,4]triazole[3,4-b][1,3,4]thiadiazine
-
-
3-(4-(1H-benzo[d]imidazol-2-yl)phenyl)-6-(4-fluorophenyl)-7H-[1,2,4]triazole[3,4-b][1,3,4]thiadiazine
-
-
3-(4-(5-chloro-1H-benzo[d]imidazol-2-yl)phenyl)-6-(4-cyanophenyl)-7H-[1,2,4]triazole [3,4-b][1,3,4]thiadiazine
-
-
3-(4-(5-chloro-1H-benzo[d]imidazol-2-yl)phenyl)-6-(4-fluorophenyl)-7H-[1,2,4]triazole [3,4-b][1,3,4]thiadiazine
-
-
4-[3-[(1H-imidazol-1-yl)methyl]piperidine-1-sulfonyl]-2,1,3-benzothiadiazole
-
-
5-nitro-2-phenyl-1H-indole
compound is inhibitory toward aromatase and induces quinone reductase 1
6alpha-allylandrost-4-ene-3,17-dione
-
-
6alpha-allylandrosta-1,4-diene-3,17-dione
competitive, irreversible, at 0.010 mM 99.2% inhibition of activity in MCF-7aro cells
-
6alpha-methylandrost-4-en-17-one
-
-
6alpha-methylandrost-4-ene-3,17-dione
competitive, reversible, at 0.010 mM 98.5% inhibition of activity in MCF-7aro cells
-
7,8-Benzoflavone
-
competitive inhibitor, induces spectral changes in the aromatase cytochrome P450
7alpha-allyl-4-hydroxyandrost-4-ene-3,17-dione
-
-
8-prenylnaringenin
-
flavonoid isolated from hop, inhibits enzyme activity, no effect on enzyme expression
Aminoglutethimide
-
0.005 mM, 54% residual activity
androst-4-ene-3,17-dione
-
competitive inhibitor of both aromatization and cytochrome P450 binding of 19-nortestosterone
chrysin
-
competitive inhibitor, induces spectral changes in the aromatase cytochrome P450
diethylaminoethyl-2,2-diphenylvalerate
-
0.05 mM, 64% residual activity
ganaxolone
steroidal anti-epileptic drug
-
isoxanthohumol
-
flavonoid isolated from hop, inhibits enzyme activity, no effect on enzyme expression
KCN
-
5 mM, 80% residual activity
oxandrolone
steroidal anabolic drug
-
sildenafil
partial and mixed inhibitor with a maximal inhibition of 35%, KD value 0.58 mM. Sildenafil binds to the heme iron via its 6th axial water ligand
SYN 20028567
-
nonsteroidal lead compound for aromatase inhibition
xanthohumol
-
flavonoid isolated from hop, inhibits enzyme activity, no effect on enzyme expression
19-hydroxyandrost-4-ene-3,17-dione
-
competitive with substrates androst-4-ene-3,17-dione and 19-oxoandrost-4-ene-3,17-dione
19-hydroxyandrost-4-ene-3,17-dione
-
competitively inhibits the formation of 19-hydroxyandrost-4-ene-3,17-dione and estrogen
19-oxoandrost-4-ene-3,17-dione
-
competitive with substrates androst-4-ene-3,17-dione and 19-hydroxyandrost-4-ene-3,17-dione
19-oxoandrost-4-ene-3,17-dione
-
competitively inhibits the formation of 19-oxoandrost-4-ene-3,17-dione and estrogen
anastrozole
two-step binding mechanism, Kd value 0.0002 mM
anastrozole
azole inhibitor, binding is independent of pH
exemestane
steroidal inhibitor, binding is dependent of pH
imazalil
-
inhibition of aromatase activity in Polyodon spathula, Esox lucius, Catostomus commersonii, Oncorhynchus mykiss, and Pimephales promelas. The rank order of potency for these fishes based on IC50 is fadrozole > letrozole > imazalil > prochloraz = propiconazole. On average, fadrozole is 5-, 10-, 250-, and 50fold more potent than letrozole, imazalil, prochloraz, and propiconazole, respectively
imazalil
-
inhibition of aromatase activity in Polyodon spathula, Esox lucius, Catostomus commersonii, Oncorhynchus mykiss, and Pimephales promelas. The rank order of potency for these fishes based on IC50 is fadrozole > letrozole > imazalil > prochloraz = propiconazole. On average, fadrozole is 5-, 10-, 250-, and 50fold more potent than letrozole, imazalil, prochloraz, and propiconazole, respectively
imazalil
-
inhibition of aromatase activity in Polyodon spathula, Esox lucius, Catostomus commersonii, Oncorhynchus mykiss, and Pimephales promelas. The rank order of potency for these fishes based on IC50 is fadrozole > letrozole > imazalil > prochloraz = propiconazole. On average, fadrozole is 5-, 10-, 250-, and 50fold more potent than letrozole, imazalil, prochloraz, and propiconazole, respectively
imazalil
-
inhibition of aromatase activity in Polyodon spathula, Esox lucius, Catostomus commersonii, Oncorhynchus mykiss, and Pimephales promelas. The rank order of potency for these fishes based on IC50 is fadrozole > letrozole > imazalil > prochloraz = propiconazole. On average, fadrozole is 5-, 10-, 250-, and 50fold more potent than letrozole, imazalil, prochloraz, and propiconazole, respectively
imazalil
-
inhibition of aromatase activity in Polyodon spathula, Esox lucius, Catostomus commersonii, Oncorhynchus mykiss, and Pimephales promelas. The rank order of potency for these fishes based on IC50 is fadrozole > letrozole > imazalil > prochloraz = propiconazole. On average, fadrozole is 5-, 10-, 250-, and 50fold more potent than letrozole, imazalil, prochloraz, and propiconazole, respectively
letrozole
-
inhibition of aromatase activity in Polyodon spathula, Esox lucius, Catostomus commersonii, Oncorhynchus mykiss, and Pimephales promelas. The rank order of potency for these fishes based on IC50 is fadrozole > letrozole > imazalil > prochloraz = propiconazole. On average, fadrozole is 5-, 10-, 250-, and 50fold more potent than letrozole, imazalil, prochloraz, and propiconazole, respectively
letrozole
-
inhibition of aromatase activity in Polyodon spathula, Esox lucius, Catostomus commersonii, Oncorhynchus mykiss, and Pimephales promelas. The rank order of potency for these fishes based on IC50 is fadrozole > letrozole > imazalil > prochloraz = propiconazole. On average, fadrozole is 5-, 10-, 250-, and 50fold more potent than letrozole, imazalil, prochloraz, and propiconazole, respectively
letrozole
0.001 mM, complete inhibition of activity in cell lines
letrozole
-
inhibition of aromatase activity in Polyodon spathula, Esox lucius, Catostomus commersonii, Oncorhynchus mykiss, and Pimephales promelas. The rank order of potency for these fishes based on IC50 is fadrozole > letrozole > imazalil > prochloraz = propiconazole. On average, fadrozole is 5-, 10-, 250-, and 50fold more potent than letrozole, imazalil, prochloraz, and propiconazole, respectively
letrozole
-
inhibition of aromatase activity in Polyodon spathula, Esox lucius, Catostomus commersonii, Oncorhynchus mykiss, and Pimephales promelas. The rank order of potency for these fishes based on IC50 is fadrozole > letrozole > imazalil > prochloraz = propiconazole. On average, fadrozole is 5-, 10-, 250-, and 50fold more potent than letrozole, imazalil, prochloraz, and propiconazole, respectively
letrozole
-
inhibition of aromatase activity in Polyodon spathula, Esox lucius, Catostomus commersonii, Oncorhynchus mykiss, and Pimephales promelas. The rank order of potency for these fishes based on IC50 is fadrozole > letrozole > imazalil > prochloraz = propiconazole. On average, fadrozole is 5-, 10-, 250-, and 50fold more potent than letrozole, imazalil, prochloraz, and propiconazole, respectively
Prochloraz
-
inhibition of aromatase activity in Polyodon spathula, Esox lucius, Catostomus commersonii, Oncorhynchus mykiss, and Pimephales promelas. The rank order of potency for these fishes based on IC50 is fadrozole > letrozole > imazalil > prochloraz = propiconazole. On average, fadrozole is 5-, 10-, 250-, and 50fold more potent than letrozole, imazalil, prochloraz, and propiconazole, respectively
Prochloraz
-
inhibition of aromatase activity in Polyodon spathula, Esox lucius, Catostomus commersonii, Oncorhynchus mykiss, and Pimephales promelas. The rank order of potency for these fishes based on IC50 is fadrozole > letrozole > imazalil > prochloraz = propiconazole. On average, fadrozole is 5-, 10-, 250-, and 50fold more potent than letrozole, imazalil, prochloraz, and propiconazole, respectively
Prochloraz
-
inhibition of aromatase activity in Polyodon spathula, Esox lucius, Catostomus commersonii, Oncorhynchus mykiss, and Pimephales promelas. The rank order of potency for these fishes based on IC50 is fadrozole > letrozole > imazalil > prochloraz = propiconazole. On average, fadrozole is 5-, 10-, 250-, and 50fold more potent than letrozole, imazalil, prochloraz, and propiconazole, respectively
Prochloraz
-
inhibition of aromatase activity in Polyodon spathula, Esox lucius, Catostomus commersonii, Oncorhynchus mykiss, and Pimephales promelas. The rank order of potency for these fishes based on IC50 is fadrozole > letrozole > imazalil > prochloraz = propiconazole. On average, fadrozole is 5-, 10-, 250-, and 50fold more potent than letrozole, imazalil, prochloraz, and propiconazole, respectively
Prochloraz
-
inhibition of aromatase activity in Polyodon spathula, Esox lucius, Catostomus commersonii, Oncorhynchus mykiss, and Pimephales promelas. The rank order of potency for these fishes based on IC50 is fadrozole > letrozole > imazalil > prochloraz = propiconazole. On average, fadrozole is 5-, 10-, 250-, and 50fold more potent than letrozole, imazalil, prochloraz, and propiconazole, respectively
Propiconazole
-
inhibition of aromatase activity in Polyodon spathula, Esox lucius, Catostomus commersonii, Oncorhynchus mykiss, and Pimephales promelas. The rank order of potency for these fishes based on IC50 is fadrozole > letrozole > imazalil > prochloraz = propiconazole. On average, fadrozole is 5-, 10-, 250-, and 50fold more potent than letrozole, imazalil, prochloraz, and propiconazole, respectively
Propiconazole
-
inhibition of aromatase activity in Polyodon spathula, Esox lucius, Catostomus commersonii, Oncorhynchus mykiss, and Pimephales promelas. The rank order of potency for these fishes based on IC50 is fadrozole > letrozole > imazalil > prochloraz = propiconazole. On average, fadrozole is 5-, 10-, 250-, and 50fold more potent than letrozole, imazalil, prochloraz, and propiconazole, respectively
Propiconazole
-
inhibition of aromatase activity in Polyodon spathula, Esox lucius, Catostomus commersonii, Oncorhynchus mykiss, and Pimephales promelas. The rank order of potency for these fishes based on IC50 is fadrozole > letrozole > imazalil > prochloraz = propiconazole. On average, fadrozole is 5-, 10-, 250-, and 50fold more potent than letrozole, imazalil, prochloraz, and propiconazole, respectively
Propiconazole
-
inhibition of aromatase activity in Polyodon spathula, Esox lucius, Catostomus commersonii, Oncorhynchus mykiss, and Pimephales promelas. The rank order of potency for these fishes based on IC50 is fadrozole > letrozole > imazalil > prochloraz = propiconazole. On average, fadrozole is 5-, 10-, 250-, and 50fold more potent than letrozole, imazalil, prochloraz, and propiconazole, respectively
Propiconazole
-
inhibition of aromatase activity in Polyodon spathula, Esox lucius, Catostomus commersonii, Oncorhynchus mykiss, and Pimephales promelas. The rank order of potency for these fishes based on IC50 is fadrozole > letrozole > imazalil > prochloraz = propiconazole. On average, fadrozole is 5-, 10-, 250-, and 50fold more potent than letrozole, imazalil, prochloraz, and propiconazole, respectively
additional information
-
treatment with alkaline phosphatase results in loss of activity, as well as incubation in phosphate-free buffer
-
additional information
-
not inhibitory: 5,6-benzoflavone
-
additional information
-
lager beer, alcohol-free beer, stout beer, and xanthohumol-rich stout beer significantly decrease aromatase activity
-
additional information
for modification of androstane inhibotrs, position C-6alpha is better to functionalize than C-7alpha, except when there is a C-4 substituent simultaneously
-
additional information
analysis of triazoles, diazoles, and thiazoles for their reversible inhibition and agonist activity. The chemical nature and position of substituents (chemical groups) on diazoles and triazole ring have different contributions to inhibition, while functional groups having resonating charges have a significant role for agonist activity. The electrophilicity originates from the interelectronic exchange interaction, the LUMO energy and spherical shape are the key factors. The antagonist activity of diazoles is electronically a function of HOMONL energy and stereochemically a function of branching index and number of ring system. Localized charges have a negative contribution to the agonist activity, whereas the delocalized charges in diazoles and thiazoles increase the agonist behaviour
-
additional information
-
analysis of triazoles, diazoles, and thiazoles for their reversible inhibition and agonist activity. The chemical nature and position of substituents (chemical groups) on diazoles and triazole ring have different contributions to inhibition, while functional groups having resonating charges have a significant role for agonist activity. The electrophilicity originates from the interelectronic exchange interaction, the LUMO energy and spherical shape are the key factors. The antagonist activity of diazoles is electronically a function of HOMONL energy and stereochemically a function of branching index and number of ring system. Localized charges have a negative contribution to the agonist activity, whereas the delocalized charges in diazoles and thiazoles increase the agonist behaviour
-
additional information
structural requirements for azole chemicals with respect to the aromatase enzyme CYP19A1 activity. 21 structural alerts are associated with aromatase activity, identified from 326 azole-based drugs. Simple methylation of 1,3-thiazole, imidazole and xanthine scaffolds results inactivity while methylated 1,2,4-triazoles are active. Amination of 1,3-thiazole and benzothiazole, and arylation of 1,3-thiazole and diazole scaffolds are significant for activity. Agonist activity of thiazole and its derivatives can be tuned to inactive or antagonist under specific chemicals substitutions at different positions of the 1,3-thiazole ring. The activity of N-ethyl-1,2,4-triazole chemicals (mostly antagonist) can be increased by introducing a better electron donating group at the beta-carbon. Diazoles such as imidazolium ionic liquids and N-alkyl imidazoles have antagonist activity irrespective of the substitituents attached
-
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0.0016
(E)-2,4-dimethoxy-N-(4-(phenyldiazenyl)phenyl)benzenesulfonamide
Homo sapiens
pH not specified in the publication, temperature not specified in the publication
-
0.0079
(E)-4-cyano-N-(4-(phenyldiazenyl)phenyl)benzenesulfonamide
Homo sapiens
pH not specified in the publication, temperature not specified in the publication
-
0.0057
(E)-N-((1H-benzo[d]imidazole-2-yl)methyl)-2,4-dimethoxy-N-(4-(phenyldiazenyl)phenyl)benzenesulfonamide
Homo sapiens
pH not specified in the publication, temperature not specified in the publication
-
0.000006
1-(3-bromo-4-methoxybenzene-1-sulfonyl)-3-[(1H-imidazol-1-yl)methyl]piperidine
Homo sapiens
-
pH not specified in the publication, temperature not specified in the publication
0.000009
1-[3-(2-chloro-6-nitrophenyl)benzene-1-sulfonyl]-3-[(1H-imidazol-1-yl)methyl]piperidine
Homo sapiens
-
pH not specified in the publication, temperature not specified in the publication
0.0006
17beta,11alpha-dihydroxy-17alpha-methylandrosta-2-oxa-4-ene-3-one
Homo sapiens
pH 7.4, 37°C
-
0.00305
2-(pyridin-3-yl)-1H-indole
Homo sapiens
pH not specified in the publication, temperature not specified in the publication
0.00161
2-phenyl-1H-indole-3-carbonitrile
Homo sapiens
pH not specified in the publication, temperature not specified in the publication
0.000032
3-(4-(1H-benzo[d]imidazol-2-yl)phenyl)-6-(4-cyanophenyl)-7H-[1,2,4]triazole[3,4-b][1,3,4]thiadiazine
Homo sapiens
pH not specified in the publication, temperature not specified in the publication
-
0.00172
3-(4-(1H-benzo[d]imidazol-2-yl)phenyl)-6-(4-fluorophenyl)-7H-[1,2,4]triazole[3,4-b][1,3,4]thiadiazine
Homo sapiens
pH not specified in the publication, temperature not specified in the publication
-
0.00156
3-(4-(5-chloro-1H-benzo[d]imidazol-2-yl)phenyl)-6-(4-cyanophenyl)-7H-[1,2,4]triazole [3,4-b][1,3,4]thiadiazine
Homo sapiens
pH not specified in the publication, temperature not specified in the publication
-
0.00228
3-(4-(5-chloro-1H-benzo[d]imidazol-2-yl)phenyl)-6-(4-fluorophenyl)-7H-[1,2,4]triazole [3,4-b][1,3,4]thiadiazine
Homo sapiens
pH not specified in the publication, temperature not specified in the publication
-
0.000007
4-[3-[(1H-imidazol-1-yl)methyl]piperidine-1-sulfonyl]-2,1,3-benzothiadiazole
Homo sapiens
-
pH not specified in the publication, temperature not specified in the publication
0.009
5-nitro-2-phenyl-1H-indole
Homo sapiens
pH not specified in the publication, temperature not specified in the publication
0.000105
6alpha-allylandrost-4-ene-3,17-dione
Homo sapiens
pH 7.4, 37°C
-
0.000055
6alpha-allylandrosta-1,4-diene-3,17-dione
Homo sapiens
pH 7.4, 37°C
-
0.00017
6alpha-methylandrost-4-en-17-one
Homo sapiens
pH 7.4, 37°C
-
0.00006
6alpha-methylandrost-4-ene-3,17-dione
Homo sapiens
pH 7.4, 37°C
-
0.00006 - 0.00007
7,8-Benzoflavone
0.00011
7alpha-allyl-4-hydroxyandrost-4-ene-3,17-dione
Homo sapiens
pH 7.4, 37°C
-
0.000065
8-prenylnaringenin
Homo sapiens
-
pH not specified in the publication, temperature not specified in the publication
0.00005
exemestane
Homo sapiens
pH 7.4, 37°C
0.000042
formestane
Homo sapiens
pH 7.4, 37°C
0.00138
ganaxolone
Homo sapiens
pH 7.4, 37°C
-
0.081
isoxanthohumol
Homo sapiens
-
pH not specified in the publication, temperature not specified in the publication
0.000024
letrozole
Homo sapiens
pH not specified in the publication, temperature not specified in the publication
0.00081
oxandrolone
Homo sapiens
pH 7.4, 37°C
-
0.08
resveratrol
Homo sapiens
pH not specified in the publication, temperature not specified in the publication
0.000009
SYN 20028567
Homo sapiens
-
pH not specified in the publication, temperature not specified in the publication
0.0203
xanthohumol
Homo sapiens
-
pH not specified in the publication, temperature not specified in the publication
0.00006
7,8-Benzoflavone
Homo sapiens
-
substrate testosterone, pH 7.2, 37°C
0.00007
7,8-Benzoflavone
Homo sapiens
-
substrate androst-4-ene-3,17-dione, pH 7.2, 37°C
0.001
apigenin
Homo sapiens
-
substrate testosterone, pH 7.2, 37°C
0.0012
apigenin
Homo sapiens
-
substrate androst-4-ene-3,17-dione, pH 7.2, 37°C
0.0004
chrysin
Homo sapiens
-
substrate testosterone, pH 7.2, 37°C
0.0005
chrysin
Homo sapiens
-
substrate androst-4-ene-3,17-dione, pH 7.2, 37°C
0.005
flavanone
Homo sapiens
-
substrate testosterone, pH 7.2, 37°C
0.008
flavanone
Homo sapiens
-
substrate androst-4-ene-3,17-dione, pH 7.2, 37°C
0.005
flavone
Homo sapiens
-
substrate testosterone, pH 7.2, 37°C
0.008
flavone
Homo sapiens
-
substrate androst-4-ene-3,17-dione, pH 7.2, 37°C
0.01
quercetin
Homo sapiens
-
substrate testosterone, pH 7.2, 37°C
0.012
quercetin
Homo sapiens
-
substrate androst-4-ene-3,17-dione, pH 7.2, 37°C
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Bellino, F.; Holben, L.
Placental estrogen synthetase (aromatase): Evidence for phosphatase-dependent inactivation
Biochem. Biophys. Res. Commun.
162
498-504
1989
Homo sapiens
brenda
Kellis, J.T.; Nesnow, S.; Vickery, L.E.
Inhibition of aromatase cytochrome P-450 (estrogen synthetase) by derivatives of alpha-naphthoflavone
Biochem. Pharmacol.
35
2887-2891
1986
Homo sapiens
brenda
Osada, M.; Tawarayama, H.; Mori, K.
Estrogen synthesis in relation to gonadal development of Japanese scallop, Patinopecten yessoensis: Gonadal profile and immunolocalization of P450 aromatase and estrogen
Comp. Biochem. Physiol. B Biochem. Mol. Biol.
139
123-128
2004
Mizuhopecten yessoensis
brenda
Monteiro, R.; Becker, H.; Azevedo, I.; Calhau, C.
Effect of hop (Humulus lupulus L.) flavonoids on aromatase (estrogen synthase) activity
J. Agric. Food Chem.
54
2938-2943
2006
Homo sapiens, Homo sapiens ATCC HTB-144
brenda
Thompson, E.A.Jr.; Siiteri, P.K.
The involvement of human placental microsomal cytochrome P-450 in aromatization
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249
5373-5378
1974
Homo sapiens
brenda
Fishman, J.; Goto, J.
Mechanism of estrogen biosynthesis. Participation of multiple enzyme sites in placental aromatase hydroxylations
J. Biol. Chem.
256
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1981
Homo sapiens
brenda
Kellis, J.T.; Vickery, L.E.
Purification and characterization of human placental aromatase cytochrome P-450
J. Biol. Chem.
262
4413-20
1987
Homo sapiens
brenda
Sethumadhavan, K.; Bellino, F.
Human placental estrogen synthetase (aromatase). Effect of environment on the kinetics of protein-protein and substrate-protein interactions and the production of 19-oxygenated androgen intermediates in the purified reconstituted cytochrome P450 enzyme system
J. Steroid Biochem. Mol. Biol.
39
381-394
1991
Homo sapiens
brenda
Ghosh, D.; Griswold, J.; Erman, M.; Pangborn, W.
Structural basis for androgen specificity and oestrogen synthesis in human aromatase
Nature
457
219-223
2009
Homo sapiens (P11511), Homo sapiens
brenda
Yague, J.G.; Lavaque, E.; Carretero, J.; Azcoitia, I.; Garcia-Segura, L.M.
Aromatase, the enzyme responsible for estrogen biosynthesis, is expressed by human and rat glioblastomas
Neurosci. Lett.
368
279-284
2004
Homo sapiens, Rattus norvegicus
brenda
Ohlsson, C.; Hammarstedt, A.; Vandenput, L.; Saarinen, N.; Ryberg, H.; Windahl, S.H.; Farman, H.H.; Jansson, J.O.; Moverare-Skrtic, S.; Smith, U.; Zhang, F.P.; Poutanen, M.; Hedjazifar, S.; Sjoegren, K.
Increased adipose tissue aromatase activity improves insulin sensitivity and reduces adipose tissue inflammation in male mice
Am. J. Physiol. Endocrinol. Metab.
313
E450-E462
2017
Mus musculus (P28649), Mus musculus
brenda
Zuloaga, K.L.; Davis, C.M.; Zhang, W.; Alkayed, N.J.
Role of aromatase in sex-specific cerebrovascular endothelial function in mice
Am. J. Physiol. Heart Circ. Physiol.
306
H929-H937
2014
Mus musculus (P28649)
brenda
Mills, L.J.; Gutjahr-Gobell, R.E.; Zaroogian, G.E.; Horowitz, D.B.; Laws, S.C.
Modulation of aromatase activity as a mode of action for endocrine disrupting chemicals in a marine fish
Aquat. Toxicol.
147
140-150
2014
Tautogolabrus adspersus
brenda
Di Matteo, M.; Ammazzalorso, A.; Andreoli, F.; Caffa, I.; De Filippis, B.; Fantacuzzi, M.; Giampietro, L.; Maccallini, C.; Nencioni, A.; Parenti, M.D.; Soncini, D.; Del Rio, A.; Amoroso, R.
Synthesis and biological characterization of 3-(imidazol-1-ylmethyl)piperidine sulfonamides as aromatase inhibitors
Bioorg. Med. Chem. Lett.
26
3192-3194
2016
Homo sapiens
brenda
Prior, A.M.; Yu, X.; Park, E.J.; Kondratyuk, T.P.; Lin, Y.; Pezzuto, J.M.; Sun, D.
Structure-activity relationships and docking studies of synthetic 2-arylindole derivatives determined with aromatase and quinone reductase 1
Bioorg. Med. Chem. Lett.
27
5393-5399
2017
Homo sapiens (P11511)
brenda
Sun, C.; Liu, Y.; Liu, Y.; Zhao, M.; Zhai, J.; Hao, P.; Wang, Y.; Ji, Y.
Characterization of aromatase expression in the spinal cord of an animal model of familial ALS
Brain Res. Bull.
132
180-189
2017
Mus musculus (P28649), Mus musculus
brenda
Caruso, C.C.; Breton, T.S.; Berlinsky, D.L.
The effects of temperature on ovarian aromatase (cyp19a1a) expression and sex differentiation in summer flounder (Paralichthys dentatus)
Fish Physiol. Biochem.
42
795-805
2016
Paralichthys dentatus (A0A0H4KB14), Paralichthys dentatus
brenda
Parsley, L.M.; Wapstra, E.; Jones, S.M.
Placental and embryonic tissues exhibit aromatase activity in the viviparous lizard Niveoscincus metallicus
Gen. Comp. Endocrinol.
200
61-66
2014
Carinascincus metallicus
brenda
Chaube, R.; Rawat, A.; Joy, K.P.
Molecular cloning and characterization of brain and ovarian cytochrome P450 aromatase genes in the catfish Heteropneustes fossilis Sex, tissue and seasonal variation in, and effects of gonadotropin on gene expression
Gen. Comp. Endocrinol.
221
120-133
2015
Heteropneustes fossilis (A0A068CIW9), Heteropneustes fossilis (A0A068CLX6), Heteropneustes fossilis
brenda
Ramallo, M.R.; Morandini, L.; Birba, A.; Somoza, G.M.; Pandolfi, M.
From molecule to behavior Brain aromatase (cyp19a1b) characterization, expression analysis and its relation with social status and male agonistic behavior in a Neotropical cichlid fish
Horm. Behav.
89
176-188
2017
Cichlasoma dimerus (M1GNQ2), Cichlasoma dimerus
brenda
Aggarwal, N.; Goswami, S.V.; Khandelwal, P.; Sehgal, N.
Aromatase activity in brain and ovary seasonal variations correlated with circannual gonadal cycle in the catfish, Heteropneustes fossilis
Indian J. Exp. Biol.
52
527-537
2014
Heteropneustes fossilis
brenda
Di Nardo, G.; Breitner, M.; Bandino, A.; Ghosh, D.; Jennings, G.K.; Hackett, J.C.; Gilardi, G.
Evidence for an elevated aspartate pK(a) in the active site of human aromatase
J. Biol. Chem.
290
1186-1196
2015
Homo sapiens (P11511), Homo sapiens
brenda
Aversa, A.; Fittipaldi, S.; Bimonte, V.M.; Wannenes, F.; Papa, V.; Francomano, D.; Greco, E.A.; Lenzi, A.; Migliaccio, S.
Tadalafil modulates aromatase activity and androgen receptor expression in a human osteoblastic cell in vitro model
J. Endocrinol. Invest.
39
199-205
2016
Homo sapiens (P11511), Homo sapiens
brenda
Magistrato, A.; Sgrignani, J.; Krause, R.; Cavalli, A.
Single or multiple access channels to the CYP450s active site? An answer from free energy simulations of the human aromatase enzyme
J. Phys. Chem. Lett.
8
2036-2042
2017
Homo sapiens (P11511), Homo sapiens
brenda
Martin, L.L.; Holien, J.K.; Mizrachi, D.; Corbin, C.J.; Conley, A.J.; Parker, M.W.; Rodgers, R.J.
Evolutionary comparisons predict that dimerization of human cytochrome P450 aromatase increases its enzymatic activity and efficiency
J. Steroid Biochem. Mol. Biol.
154
294-301
2015
Homo sapiens (P11511), Sus scrofa (P79304)
brenda
Baravalle, R.; Valetti, F.; Catucci, G.; Gambarotta, G.; Chiesa, M.; Maurelli, S.; Giamello, E.; Barone, I.; Catalano, S.; Ando, S.; Di Nardo, G.; Gilardi, G.
Effect of sildenafil on human aromatase activity From in vitro structural analysis to catalysis and inhibition in cells
J. Steroid Biochem. Mol. Biol.
165
438-447
2017
Homo sapiens (P11511), Homo sapiens
brenda
Bouchoucha, N.; Samara-Boustani, D.; Pandey, A.V.; Bony-Trifunovic, H.; Hofer, G.; Aigrain, Y.; Polak, M.; Flueck, C.E.
Characterization of a novel CYP19A1 (aromatase) R192H mutation causing virilization of a 46,XX newborn, undervirilization of the 46,XY brother, but no virilization of the mother during pregnancies
Mol. Cell. Endocrinol.
390
8-17
2014
Homo sapiens (P11511), Homo sapiens
brenda
Hudon Thibeault, A.A.; Vaillancourt, C.; Sanderson, J.T.
Profile of CYP19A1 mRNA expression and aromatase activity during syncytialization of primary human villous trophoblast cells at term
Biochimie
148
12-17
2018
Homo sapiens (P11511), Homo sapiens
brenda
Di Nardo, G.; Di Venere, A.; Zhang, C.; Nicolai, E.; Castrignano, S.; Di Paola, L.; Gilardi, G.; Mei, G.
Polymorphism on human aromatase affects protein dynamics and substrate binding spectroscopic evidence
Biol. Direct
16
008
2021
Homo sapiens (P11511), Homo sapiens
brenda
Giampietro, L.; Gallorini, M.; Gambacorta, N.; Ammazzalorso, A.; De Filippis, B.; Della Valle, A.; Fantacuzzi, M.; Maccallini, C.; Mollica, A.; Cataldi, A.; Nicolotti, O.; Amoroso, R.
Synthesis, structure-activity relationships and molecular docking studies of phenyldiazenyl sulfonamides as aromatase inhibitors
Eur. J. Med. Chem.
224
113737
2021
Homo sapiens (P11511), Homo sapiens
brenda
Tuzuner, M.B.; Ozturk, T.; Ilvan, S.; Turna, H.; Yurdun, T.; Yilmaz-Aydogan, H.; Ozturk, O.
Local aromatase activity alterations in breast cancer tissues A potential way of decision support for clinicians
Exp. Mol. Pathol.
118
104574
2021
Homo sapiens (P11511), Homo sapiens
brenda
Rahman, M.; Thomas, P.
Molecular characterization and expression of cytochrome P450 aromatase in Atlantic croaker brain regulation by antioxidant status and nitric oxide synthase during hypoxia stress
Front. Physiol.
12
720200
2021
Micropogonias undulatus (Q3LS70), Micropogonias undulatus
brenda
Guan, Y.; Lu, Y.; Wang, Y.; Xue, K.
Let-7g inhibits synthesis of estradiol by downregulating activity of aromatase in JEG3 cells
J. Cell. Biochem.
120
1819-1826
2019
Homo sapiens (P11511), Homo sapiens
brenda
Zarate-Perez, F.; Velazquez-Fernandez, J.B.; Jennings, G.K.; Shock, L.S.; Lyons, C.E.; Hackett, J.C.
Biophysical characterization of Aptenodytes forsteri cytochrome P450 aromatase
J. Inorg. Biochem.
184
79-87
2018
Aptenodytes forsteri (A0A087RFY9), Aptenodytes forsteri
brenda
Roleira, F.M.F.; Varela, C.; Amaral, C.; Costa, S.C.; Correia-da-Silva, G.; Moraca, F.; Costa, G.; Alcaro, S.; Teixeira, N.A.A.; Tavares da Silva, E.J.
C-6alpha- vs C-7alpha-substituted steroidal aromatase inhibitors which is better? synthesis, biochemical evaluation, docking studies, and structure-activity relationships
J. Med. Chem.
62
3636-3657
2019
Homo sapiens (P11511)
brenda
Parween, S.; DiNardo, G.; Baj, F.; Zhang, C.; Gilardi, G.; Pandey, A.V.
Differential effects of variations in human P450 oxidoreductase on the aromatase activity of CYP19A1 polymorphisms R264C and R264H
J. Steroid Biochem. Mol. Biol.
196
105507
2020
Homo sapiens (P11511), Homo sapiens
brenda
Williams, G.P.; Darbre, P.D.
Low-dose environmental endocrine disruptors, increase aromatase activity, estradiol biosynthesis and cell proliferation in human breast cells
Mol. Cell. Endocrinol.
486
55-64
2019
Homo sapiens (P11511), Homo sapiens
brenda
Acar Cevik, U.; Kaya Cavusoglu, B.; Saglik, B.N.; Osmaniye, D.; Levent, S.; Ilgin, S.; Oezkay, Y.; Kaplancikli, Z.A.
Synthesis, docking studies and biological activity of new benzimidazole-triazolothiadiazine derivatives as aromatase inhibitor
Molecules
25
1642
2020
Homo sapiens (P11511), Homo sapiens
brenda
Chayawan, C.; Toma, C.; Benfenati, E.; Caballero Alfonso, A.
Towards an understanding of the mode of action of human aromatase activity for azoles through quantum chemical descriptors-based regression and structure activity relationship modeling analysis
Molecules
25
739
2020
Homo sapiens (P11511), Homo sapiens
brenda
Siddiqui, M.; Atia-tul-Waha, A.; Naveed Shaikh, N.; Baydoun, E.; Atta-ur-Rahma, A.; Choudhary, M.
Biocatalytic transformation of steroidal drugs oxandrolone and ganaxolone, and aromatase inhibitory activity of transformed products
Phytochem. Lett.
44
137-141
2021
Homo sapiens (P11511)
-
brenda
Caballero Alfonso, A.Y.; Mora Lagares, L.; Novic, M.; Benfenati, E.; Kumar, A.; Chayawan, A.
Exploration of structural requirements for azole chemicals towards human aromatase CYP19A1 activity Classification modeling, structure-activity relationships and read-across study
Toxicol. In Vitro
81
105332
2022
Homo sapiens (P11511)
brenda
Doering, J.A.; Villeneuve, D.L.; Fay, K.A.; Randolph, E.C.; Jensen, K.M.; Kahl, M.D.; LaLone, C.A.; Ankley, G.T.
Differential sensitivity to in vitro inhibition of cytochrome P450 aromatase (CYP19) activity among 18 freshwater fishes
Toxicol. Sci.
170
394-403
2019
Esox lucius, Oncorhynchus mykiss, Pimephales promelas, Catostomus commersonii, Polyodon spathula
brenda