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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
?
-
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
-
overall reaction
-
-
?
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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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
-
-
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
-
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
7,8-Benzoflavone
-
competitive inhibitor, induces spectral changes in the aromatase cytochrome P450
8-prenylnaringenin
-
flavonoid isolated from hop, inhibits enzyme activity, no effect on enzyme expression
Aminoglutethimide
-
0.005 mM, 54% residual activity
anastrozole
azole inhibitor, binding is independent of pH
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
exemestane
steroidal inhibitor, binding is dependent of pH
isoxanthohumol
-
flavonoid isolated from hop, inhibits enzyme activity, no effect on enzyme expression
KCN
-
5 mM, 80% residual activity
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
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
-
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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
0.00305
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
0.000007
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
0.00006 - 0.00007
7,8-Benzoflavone
0.000065
8-prenylnaringenin
Homo sapiens
-
pH not specified in the publication, temperature not specified in the publication
0.081
isoxanthohumol
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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-
maternal ovaries and adrenals maintain high aromatase activity throughout gestation
brenda
-
cell line expresses aromatase mRNA and shows a cytoplasmic pattern of aromatase immunoreactivity. In addition, the cell line expresses estrogen receptor alpha
brenda
-
aromatase activity in the developing brains and gonads of embryos is comparable with measurements in oviparous reptiles. Aromatase activity in the embryonic gonads is low at embryonic stage 29-34, but increases significantly at mid-development and then remains high in late stage embryos
brenda
-
-
brenda
-
in the female, activity is detecable throughout the year
brenda
-
brenda
-
cell line expresses aromatase mRNA and shows a cytoplasmic pattern of aromatase immunoreactivity. In addition, the cell line expresses estrogen receptor alpha
brenda
-
cell line expresses aromatase mRNA and shows a cytoplasmic pattern of aromatase immunoreactivity. In addition, the cell line expresses estrogen receptor alpha
brenda
Cyp19a1b is solely detected at putative radial glial cells of the forebrain, close to the brain ventricles
brenda
high transcript abundance in the female brain, followed by gonads, liver, gill, kidney and muscle
brenda
high transcript abundance in the ovary and female brain, followed by the testis and male brain, and female liver and muscle
brenda
higher aromatase expression in female compared with male cerebral vessels
brenda
-
male brain aromatase activity is signficantly increased by treatments with estradiol or ethynylestradiol while female brain aromatase activity is unaffected
brenda
high transcript abundance in the female brain, followed by gonads, liver, gill, kidney and muscle
brenda
-
-
brenda
-
trophoblastic tumor cell of placenta
brenda
-
trophoblastic tumor cell of placenta
-
brenda
high transcript abundance in the female brain, followed by gonads, liver, gill, kidney and muscle
brenda
high transcript abundance in the ovary and female brain, followed by the testis and male brain, and female liver and muscle
brenda
high transcript abundance in the female brain, followed by gonads, liver, gill, kidney and muscle
brenda
high transcript abundance in the ovary and female brain, followed by the testis and male brain, and female liver and muscle
brenda
-
maternal ovaries and adrenals maintain high aromatase activity throughout gestation
brenda
-
activity is found only during vitellogenesis. At the completion of vitellogenesis, ovarian aromatase activity declines sharply resulting in elevation of plasma testosterone levels
brenda
highest signal intensity
brenda
-
-
brenda
-
increases in aromatase activities of the ovary and testis precede the onset of the ovarian and testicular development. Aromatase activities reach the highest level at the growing stage in February and the mature stage in March, and show a striking decrease at the spawning stage in April. Contents of ovarian and testicular estradiol-17beta change similarly to the profile of aromatase activities in the ovary and testis, although estrone shows no change
brenda
-
brenda
-
ovarian aromatase activity is significantly decreased by treatments with estradiol or ethynylestradiol
brenda
-
during the early phases of embryonic development, placental aromatase activity is comparable to that in maternal ovaries, but declines significantly at progressive stages of gestation
brenda
-
-
brenda
-
brenda
high transcript abundance in the ovary and female brain, followed by the testis and male brain, and female liver and muscle
brenda
-
immunoreactivities against aromatase and estradiol-17beta are detected in the cells along the inside of the acinar wall of the testis
brenda
additional information

brain aromatase expression does not differ between types of males, but pituitary Cyp19a1b expression levels positively correlate with the index of agonistic behavior
brenda
additional information
-
brain aromatase expression does not differ between types of males, but pituitary Cyp19a1b expression levels positively correlate with the index of agonistic behavior
brenda
additional information
Cyp19a1b expression is higher in females than males
brenda
additional information
Cyp19a1b expression is higher in females than males
brenda
additional information
-
Cyp19a1b expression is higher in females than males
brenda
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Placental estrogen synthetase (aromatase): Evidence for phosphatase-dependent inactivation
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162
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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
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35
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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
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Mizuhopecten yessoensis
brenda
Monteiro, R.; Becker, H.; Azevedo, I.; Calhau, C.
Effect of hop (Humulus lupulus L.) flavonoids on aromatase (estrogen synthase) activity
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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
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Homo sapiens
brenda
Fishman, J.; Goto, J.
Mechanism of estrogen biosynthesis. Participation of multiple enzyme sites in placental aromatase hydroxylations
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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
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262
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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
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39
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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
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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
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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
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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