1.14.14.14: aromatase
This is an abbreviated version!
For detailed information about aromatase, go to the full flat file.
Word Map on EC 1.14.14.14
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1.14.14.14
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estrogen
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women
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androgen
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steroid
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postmenopausal
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ovarian
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tamoxifen
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ovary
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progesterone
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letrozole
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granulosa
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follicle
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gonad
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anastrozole
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receptor-positive
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fsh
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steroidogenic
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exemestane
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androstenedione
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gonadotropin
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steroidogenesis
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endometrial
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lutein
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follicular
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testicular
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antiestrogens
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fulvestrant
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er-positive
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nonsteroidal
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endometriosis
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neoadjuvant
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preoptic
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third-generation
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hormone-dependent
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follicle-stimulating
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gnrh
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estrogen-dependent
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oestradiol
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dihydrotestosterone
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premenopausal
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mastectomy
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arthralgia
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17beta-hydroxysteroid
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everolimus
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5alpha-reductase
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cyp17a1
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raloxifene
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medicine
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virilization
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progestin
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her2-negative
- 1.14.14.14
- estrogen
- women
- androgen
- steroid
-
postmenopausal
- ovarian
- tamoxifen
- ovary
- progesterone
- letrozole
-
granulosa
- follicle
- gonad
- anastrozole
-
receptor-positive
- fsh
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steroidogenic
- exemestane
- androstenedione
- gonadotropin
- steroidogenesis
- endometrial
- lutein
- follicular
- testicular
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antiestrogens
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fulvestrant
-
er-positive
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nonsteroidal
- endometriosis
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neoadjuvant
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preoptic
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third-generation
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hormone-dependent
-
follicle-stimulating
- gnrh
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estrogen-dependent
- oestradiol
- dihydrotestosterone
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premenopausal
-
mastectomy
- arthralgia
-
17beta-hydroxysteroid
-
everolimus
-
5alpha-reductase
- cyp17a1
- raloxifene
- medicine
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virilization
- progestin
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her2-negative
Reaction
Synonyms
AROM, Cyp19a, CYP19A1, Cyp19a1a, Cyp19a1b, Cyp19A3, cytochrome P450 aromatase, P450arom
ECTree
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Inhibitors
Inhibitors on EC 1.14.14.14 - aromatase
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(E)-2,4-dimethoxy-N-(4-(phenyldiazenyl)phenyl)benzenesulfonamide
not effective on HFF-1 cells
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(E)-4-cyano-N-(4-(phenyldiazenyl)phenyl)benzenesulfonamide
not effective on HFF-1 cells
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(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
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1,4,6-androstatriene-3,17-dione
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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
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1-[3-(2-chloro-6-nitrophenyl)benzene-1-sulfonyl]-3-[(1H-imidazol-1-yl)methyl]piperidine
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19-nortestosterone
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competitive inhibitor of both aromatization and cytochrome P450 binding of androst-4-ene-3,17-dione
3-(4-(1H-benzo[d]imidazol-2-yl)phenyl)-6-(4-cyanophenyl)-7H-[1,2,4]triazole[3,4-b][1,3,4]thiadiazine
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3-(4-(1H-benzo[d]imidazol-2-yl)phenyl)-6-(4-fluorophenyl)-7H-[1,2,4]triazole[3,4-b][1,3,4]thiadiazine
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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
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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
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4-[3-[(1H-imidazol-1-yl)methyl]piperidine-1-sulfonyl]-2,1,3-benzothiadiazole
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5-nitro-2-phenyl-1H-indole
compound is inhibitory toward aromatase and induces quinone reductase 1
6alpha-allylandrosta-1,4-diene-3,17-dione
competitive, irreversible, at 0.010 mM 99.2% inhibition of activity in MCF-7aro cells
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6alpha-methylandrost-4-ene-3,17-dione
competitive, reversible, at 0.010 mM 98.5% inhibition of activity in MCF-7aro cells
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7,8-Benzoflavone
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competitive inhibitor, induces spectral changes in the aromatase cytochrome P450
8-prenylnaringenin
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flavonoid isolated from hop, inhibits enzyme activity, no effect on enzyme expression
androst-4-ene-3,17-dione
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competitive inhibitor of both aromatization and cytochrome P450 binding of 19-nortestosterone
chrysin
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competitive inhibitor, induces spectral changes in the aromatase cytochrome P450
isoxanthohumol
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flavonoid isolated from hop, inhibits enzyme activity, no effect on enzyme expression
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
xanthohumol
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flavonoid isolated from hop, inhibits enzyme activity, no effect on enzyme expression
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competitive with substrates androst-4-ene-3,17-dione and 19-oxoandrost-4-ene-3,17-dione
19-hydroxyandrost-4-ene-3,17-dione
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competitively inhibits the formation of 19-hydroxyandrost-4-ene-3,17-dione and estrogen
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competitive with substrates androst-4-ene-3,17-dione and 19-hydroxyandrost-4-ene-3,17-dione
19-oxoandrost-4-ene-3,17-dione
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competitively inhibits the formation of 19-oxoandrost-4-ene-3,17-dione and estrogen
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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treatment with alkaline phosphatase results in loss of activity, as well as incubation in phosphate-free buffer
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additional information
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lager beer, alcohol-free beer, stout beer, and xanthohumol-rich stout beer significantly decrease aromatase activity
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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
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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
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additional information
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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
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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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