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Information on EC 1.14.14.14 - aromatase
for references in articles please use BRENDA:EC1.14.14.14
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EC Tree 1 Oxidoreductases
1.14 Acting on paired donors, with incorporation or reduction of molecular oxygen
1.14.14 With reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen into the other donor
1.14.14.14 aromatase
IUBMB Comments
A cytochrome P-450. The enzyme catalyses three sequential hydroxylations of the androgens androst-4-ene-3,17-dione and testosterone, resulting in their aromatization and forming the estrogens estrone and 17β-estradiol, respectively. The direct electron donor to the enzyme is EC 1.6.2.4, NADPH—hemoprotein reductase.
The enzyme appears in viruses and cellular organisms
- 1.14.14.14
- estrogen
- women
- androgen
- steroid
-
postmenopausal
- ovarian
- tamoxifen
- ovary
- progesterone
- letrozole
-
granulosa
- follicle
- gonad
- anastrozole
-
receptor-positive
- fsh
-
steroidogenic
- exemestane
- androstenedione
- gonadotropin
- steroidogenesis
- endometrial
- lutein
- follicular
- testicular
-
antiestrogens
-
fulvestrant
-
er-positive
-
nonsteroidal
- endometriosis
-
neoadjuvant
-
preoptic
-
third-generation
-
hormone-dependent
-
follicle-stimulating
- gnrh
-
estrogen-dependent
- oestradiol
- dihydrotestosterone
-
premenopausal
-
mastectomy
- arthralgia
-
17beta-hydroxysteroid
-
everolimus
-
5alpha-reductase
- cyp17a1
- raloxifene
- medicine
-
virilization
- progestin
-
her2-negative
Reaction Schemes
show+
3
+
3
=
+
+
4
+
3
+
3
+
3
=
+
+
4
+
3
Synonyms
aromatase, cyp19a1, cyp19a1a, cyp19a, cyp19a1b, cyp19a3, more
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
CYP19A1
Cyp19a1a
cytochrome P450 aromatase
CYP19A1
-
-
-
-
CYP19A1
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
19-hydroxyandrost-4-ene-3,17-dione + O2 + [reduced NADPH-hemoprotein reductase] = 19-oxo-androst-4-ene-3,17-dione + 2 H2O + [oxidized NADPH-hemoprotein reductase]
(2b)
-
-
-
19-hydroxytestosterone + O2 + [reduced NADPH-hemoprotein reductase] = 19-oxotestosterone + 2 H2O + [oxidized NADPH-hemoprotein reductase]
(1b)
-
-
-
19-oxoandrost-4-ene-3,17-dione + O2 + [reduced NADPH-hemoprotein reductase] = estrone + formate + H2O + [oxidized NADPH-hemoprotein reductase]
catalytic reaction mechanism, detailed overview
-
-
-
19-oxotestosterone + O2 + [reduced NADPH-hemoprotein reductase] = 17beta-estradiol + formate + H2O + [oxidized NADPH-hemoprotein reductase]
(1c)
-
-
-
androst-4-ene-3,17-dione + 3 O2 + 3 [reduced NADPH-hemoprotein reductase] = estrone + formate + 4 H2O + 3 [oxidized NADPH-hemoprotein reductase]
(2)
-
-
-
androst-4-ene-3,17-dione + O2 + [reduced NADPH-hemoprotein reductase] = 19-hydroxyandrost-4-ene-3,17-dione + H2O + [oxidized NADPH-hemoprotein reductase]
(2a)
-
-
-
testosterone + 3 O2 + 3 [reduced NADPH-hemoprotein reductase] = 17beta-estradiol + formate + 4 H2O + 3 [oxidized NADPH-hemoprotein reductase]
(1)
-
-
-
testosterone + O2 + [reduced NADPH-hemoprotein reductase] = 19-hydroxytestosterone + H2O + [oxidized NADPH-hemoprotein reductase]
(1a)
-
-
-
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SYSTEMATIC NAME
IUBMB Comments
testosterone monooxygenase (17beta-estradiol-forming)
A cytochrome P-450. The enzyme catalyses three sequential hydroxylations of the androgens androst-4-ene-3,17-dione and testosterone, resulting in their aromatization and forming the estrogens estrone and 17beta-estradiol, respectively. The direct electron donor to the enzyme is EC 1.6.2.4, NADPH---hemoprotein reductase.
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
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
-
Substrates: overall reaction
Products: -
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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
-
Substrates: -
Products: -
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?
7-methoxy-4-trifluoromethyl coumarin + H2O + oxidized flavoprotein
? + O2 + reduced flavoprotein
-
Substrates: -
Products: -
Products: -
?
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
-
Substrates: -
Products: -
Products: -
?
testosterone + 3 O2 + 3 reduced flavoproteins
17beta-estradiol + formate + 4 H2O + 3 oxidized flavoproteins
19-hydroxyandrost-4-ene-3,17-dione + O2 + a reduced flavoprotein
19-oxo-androst-4-ene-3,17-dione + 2 H2O + an oxidized flavoprotein
Substrates: -
Products: -
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19-hydroxyandrost-4-ene-3,17-dione + O2 + a reduced flavoprotein
19-oxo-androst-4-ene-3,17-dione + 2 H2O + an oxidized flavoprotein
-
Substrates: -
Products: -
Products: -
?
androst-4-ene-3,17-dione + 3 O2 + 3 reduced flavoproteins
estrone + formate + 4 H2O + 3 oxidized flavoproteins
Substrates: -
Products: -
Products: -
?
androst-4-ene-3,17-dione + 3 O2 + 3 reduced flavoproteins
estrone + formate + 4 H2O + 3 oxidized flavoproteins
-
Substrates: -
Products: -
Products: -
?
androst-4-ene-3,17-dione + 3 O2 + 3 reduced flavoproteins
estrone + formate + 4 H2O + 3 oxidized flavoproteins
Substrates: -
Products: -
Products: -
?
androst-4-ene-3,17-dione + 3 O2 + 3 reduced flavoproteins
estrone + formate + 4 H2O + 3 oxidized flavoproteins
-
Substrates: -
Products: -
Products: -
?
androst-4-ene-3,17-dione + 3 O2 + 3 reduced flavoproteins
estrone + formate + 4 H2O + 3 oxidized flavoproteins
Substrates: -
Products: -
Products: -
?
androst-4-ene-3,17-dione + 3 O2 + 3 reduced flavoproteins
estrone + formate + 4 H2O + 3 oxidized flavoproteins
-
Substrates: -
Products: -
Products: -
?
androst-4-ene-3,17-dione + 3 O2 + 3 reduced flavoproteins
estrone + formate + 4 H2O + 3 oxidized flavoproteins
-
Substrates: -
Products: overall reaction
Products: overall reaction
?
androst-4-ene-3,17-dione + 3 O2 + 3 reduced flavoproteins
estrone + formate + 4 H2O + 3 oxidized flavoproteins
-
Substrates: overall reaction
Products: -
Products: -
?
androst-4-ene-3,17-dione + 3 O2 + 3 reduced flavoproteins
estrone + formate + 4 H2O + 3 oxidized flavoproteins
Substrates: -
Products: -
Products: -
?
testosterone + 3 O2 + 3 reduced flavoproteins
17beta-estradiol + formate + 4 H2O + 3 oxidized flavoproteins
Substrates: -
Products: -
Products: -
?
testosterone + 3 O2 + 3 reduced flavoproteins
17beta-estradiol + formate + 4 H2O + 3 oxidized flavoproteins
-
Substrates: -
Products: -
Products: -
?
testosterone + 3 O2 + 3 reduced flavoproteins
17beta-estradiol + formate + 4 H2O + 3 oxidized flavoproteins
-
Substrates: overall reaction
Products: -
Products: -
?
additional information
?
-
Substrates: androstenedione is the preferred substrate, the affinity of the intermediates progressively decrease with increased oxidation
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additional information
?
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Substrates: androstenedione is the preferred substrate, the affinity of the intermediates progressively decrease with increased oxidation
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additional information
?
-
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Substrates: 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
Products: -
Products: -
?
additional information
?
-
-
Substrates: 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
Products: -
Products: -
?
additional information
?
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Substrates: 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
Products: -
Products: -
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
androst-4-ene-3,17-dione + 3 O2 + 3 reduced flavoproteins
estrone + formate + 4 H2O + 3 oxidized flavoproteins
-
Substrates: overall reaction
Products: -
Products: -
?
testosterone + 3 O2 + 3 reduced flavoproteins
17beta-estradiol + formate + 4 H2O + 3 oxidized flavoproteins
-
Substrates: overall reaction
Products: -
Products: -
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
cytochrome P450
-
inhibitors 7,8-benzoflavone and chrysin induce spectral changes in the aromatase cytochrome P450
-
cytochrome P450
-
specific content of 11.5 nmol of P450/mg of protein. Enzyme displays spectroscopic properties typical of the ferric and ferrous forms of cytochrome P-450
-
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
(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
-
-
19-nortestosterone
-
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
-
-
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-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-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
8-prenylnaringenin
-
flavonoid isolated from hop, inhibits enzyme activity, no effect on enzyme expression
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
isoxanthohumol
-
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
-
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
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
-
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
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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
-
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
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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
-
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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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0002
androst-4-ene-3,17-dione
pH 7.4, temperature not specified in the publication
additional information
androst-4-ene-3,17-dione
the Km values increase 1.5fold from pH 6.5 to 7.4similar to the Kd values, temperature not specified in the publication
additional information
androst-4-ene-3,17-dione
-
the Km values increase 1.5fold from pH 6.5 to 7.4similar to the Kd values, temperature not specified in the publication
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.02
androst-4-ene-3,17-dione
pH 7.4, temperature not specified in the publication
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Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.00038
19-hydroxyandrost-4-ene-3,17-dione
-
substrate 19-oxoandrost-4-ene-3,17-dione, pH 7.0, 37°C
0.00045
19-hydroxyandrost-4-ene-3,17-dione
-
substrate androst-4-ene-3,17-dione, pH 7.0, 37°C
0.0015
19-oxoandrost-4-ene-3,17-dione
-
substrate 19-hydroxyandrost-4-ene-3,17-dione, pH 7.0, 37°C
0.003
19-oxoandrost-4-ene-3,17-dione
-
substrate androst-4-ene-3,17-dione, pH 7.0, 37°C
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IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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
0.000065
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
0.000024
letrozole
Homo sapiens
pH not specified in the publication, temperature not specified in the publication
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
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
additional information
androstenedione binding is pH-dependent. The apparent pKa for Asp309 is 8.2, and the residue is protonated at physiological pH. A D309N mutant binds androstenedione across the entire pH range studied
additional information
-
androstenedione binding is pH-dependent. The apparent pKa for Asp309 is 8.2, and the residue is protonated at physiological pH. A D309N mutant binds androstenedione across the entire pH range studied
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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SOURCE TISSUE
ORGANISM