Information on EC 1.14.14.14 - aromatase

New: Word Map on EC 1.14.14.14
Please wait a moment until all data is loaded. This message will disappear when all data is loaded.
Specify your search results
Mark a special word or phrase in this record:
Search Reference ID:
Select one or more organisms in this record:
Show additional data
Do not include text mining results
Include (text mining) results (more...)
Include results (AMENDA + additional results, but less precise; more...)


The expected taxonomic range for this enzyme is: Coelomata

EC NUMBER
COMMENTARY hide
1.14.14.14
-
RECOMMENDED NAME
GeneOntology No.
aromatase
-
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
19-hydroxyandrost-4-ene-3,17-dione + O2 + a reduced flavoprotein = 19-oxo-androst-4-ene-3,17-dione + 2 H2O + an oxidized flavoprotein
show the reaction diagram
(2b)
-
-
-
19-hydroxytestosterone + O2 + a reduced flavoprotein = 19-oxotestosterone + 2 H2O + an oxidized flavoprotein
show the reaction diagram
(1b)
-
-
-
19-oxoandrost-4-ene-3,17-dione + O2 + a reduced flavoprotein = estrone + formate + H2O + an oxidized flavoprotein
show the reaction diagram
catalytic reaction mechanism, detailed overview
-
-
-
19-oxotestosterone + O2 + a reduced flavoprotein = 17beta-estradiol + formate + H2O + an oxidized flavoprotein
show the reaction diagram
(1c)
-
-
-
androst-4-ene-3,17-dione + 3 O2 + 3 reduced flavoproteins = estrone + formate + 4 H2O + 3 oxidized flavoproteins
show the reaction diagram
(2)
-
-
-
androst-4-ene-3,17-dione + O2 + a reduced flavoprotein = 19-hydroxyandrost-4-ene-3,17-dione + H2O + an oxidized flavoprotein
show the reaction diagram
(2a)
-
-
-
testosterone + 3 O2 + 3 reduced flavoproteins = 17beta-estradiol + formate + 4 H2O + 3 oxidized flavoproteins
show the reaction diagram
(1)
-
-
-
testosterone + O2 + a reduced flavoprotein = 19-hydroxytestosterone + H2O + an oxidized flavoprotein
show the reaction diagram
(1a)
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Metabolic pathways
-
-
Steroid hormone biosynthesis
-
-
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.
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
Homo sapiens ATCC HTB-144
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
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
show the reaction diagram
-
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
show the reaction diagram
-
-
-
-
?
19-oxoandrost-4-ene-3,17-dione + O2 + a reduced flavoprotein
estrone + formate + H2O + an oxidized flavoprotein
show the reaction diagram
-
-
-
-
?
androst-4-ene-3,17-dione + 3 O2 + 3 reduced flavoproteins
estrone + formate + 4 H2O + 3 oxidized flavoproteins
show the reaction diagram
androst-4-ene-3,17-dione + O2 + a reduced flavoprotein
19-hydroxyandrost-4-ene-3,17-dione + H2O + an oxidized flavoprotein
show the reaction diagram
-
-
-
-
?
testosterone + 3 O2 + 3 reduced flavoproteins
17beta-estradiol + formate + 4 H2O + 3 oxidized flavoproteins
show the reaction diagram
-
overall reaction
-
-
?
additional information
?
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
androst-4-ene-3,17-dione + 3 O2 + 3 reduced flavoproteins
estrone + formate + 4 H2O + 3 oxidized flavoproteins
show the reaction diagram
-
overall reaction
-
-
?
testosterone + 3 O2 + 3 reduced flavoproteins
17beta-estradiol + formate + 4 H2O + 3 oxidized flavoproteins
show the reaction diagram
-
overall reaction
-
-
?
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
cytochrome P450
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
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
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
androst-4-ene-3,17-dione
-
competitive inhibitor of both aromatization and cytochrome P450 binding of 19-nortestosterone
apigenin
-
-
chrysin
-
competitive inhibitor, induces spectral changes in the aromatase cytochrome P450
diethylaminoethyl-2,2-diphenylvalerate
-
0.05 mM, 64% residual activity
flavanone
-
-
flavone
-
-
isoxanthohumol
-
flavonoid isolated from hop, inhibits enzyme activity, no effect on enzyme expression
KCN
-
5 mM, 80% residual activity
quercetin
-
-
xanthohumol
-
flavonoid isolated from hop, inhibits enzyme activity, no effect on enzyme expression
additional information
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.058
16alpha-hydroxytestosterone
-
pH 7.2, 37C
0.00006
androst-4-ene-3,17-dione
-
pH 7.2, 37C
0.00021
testosterone
-
pH 7.2, 37C
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.00038 - 0.00045
19-hydroxyandrost-4-ene-3,17-dione
0.0015 - 0.003
19-oxoandrost-4-ene-3,17-dione
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
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
0.001 - 0.0012
apigenin
0.0004 - 0.0005
chrysin
0.005 - 0.008
flavanone
0.008
flavone
Homo sapiens
-
substrate androst-4-ene-3,17-dione, pH 7.2, 37C
0.081
isoxanthohumol
Homo sapiens
-
pH not specified in the publication, temperature not specified in the publication
0.01 - 0.012
quercetin
0.0203
xanthohumol
Homo sapiens
-
pH not specified in the publication, temperature not specified in the publication
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
57
-
pH 7.2, 37C
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
cell line expresses aromatase mRNA and shows a cytoplasmic pattern of aromatase immunoreactivity. In addition, the cell line expresses estrogen receptor alpha
Manually annotated by BRENDA team
-
cell line expresses aromatase mRNA and shows a cytoplasmic pattern of aromatase immunoreactivity. In addition, the cell line expresses estrogen receptor alpha
Manually annotated by BRENDA team
-
immunoreactivities against aromatase and estradiol-17beta are detected in the cells along the inside of the acinar wall of the testis
Manually annotated by BRENDA team
-
cell line expresses aromatase mRNA and shows a cytoplasmic pattern of aromatase immunoreactivity. In addition, the cell line expresses estrogen receptor alpha
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
-
x * 55000, SDS-PAGE
multimer
-
enzyme is composed of cytochrome P450 and NADPH-cytochrome P450 reductase components
POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
phosphoprotein
-
treatment with alkaline phosphatase results in loss of activity
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
to 1.8 A resolution, in complex with its natural substrate androst-4-ene-3,17-dione. Aromatase has an androgen-specific cleft that binds the androstenedione molecule snugly. Hydrophobic and polar residues complement the steroid backbone
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
from microsome. Full enzymatic activity can be reconstituted with rabbit liver microsomal cytochrome P-450 reductase and Nonidet P-40
-
Show Disease (6032 entries)
Longer loading times are possible.