Ligand 17alpha-ethynylestradiol

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Basic Ligand Information

Molecular Structure
Picture of 17alpha-ethynylestradiol (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C20H24O2
17alpha-ethynylestradiol
BFPYWIDHMRZLRN-SLHNCBLASA-N
Synonyms:
17alpha-ethinylestradiol, 17alpha-ethynyl-1,3,5(10)-estratrien-3,17beta-diol, 17alpha-ethynyl-estradiol, 17alpha ethinyl estradiol, 17beta-ethinylestradiol, alpha-ethinylestradiol, ethinyl estradiol, ethinylestradiol, ethynylestradiol

Show all pahtways known for Show all pathways known for 17alpha-ethynylestradiol

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (1 result)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
3'-phosphoadenylyl sulfate + 17alpha-ethinylestradiol = ?
show the reaction diagram
-

Substrate in Enzyme-catalyzed Reactions (13 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
ethynylestradiol + H2O2 = ?
show the reaction diagram
-
3'-phosphoadenylyl sulfate + 17alpha-ethinylestradiol = ?
show the reaction diagram
-
3'-phosphoadenylylsulfate + 17alpha-ethynylestradiol = adenosine 3',5'-bisphosphate + 17alpha-ethynylestradiol 3-sulfate
show the reaction diagram
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Activator in Enzyme-catalyzed Reactions (1 result)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
slightly activates the 3-beta-glucuronidation of estradiol to 116% at 0.005 mM, but inhibits it at 0.1 mM by 23%
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Inhibitor in Enzyme-catalyzed Reactions (11 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
competitive inhibition
-
0.01 mM, 54% inhibition, reaction with 0.002 mM estradiol; inhibits oxidation of testosterone
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reactive intermediates of 17alpha-ethynylestradiol inactivate P450s in a NADPH-dependent mechanism-based manner by a combination of heme alkylation and apoprotein modification
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potent inhibitor, 17alpha-ethinylestradiol binds and inhibits isoform SULT1A1 activity toward 4-nitrophenol and 2-naphthol at low nanomolar concentrations, whereas the compound is not sulfated until significantly higher concentrations are reached
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Enzyme Kinetic Parameters

KM Value (4 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.092
-
-
0.028
-
apparent Km for microsomal preparation
0.191
-
-
0.000007
-
pH 7.4, SULT1E1

Ki Value (6 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.0003
-
-

IC50 Value (5 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.81
-
-

References & Links

Links to other databases for 17alpha-ethynylestradiol

ChEBI
PubChem
ChEBI
PubChem