Ligand progesterone

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Basic Ligand Information

Molecular Structure
Picture of progesterone (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C21H30O2
progesterone
RJKFOVLPORLFTN-LEKSSAKUSA-N
Synonyms:
3,20-pregnene-4, 4-pregnen-3,20-dione, 4-pregnene-3,20-dione, luteol, pregn-4-en-3,20-dione, pregn-4-ene-3,20-dione, progesterone[side 1], progesterone[side 2], progestin, progestins, syngestrone


Show all pahtways known for Show all BRENDA pathways known for progesterone

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (33 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
progesterone + NADPH = 20alpha-hydroxy-4-pregnen-3-one + NADP+
show the reaction diagram
-
progesterone + NAD(P)H + H+ = 20alpha-hydroxyprogesterone + NAD(P)+
show the reaction diagram
-
pregn-4-en-3,20-dione + NADPH + H+ = 3alpha-hydroxypregn-4-en-20-one + NADP+
show the reaction diagram
-
progesterone + NADPH = 20beta-hydroxy-pregn-4-ene-3-one + NADP+
show the reaction diagram
-
progesterone + AH2 + O2 = 9alpha-hydroxyprogesterone + A + H2O
show the reaction diagram
-
Progesterone + NADPH + O2 = Testosterone acetate + NADP+ + H2O
show the reaction diagram
-
progesterone + NADPH = 5alpha-pregnan-3-20-dione + NADP+
show the reaction diagram
-

In Vivo Product in Enzyme-catalyzed Reactions (9 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
20alpha-hydroxyprogesterone + NAD(P)H + H+ = progesterone + NAD(P)+
show the reaction diagram
-
-
3alpha-hydroxypregn-4-en-20-one + NADP+ = pregn-4-en-3,20-dione + NADPH + H+
show the reaction diagram
-
-
pregnenolone + NAD+ = progesterone + NADH + H+
show the reaction diagram
-
-
5alpha-pregnan-3,20-dione + NADP+ = progesterone + NADPH + H+
show the reaction diagram
-
-
5alpha-pregn-3,20-dione + NADP+ = progesterone + NADPH + H+
show the reaction diagram
-
-

Substrate in Enzyme-catalyzed Reactions (81 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
progesterone + NAD(P)H = 3alpha-hydroxy-4-pregnen-20-one + NAD(P)+
show the reaction diagram
-
4-pregnen-3,20-dione + NADPH = ?
show the reaction diagram
-
progesterone + NADPH = 20alpha-hydroxy-4-pregnen-3-one + NADP+
show the reaction diagram
-
progesterone + NAD(P)H = 3alpha-hydroxy-pregn-4-ene-20-one + NAD(P)+
show the reaction diagram
-
progesterone + NADPH + H+ = 20alpha-hydroxyprogesterone + NADP+
show the reaction diagram
-
progesterone + NADPH = pregn-4-ene-20alpha-ol-3-one + NADP+
show the reaction diagram
-
progesterone + NADPH = ? + NADP+
show the reaction diagram
-
progesterone + [reduced NADPH-hemoprotein reductase] + O2 = ?
show the reaction diagram
-
4-pregnene-3,20-dione + 2 reduced ferredoxin [iron-sulfur] cluster + 2 H+ + O2 = 9alpha-hydroxy-4-pregnene-3,20-dione + 2 oxidized ferredoxin [iron-sulfur] cluster + H2O
show the reaction diagram
-
progesterone + reduced adrenodoxin + O2 = 11beta-hydroxyprogesterone + oxidized adrenodoxin + H2O
show the reaction diagram
-
progesterone + AH2 + O2 = 9alpha-hydroxyprogesterone + A + H2O
show the reaction diagram
-

Product in Enzyme-catalyzed Reactions (36 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
20alpha-hydroxy-pregn-4-en-3-one + NADP+ = progesterone + NADPH
show the reaction diagram
-
-
pregnenolone + NADH + H+ = progesterone + NAD+
show the reaction diagram
-
-
20alpha-hydroxyprogesterone + NAD(P)H + H+ = progesterone + NAD(P)+
show the reaction diagram
-
-
3alpha-hydroxypregn-4-en-20-one + NADP+ = pregn-4-en-3,20-dione + NADPH + H+
show the reaction diagram
-
-
20beta-hydroxypregn-4-ene-3-one + NADP+ = pregn-4-ene-3,20-dione + NADPH
show the reaction diagram
-
-
5alpha-pregnan-3,20-dione + NADP+ = progesterone + NADPH + H+
show the reaction diagram
-
-
5alpha-pregn-3,20-dione + NADP+ = progesterone + NADPH + H+
show the reaction diagram
-
-

Activator in Enzyme-catalyzed Reactions (19 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
best inducer
-
physiological levels of progesterone activate PE-NMT and sphingomyelin synthase
-
induces c-Mos expression
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specific induction by 0.01 mM, 7fold increase in sulfation of beta-estradiol, Ishikawa endometrial adenocarcinoma cells
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concentration dependent activation of alkaline phosphatase grown in low phosphate medium
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exposure of HepG2 cells to 0.001 mM progesterone results in a significant increase in the AP-P activity of cell lysates
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up to 2fold activation
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upregulation in breast cancer
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up-regulaion
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up-regulaion
-
ODC activity gradually increases in the presence of progesterone
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1 mM increases the ATPase activity of the enzyme more than 5times
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Inhibitor in Enzyme-catalyzed Reactions (58 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
competitive inhibition vs. indanol
-
inhibition of 3beta-reductase activity
-
competitive to testosterone
-
strong, competitive inhibitor of lactonization of 17-ketosteroids
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progesterone acts as a competitive inhibitor for 11beta-hydroxylase and aldosterone synthase, inhibits aldosterone production by wild-type CYP11B1 and chimeric mutant CYP11B1/B2 in HEK-293 cells. The wild-type is more strongly inhibited than the chimera
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inhibits the synthesis of 5alpha-dihydrotestosterone by competing with 4-en-3-one function of the testosterone for the 5alpha-reductase enzyme
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decreases expression and phosphorylation of GSK-3 beta in the cerebellum but not in the hypothalamus, regulation of tau expression and phosphorylation by progesterone may contribute to the hormonal regulation of cerebellar function by the modification of neuronal cytoskeleton
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competitive inhibitor, inhibits cortisol sulfotransferase activity
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0.5 mM, 29% inhibition
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progesterone decreases adenosine deaminase levels, adenosine deaminase levels show regional specificity with differences among the cerebral hemispheres, cerebellum, and brainstems structures
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weak
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supresses CFTR expression, alleviation of ovarian hyperstimulation syndrome symptoms
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3D Structure of Enzyme-Ligand-Complex (PDB) (4 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (66 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE

KM Value (158 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.0346
-
-
0.031
-
-
0.0076
-
-
0.042
-
-

Ki Value (8 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
TABLE ID
1.5
-
non competitive
1169
0.0018
-
probably minimal physiological importance
339
0.0032
-
competitive substrate with pregnenolone
7485
0.00086
-
-
2747
0.00024
-
-
2500
0.05
-
-
9950

IC50 Value (6 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.015
-
IC50: 0.015 mM
0.0011
-
IC50: 0.0011 mM

References & Links

Links to other databases for progesterone

ChEBI
PubChem
ChEBI
PubChem