Ligand 5alpha-androstane-3alpha,17beta-diol

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Basic Ligand Information

Molecular Structure
Picture of 5alpha-androstane-3alpha,17beta-diol (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C19H32O2
5alpha-androstane-3alpha,17beta-diol
CBMYJHIOYJEBSB-KHOSGYARSA-N
Synonyms:
(3R,5S,8R,9S,10S,13S,14S,17S)-10,13-Dimethyl-hexadecahydro-cyclopenta[a]phenanthrene-3,17-diol, 3alpha,17beta-dihydroxy-5alpha-androstane, 3alpha,17beta-dihydroxyandrostane, 3alpha-adiol, 3alpha-androstanediol, 5alpha-androstan-3alpha,17beta-diol, 5alpha-androstan-3alpha-ol-17beta-ol, 5alpha-androstan-3alpha17beta-diol, 5alpha-androstane-3alpha,17beta diol, 5alpha-androstane-3alpha-17beta-diol, 5alpha-androstane 3alpha,17beta-diol, 17-alpha-hydroxysteroid, 17alpha-hydroxysteroid, androstan-3alpha,17beta-diol, androstane-3alpha,17beta-diol, androstane-3alpha,17beta diol
Pathway Source
Pathways

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (5 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
3alpha-androstanediol + NAD+ = 5alpha-dihydrotestosterone + NADH + H+
show the reaction diagram
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5alpha-androstane-3alpha,17beta-diol + NAD+ = androsterone + NADH + H+
show the reaction diagram
-
UDP-D-glucuronate + androstane-3alpha,17beta-diol = UDP + ?
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (15 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
5alpha-dihydrotestosterone + NADPH = 5alpha-androstan-3alpha,17beta-diol + NADP+
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (35 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
5alpha-androstan-3alpha,17beta-diol + NAD+ = 5alpha-androstan-3alpha-ol-17-one + NADH
show the reaction diagram
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5alpha-androstan-3alpha,17beta-diol + NADP+ = ?
show the reaction diagram
-
5alpha-androstane-3alpha,17beta-diol + NADPH = ?
show the reaction diagram
-
5alpha-androstane-3alpha,17beta-diol + NAD+ = ?
show the reaction diagram
-
5alpha-androstane-3alpha,17beta-diol + NAD+ = androsterone + NADH + H+
show the reaction diagram
-
5alpha-androstane-3alpha,17beta-diol + NADP+ = 5alpha-androstane-3alpha-ol-17-one + NADPH
show the reaction diagram
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3'-phosphoadenylylsulfate + 5alpha-androstane-3alpha,17beta-diol = adenosine 3',5'-bisphosphate + ?
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (30 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
5alpha-androstan-3alpha-ol-17-one + NADPH + H+ = 5alpha-androstan-3alpha-ol-17beta-ol + NADP+
show the reaction diagram
-
-
androsterone + NADPH = 5alpha-androstane-3alpha,17beta-diol + NADP+
show the reaction diagram
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androsterone + NAD(P)H = 5alpha-androstane-3alpha,17beta-diol + NAD(P)+ + H+
show the reaction diagram
-
-
5alpha-dihydrotestosterone + NADPH = 5alpha-androstan-3alpha,17beta-diol + NADP+
show the reaction diagram
-
testosterone + NADPH = androstan-3alpha,17beta-diol + androstan-3beta,17beta-diol + 5alpha-dihydrotestosterone
show the reaction diagram
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Inhibitor in Enzyme-catalyzed Reactions (6 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
0.01 mM, 87% inhibition, reaction with 0.002 mM estradiol
-
most potent inhibitor of C19 steroids
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Enzyme Kinetic Parameters

kcat Value (Turnover Number) (14 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
0.27
-
at pH 7.4 and 37°C
3
-
pH 7.4, 37°C recombinant His-tagged enzyme

KM Value (19 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.0042
-
at pH 7.4 and 37°C
0.0192
-
pH 7.4, 37°C recombinant His-tagged enzyme
0.023
-
-

IC50 Value (1 result)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.0046
-
in 0.1 M potassium phosphate, pH 7.4, at 25°C

References & Links

Links to other databases for 5alpha-androstane-3alpha,17beta-diol

ChEBI
PubChem
ChEBI
PubChem