Information on EC 1.1.1.145 - 3beta-hydroxy-DELTA5-steroid dehydrogenase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
1.1.1.145
-
RECOMMENDED NAME
GeneOntology No.
3beta-hydroxy-DELTA5-steroid dehydrogenase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
a 3beta-hydroxy-DELTA5-steroid + NAD+ = a 3-oxo-DELTA5-steroid + NADH + H+
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
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redox reaction
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reduction
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
androgen and estrogen metabolism
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androgen biosynthesis
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androstenedione degradation
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cholesterol degradation to androstenedione II (cholesterol dehydrogenase)
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Metabolic pathways
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progesterone biosynthesis
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sitosterol degradation to androstenedione
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Steroid degradation
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Steroid hormone biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
3beta-hydroxy-DELTA5-steroid:NAD+ 3-oxidoreductase
This activity is found in several bifunctional enzymes that catalyse the oxidative conversion of Delta5-3-hydroxy steroids to a Delta4-3-oxo configuration. This conversion is carried out in two separate, sequential reactions; in the first reaction, which requires NAD+, the enzyme catalyses the dehydrogenation of the 3beta-hydroxy steroid to a 3-oxo intermediate. In the second reaction the reduced coenzyme, which remains attached to the enzyme, activates the isomerization of the Delta5 form to a Delta4 form (cf. EC 5.3.3.1, steroid Delta-isomerase). Substrates include dehydroepiandrosterone (which is converted into androst-5-ene-3,17-dione), pregnenolone (converted to progesterone) and cholest-5-en-3-one, an intermediate of cholesterol degradation.
CAS REGISTRY NUMBER
COMMENTARY hide
9044-85-3
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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SwissProt
Manually annotated by BRENDA team
L.
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-
Manually annotated by BRENDA team
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-
Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
TB
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Manually annotated by BRENDA team
i.e. RGV, 9506
SwissProt
Manually annotated by BRENDA team
H.
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Manually annotated by BRENDA team
strain WFU
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Manually annotated by BRENDA team
strain WFU
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
physiological function
-
isoform 3betaHSD2 associates with the inner mitochondrial membrane but does not integrate into the membrane. 3betaHSD2 forms a transient association with the translocases Tim50 and Tom22 and with Tim23. This association occurs primarily through the interaction of Tim50 with the N-terminus of 3betaHSD2 and contributes to enzymatic activity. Tim50 knockdown inhibits catalysis of dehydroepiandrostenedione to androstenedione and pregnenolone to progesterone. Although Tim50 knockdown decreases 3betaHSD2 expression, restoration of expression via proteasome and protease inhibition does not rescue activity
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(S)-1-indanol + NADP+
? + NADPH
show the reaction diagram
-
-
-
-
r
(S)-1-tetralol + NADP+
? + NADPH
show the reaction diagram
-
-
-
-
r
(S)-phenyl-1-butanol + NADP+
? + NADPH
show the reaction diagram
-
-
-
-
r
1,4-naphthoquinone + NADPH
? + NADP+
show the reaction diagram
-
-
-
-
r
1-phenylisatin + NADPH
? + NADP+
show the reaction diagram
-
-
-
-
r
11beta,17alpha,21-trihydroxy-4-pregnen-3,20-dione + NADPH
3beta,11beta,17alpha,21-tetrahydroxy-4-pregnen-20-one + NADP+
show the reaction diagram
-
-
-
-
?
11beta,17alpha,21-trihydroxy-5alpha-pregnane-3,20-dione + NADPH
3beta,11beta,17alpha,21-tetrahydroxy-5alpha-pregnan-20-one + NADP+
show the reaction diagram
-
-
-
-
?
11beta,17alpha,21-trihydroxy-5beta-pregnane-3,20-dione + NADPH
3beta,11beta,17alpha,21-tetrahydroxy-5beta-pregnan-20-one + NADP+
show the reaction diagram
-
-
-
-
?
13,14-dihydro-15-keto-prostaglandin F2 + NADPH
?
show the reaction diagram
-
-
-
-
?
13,14-dihydro-15-keto-prostaglandin F2alpha + NADPH
?
show the reaction diagram
-
-
-
-
?
16alpha-hydroxy-dehydroepiandrosterone + NAD+
?
show the reaction diagram
-
-
-
-
?
16alpha-hydroxy-dehydroepiandrosterone + NAD+
? + NADH
show the reaction diagram
-
-
-
-
?
16beta-hydroxy-dehydroepiandrosterone + NAD+
?
show the reaction diagram
-
-
-
-
?
16beta-hydroxy-dehydroepiandrosterone + NAD+
? + NADH
show the reaction diagram
-
-
-
-
?
17-hydroxyprogesterone + NADPH
3beta,17-dihydroxy-4-pregnen-20-one + NADP+
show the reaction diagram
-
-
-
-
?
17alpha-hydroxypregnenolone + NAD+
17alpha-hydroxy-pregn-5-en-3,20-dione + NADH
show the reaction diagram
-
-
-
?
17beta-hydroxy-5alpha-androstane-3-one + NADPH
3beta,17beta-dihydroxy-5alpha-androstane + NADP+
show the reaction diagram
-
-
-
-
?
17beta-hydroxy-5beta-androstane-3-one + NADPH
3beta,17beta-dihydroxy-5beta-androstane + NADP+
show the reaction diagram
-
-
-
-
?
2,3-heptanedione + NADPH
? + NADP+
show the reaction diagram
-
-
-
-
r
2,3-hexanedione + NADPH
? + NADP+
show the reaction diagram
-
-
-
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r
2,3-pentanedione + NADPH + H+
? + NADP+
show the reaction diagram
-
-
-
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r
3beta,17alpha-dihydroxy-5-pregnen-20-one + NAD(P)+
17alpha-hydroxypregn-5-ene-3,20-dione + NAD(P)H
show the reaction diagram
3beta,7alpha-dihydroxy-5-cholestenoic acid + NAD+
7alpha-hydroxy-3-oxo-5-cholestenoic acid + NADH
show the reaction diagram
-
-
-
-
?
3beta-hydroxy-5-androsten-17-one + NAD+
androstendione + NADH + H+
show the reaction diagram
3beta-hydroxyandrostan-17-one + NAD+
androstan-3,17-dione + NADH
show the reaction diagram
-
-
-
-
?
4,4'-dimethylbenzil + NADPH
? + NADP+
show the reaction diagram
-
-
-
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r
4-androsten-17beta-ol-3-one + NADH + H+
4-androsten-3beta,17beta-diol + NAD+
show the reaction diagram
-
-
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r
4-androsten-3beta,17beta-diol + NAD+
4-androsten-17beta-ol-3-one + NADH
show the reaction diagram
-
-
-
-
?
4-benzoylpyridine + NADPH
? + NADP+
show the reaction diagram
-
-
-
-
r
4-benzylpyridine + NADPH
?
show the reaction diagram
-
-
-
-
?
4-carboxybenzaldehyde + NADP+ + H2O
4-carboxybenzoic acid + NADPH + H+
show the reaction diagram
-
-
-
-
?
4-hexanoylpyridine + NADPH
? + NADP+
show the reaction diagram
-
-
-
-
r
4-nitroacetophenone + NADPH
1-(4-nitrophenyl)ethanol + NADP+
show the reaction diagram
-
-
-
-
?
4-nitrobenzaldehyde + NADPH
4-nitrobenzyl alcohol + NADP+
show the reaction diagram
-
-
-
-
?
4-nitrobenzaldehyde + NADPH
? + NADP+
show the reaction diagram
-
-
-
-
r
5,16-androstadien-3beta-ol + NAD+
5,16-androstadien-3-one + NADH
show the reaction diagram
-
-
-
-
?
5-androsten-3beta-ol-17-one + NAD+
5-androsten-3,17-dione + NADH
show the reaction diagram
-
-
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r
5-pregnen-3beta-ol-2-one + NAD+
progesterone + NADH
show the reaction diagram
5alpha-androstan-3beta-ol-17-one + NADP+
5alpha-androstan-3,17-dione + NADPH
show the reaction diagram
5alpha-androstane-3,17-dione + NADPH
3beta-hydroxy-5alpha-androstane-17-one + NADP+
show the reaction diagram
-
-
-
-
?
5alpha-androstane-3,17-dione + NADPH
5alpha-androstane-3beta-ol-17-one + NADP+
show the reaction diagram
-
-
-
-
r
5alpha-androstane-3beta,17beta-diol + NADP+
5alpha-androstane-17beta-ol-3-one + NADPH
show the reaction diagram
-
-
-
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r
5alpha-androstanediol + NAD+
5alpha-dihydrotestosterone + NADH
show the reaction diagram
-
-
-
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r
5alpha-dihydrotestosterone + NADPH
5alpha-androstane-3beta,17beta-diol + NADP+
show the reaction diagram
-
-
-
-
?
5alpha-dihydrotestosterone + NADPH
? + NADP+
show the reaction diagram
-
-
-
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r
5alpha-pregnan-3beta-ol-20-one + NAD+
5alpha-pregnan-3,20-dione + NADH
show the reaction diagram
-
-
-
-
?
5alpha-pregnane-3,20-dione + NAD(P)H
5alpha-pregnane-3beta-ol-20-one + NAD(P)+
show the reaction diagram
5alpha-pregnane-3,20-dione + NADH
5alpha-pregnane-3beta-ol-20-one + NAD+
show the reaction diagram
-
-
-
r
5alpha-pregnane-3,20-dione + NADPH
5beta-pregnane-3,20-dione + NADPH
show the reaction diagram
-
-
-
-
r
5alpha-pregnane-3beta-ol-20-one + NAD+
5alpha-pregnane-3,20-dione + NADH
show the reaction diagram
-
-
-
r
5alpha-pregnane-3beta-ol-20-one + NADP+
5alpha-pregnane-3,20-dione + NADPH
show the reaction diagram
-
-
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r
5beta-androstan-17beta-ol-3-one + NADPH
5beta-androstane-3beta,17beta-diol + NADP+
show the reaction diagram
-
-
-
-
r
5beta-androstan-3beta-ol-17-one + NADP+
5beta-androstane-3,17-dione + NADPH
show the reaction diagram
-
-
-
-
r
5beta-androstane-3,17-dione + NADPH
3beta-hydroxy-5beta-androstane-17-one + NADP+
show the reaction diagram
-
-
-
-
?
5beta-androstane-3,17-dione + NADPH
5beta-androstan-3beta-ol-17-one + NADP+
show the reaction diagram
-
-
-
-
r
5beta-androstane-3beta,17beta-diol + NADP+
5beta-androstan-17beta-ol-3-one + NADPH
show the reaction diagram
-
-
-
-
r
5beta-pregnan-20alpha-ol-3-one + NADPH + H+
5beta-pregnan-3beta,20alpha-diol + NADP+
show the reaction diagram
-
-
-
-
r
5beta-pregnan-3beta-ol-20-one + NADP+
5beta-pregnan-3,20-dione + NADPH
show the reaction diagram
-
-
-
-
r
5beta-pregnane-3,20-dione + NAD(P)H + H+
5beta-pregnane-3beta-ol-20-one + NAD(P)+
show the reaction diagram
5beta-pregnane-3,20-dione + NADH + H+
5beta-pregnane-3beta-ol-20-one + 5beta-pregnane-3alpha-ol-20-one + NAD+
show the reaction diagram
-
-
-
r
5beta-pregnane-3,20-dione + NADPH + H+
5beta-pregnan-3beta-ol-20-one + NADP+
show the reaction diagram
-
-
-
-
r
5beta-pregnane-3beta,20alpha-diol + NADP+
5beta-pregnane-20alpha-ol-3-one + NADPH + H+
show the reaction diagram
-
-
-
-
r
5beta-pregnane-3beta-ol-20-one + NAD+
5beta-pregnane-3,20-dione + NADH + H+
show the reaction diagram
-
-
-
r
6-tert-butyl-2,3-epoxy-5-cyclohexene-1,4-dione + NADPH
? + NADP+
show the reaction diagram
-
major product has S-configuration
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r
7alpha,25-dihydroxycholesterol + NAD+
7alpha,25-dihydroxy-4-cholesten-3-one + NADH
show the reaction diagram
-
-
-
-
?
7alpha,27-dihydroxycholesterol + NAD+
7alpha,27-dihydroxy-4-cholesten-3-one + NADH
show the reaction diagram
-
-
-
-
?
7alpha-hydroxycholesterol + NAD+
7alpha-hydroxy-4-cholesten-3-one + NADH
show the reaction diagram
-
-
-
-
?
9,10-phenanthrenequinone + NADPH
? + NADP+
show the reaction diagram
9,10-phenantrenequinone + NADPH
?
show the reaction diagram
-
-
-
-
?
all-trans-retinal + NADPH
? + NADP+
show the reaction diagram
-
-
-
-
r
all-trans-retinol + NADP+
? + NADPH
show the reaction diagram
-
-
-
-
r
androst-5-en-3,17-dione + NADH
dehydroepiandrosterone + NAD+
show the reaction diagram
-
-
-
-
r
androst-5-ene-3beta-ol-17-one + NAD+
androst-5-ene-3,17-dione + NADH
show the reaction diagram
androstendiol + NAD+
testosterone + NADH + H+
show the reaction diagram
androstenedione + NADPH + H+
3beta-hydroxy-5-androsten-17-one + NADP+
show the reaction diagram
-
-
-
-
?
androstenone + NADH
beta-androstenol + NAD+
show the reaction diagram
-
-
-
?
benzil + NADPH
(R)-benzoin + NADP+
show the reaction diagram
-
enantiomeric purity of 97% enantiomeric excess
-
-
r
camphorquinone + NADPH + H+
camphorquinol + NADP+
show the reaction diagram
-
-
-
-
?
caprinaldehyde + NADPH
?
show the reaction diagram
-
-
-
-
?
cholesterol + NAD+
cholest-5-en-3-one + NADH
show the reaction diagram
-
-
-
-
?
cyclohexanone + NADPH
cyclohexanol + NADP+
show the reaction diagram
-
-
-
-
?
D-galactose + NADPH
?
show the reaction diagram
-
-
-
-
?
D-glucose + NADPH
?
show the reaction diagram
-
-
-
-
?
D-glucuronic acid + NADPH
?
show the reaction diagram
-
-
-
-
?
D-glyceraldehyde + NADPH
?
show the reaction diagram
-
-
-
-
?
D-xylose + NADPH
?
show the reaction diagram
-
-
-
-
?
dehydroepiandrosterone + NAD+
?
show the reaction diagram
dehydroepiandrosterone + NAD+
androst-5-en-3,17-dione + NADH
show the reaction diagram
dehydroepiandrosterone + NAD+
androst-5-en-3,17-dione + NADH + H+
show the reaction diagram
dehydroepiandrosterone + NADH + H+
androsterone + NAD+
show the reaction diagram
-
-
-
-
?
dehydroepiandrosterone + NADPH
3beta-hydroxy-5-androsten-17-one + NADP+
show the reaction diagram
-
-
-
-
?
dehydrolithocholic acid + NADPH
isolithocholic acid + NADP+
show the reaction diagram
-
-
-
-
r
DELTA5-3beta-hydroxysteroid + NAD+
DELTA4-3-oxosteroid + NADH + H+
show the reaction diagram
diacetyl + NADPH
? + NADP+
show the reaction diagram
-
-
-
-
r
dimethyl-2-oxo-glutarate + NADPH
? + NADP+
show the reaction diagram
-
-
-
-
r
hexanophenone + NADPH
? + NADP+
show the reaction diagram
-
-
-
-
r
hydritantin + NADPH
?
show the reaction diagram
-
-
-
-
?
isatin + NADPH
? + NADP+
show the reaction diagram
-
-
-
-
r
isolithocholic acid + NADP+
dehydrolithocholic acid + NADPH
show the reaction diagram
-
-
-
-
r
menadione + NADPH
? + NADP+
show the reaction diagram
-
-
-
-
r
menadione + NADPH
menadiol + NADP+
show the reaction diagram
-
-
-
-
?
methylglyoxal + NADPH
?
show the reaction diagram
-
-
-
-
?
n-butyrophenone + NADPH
(S)-1-phenyl1-butanol + NADP+
show the reaction diagram
-
major product
-
-
r
phenylglyoxal + NADPH
?
show the reaction diagram
-
-
-
-
?
pregnenolone + NAD(P)+
pregn-5-en-3,20-dione + NAD(P)H
show the reaction diagram
pregnenolone + NAD+
isoprogesterone + NADH + H+
show the reaction diagram
pregnenolone + NAD+
isoprogesterone + progesterone + NADH
show the reaction diagram
-
about 90% odf product is isoprogesterone
-
r
pregnenolone + NAD+
pregn-5-en-3,20-dione + NADH
show the reaction diagram
pregnenolone + NAD+
progesterone + NADH
show the reaction diagram
pregnenolone + NAD+
progesterone + NADH + H+
show the reaction diagram
progesterone + NADPH
3beta-hydroxy-4-pregnen-20-one + NADP+
show the reaction diagram
-
-
-
-
?
prostaglandin E1 + NADPH
?
show the reaction diagram
-
-
-
-
?
prostaglandin E2 + NADPH
?
show the reaction diagram
-
-
-
-
?
pyridine-4-aldehyde + NADPH
? + NADP+
show the reaction diagram
-
-
-
-
r
sitosterol + NAD+
3-oxo-24-ethyl-cholest-5-ene + NADH + H+
show the reaction diagram
testosterone + NADPH
? + NADP+
show the reaction diagram
-
-
-
-
r
testosterone + NADPH + H+
3beta,17beta-dihydroxy-4-androsten + NADP+
show the reaction diagram
-
-
-
-
?
valerophenone + NADPH
? + NADP+
show the reaction diagram
-
-
-
-
r
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
17alpha-hydroxypregnenolone + NAD+
17alpha-hydroxy-pregn-5-en-3,20-dione + NADH
show the reaction diagram
P14060, P26439
-
-
-
?
5-pregnen-3beta-ol-2-one + NAD+
progesterone + NADH
show the reaction diagram
androstenone + NADH
beta-androstenol + NAD+
show the reaction diagram
Q9N119
-
-
-
?
dehydroepiandrosterone + NAD+
?
show the reaction diagram
P14060, P26439
isozyme type 1
-
-
?
dehydroepiandrosterone + NAD+
androst-5-en-3,17-dione + NADH
show the reaction diagram
dehydroepiandrosterone + NADH + H+
androsterone + NAD+
show the reaction diagram
-
-
-
-
?
DELTA5-3beta-hydroxysteroid + NAD+
DELTA4-3-oxosteroid + NADH + H+
show the reaction diagram
pregnenolone + NAD(P)+
pregn-5-en-3,20-dione + NAD(P)H
show the reaction diagram
pregnenolone + NAD+
pregn-5-en-3,20-dione + NADH
show the reaction diagram
pregnenolone + NAD+
progesterone + NADH + H+
show the reaction diagram
additional information
?
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
additional information
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
-
no effect of Ca2+, Sr2+, Ba2+
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(+)-gossypol
(-)-gossypol
(12S,12aS,14bR)-N,N,12a,14b-tetramethyl-3-oxo-1,2,3,4,5,6,7,9,9a,9b,10,11,12,12a,13,14,14a,14b-octadecahydroazepino[3,2,1-de]cyclopenta[i]phenanthridine-12-carboxamide
-
(1R,4S,9aR,11aR)-4,9a,11a-trimethyl-1-((R)-6-methylheptan-2-yl)-3,3a,3b,4,5,8,9,9a,9b,10,11,11a-dodecahydro-1H-cyclopenta[i]phenanthridin-7(2H)-one
-
(1R,9aR,11aR)-9a,11a-dimethyl-1-((R)-6-methylheptan-2-yl)-3,3a,3b,4,5,8,9,9a,9b,10,11,11a-dodecahydro-1H-cyclopenta[i]phenanthridin-7(2H)-one
-
(1S,8bS,10aS)-N,N-diethyl-8b,10a-dimethyl-7-oxo-1,2,3,3a,3b,4,5,7,7a,8,8a,8b,8c,9,10,10a-hexadecahydrocyclopenta[i]cyclopropa[a]phenanthridine-1-carboxamide
-
(1S,8bS,10aS)-N-tert-butyl-8b,10a-dimethyl-7-oxo-1,2,3,3a,3b,4,5,7,7a,8,8a,8b,8c,9,10,10a-hexadecahydrocyclopenta[i]cyclopropa[a]phenanthridine-1-carboxamide
-
(1S,9aR,11aS)-1-(4,5-diphenyl-4,5-dihydro-1,3-oxazol-2-yl)-9a,11a-dimethyl-1,2,3,3a,3b,4,5,8,9,9a,9b,10,11,11a-tetradecahydro-7H-cyclopenta[i]phenanthridin-7-one
-
(1S,9aR,11aS)-5-butyl-N,N,9a,11a-tetramethyl-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxamide
-
(1S,9aR,11aS)-5-hexyl-N,N,9a,11a-tetramethyl-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxamide
-
(1S,9aR,11aS)-6-ethyl-N,N,9a,11a-tetramethyl-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxamide
-
(1S,9aR,11aS)-9a,11a-dimethyl-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxylic acid
-
(1S,9aR,11aS)-9a,11a-dimethyl-N-[4-(morpholin-4-yl)phenyl]-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxamide
-
(1S,9aR,11aS)-N,N,5,9a,11a-pentamethyl-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxamide
-
(1S,9aR,11aS)-N,N,6,9a,11a-pentamethyl-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxamide
-
(1S,9aR,11aS)-N,N,9a,11a-tetramethyl-7-oxo-5-propyl-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxamide
-
(1S,9aR,11aS)-N-(2,5-di-tert-butylphenyl)-9a,11a-dimethyl-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxamide
-
(1S,9aR,11aS)-N-(2-benzoylphenyl)-9a,11a-dimethyl-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxamide
-
(1S,9aR,11aS)-N-tert-butyl-9a,11a-dimethyl-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxamide
-
(1S,9aR,11aS)-N-[2-tert-butyl-5-(trifluoromethyl)phenyl]-9a,11a-dimethyl-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxamide
-
(4aR,6aS,7S)-7-[2,5-bis(trifluoromethyl)benzoyl]-4a,6a-dimethyl-1,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-2H-indeno[5,4-f]quinolin-2-one
-
(4aR,6aS,7S)-N-tert-butyl-4a,6a-dimethyl-2-oxo-2,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-indeno[5,4-f]quinoline-7-carboxamide
-
17alpha-hydroxypregnenolone
-
competitive inhibition
17beta-acetoxy-trilostane
-
-
17beta-estradiol
-
-
20alpha-hydroxy-4-pregnen-3-one
-
-
20beta-hydroxy-4-pregnen-3-one
-
-
3-Chloroacetylpyridine adenine dinucleotide
-
-
4-nonylphenol
-
downregulation of 3beta-hydroxysteroid dehydrogenase mRNA at all doses tested
4alpha,5alpha-epoxy-testosterone
-
-
5'-fluorosulfonylbenzoyl adenosine
-
-
5,10-Secoestr-4-yne-3,10,17-trione
-
irreversible
6-hydroxyflavone
-
0.00056 mM, 50% inhibition; competitive
AgNO3
-
-
androstenedione
-
-
apigenin
Biochanin A
Cetylpyridinium chloride
-
-
corticosterone
-
0.08 mM, 50% inhibition
cyanoketone
-
0.0000076 mM, 50% inhibition; competitive
daidzein
dehydroepiandrosterone
-
0.01 mM reduced conversion of pregnenolone to 50%
deoxycorticosterone
-
-
diethyldicarbonate
-
-
diethylhexyl phthalate
-
downregulation of 3beta-hydroxysteroid dehydrogenase mRNA at all doses tested
diethylstilbestrol
-
downregulation of 3beta-hydroxysteroid dehydrogenase mRNA at all doses tested
Disulfiram
-
-
epostane
estradiol
-
0.0005 mM, 40% inhibition, 0.001 mM, 62% inhibition
estradiol-17beta
-
-
ethynylestradiol
Fe2+
-
1 mM: weak, 100 mM: strong
flavanones
-
diverse derivatives, inhibitory potential determination, overview
flavones
-
diverse derivatives, inhibitory potential determination, overview
formononetin
genistein
Hexestrol
-
-
Hg2+
-
-
isoflavones
-
diverse derivatives, inhibitory potential determination, overview
ketoconazole
-
downregulation of 3beta-hydroxysteroid dehydrogenase mRNA at all doses tested
lauric acid
-
0.05 mM, less than 10% inhibition
Mn2+
-
1 mM: weak
monooctyltin
-
0.081 mM, 50% inhibition; inhibition mechanism, overview
myricetin
-
0.011 mM, 50% inhibition
myristic acid
-
0.05 mM, less than 10% inhibition
N-(Anilino-naphthyl-4)-maleimide
-
-
N-Iodoacetyl-N'-(5-sulfo-1-naphthyl)ethylene diamine
-
-
NADH
-
mixed type inhibition
Norethisterone
Norethisterone acetate
octylphenol
-
downregulation of 3beta-hydroxysteroid dehydrogenase mRNA at all doses tested
oestradiol
-
0.00024 mM, 50% inhibition
p-chloromercuribenzoate
phenylhexane
-
-
pregnenolone
-
competitive inhibition
progesterone
prunetin
-
-
puerarin
-
-
quercetin
Stilbestrol
-
-
testosterone
tributyltin
-
0.012 mM, almost complete loss of activity; complete inhibition at 0.012 mM, the inhibition mechanism is not entirely competitive, overview
trilostane
Zn2+
-
1 mM: strong
additional information
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
flutamide
-
increase in mRNA expression in testis
iodoacetamide
-
-
p-chloromercuribenzoate
-
-
testosterone
-
at low dose, increase in mRNA expression. At doses above 0.2 mg/kg/day, downregulation of 3beta-hydroxysteroid dehydrogenase mRNA
additional information
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.24
(S)-1-indanol
-
pH 7.4, 25C
0.093
(S)-1-tetralol
-
pH 7.4, 25C
0.0084
(S)-phenyl-1-butanol
-
pH 7.4, 25C
0.089
1,4-Naphthoquinone
-
pH 7.4, 25C
0.0052
1-phenylisatin
-
pH 7.4, 25C
0.0038
11beta,17alpha,21-trihydroxy-4-pregnene-3,20-dione
-
-
0.0827
11beta,17alpha,21-trihydroxy-5alpha-pregnane-3,20-dione
-
-
0.0461
11beta,17alpha,21-trihydroxy-5beta-pregnane-3,20-dione
-
-
0.0621
13,14-dihydro-15-keto-prostaglandin F2
-
-
0.13
13,14-dihydro-15-keto-prostaglandin F2alpha
-
-
0.004 - 0.0196
16alpha-hydroxy-dehydroepiandrosterone
0.0014 - 0.0184
16beta-hydroxy-dehydroepiandrosterone
0.206
17-hydroxyprogesterone
-
-
0.0035 - 0.018
17alpha-hydroxypregnenolone
0.684
17beta-hydroxy-5alpha-androstane-3-one
-
-
0.231
17beta-hydroxy-5beta-androstane-3-one
-
-
0.2
2,3-heptanedione
-
pH 7.4, 25C
0.55
2,3-Hexanedione
-
pH 7.4, 25C
10
2,3-Pentanedione
-
pH 7.4, 25C
0.0053
3beta,17alpha-dihydroxy-5-pregen-20-one
-
-
0.0015
4,4'-dimethylbenzil
-
pH 7.4, 25C
1
4-benzoylpyridine
-
pH 7.4, 25C
2.097
4-benzylpyridine
-
-
0.319
4-carboxybenzaldehyde
-
-
0.16
4-hexanoylpyridine
-
pH 7.4, 25C
0.137
4-Nitroacetophenone
-
-
1.966 - 13
4-Nitrobenzaldehyde
0.642
5-androsten-3beta-ol-17-one
-
pH 7.8, 30C
0.0144 - 0.0147
5-androstene-3,17-dione
0.0167 - 0.0179
5alpha-Androstan-3beta-ol-17-one
0.028 - 1.043
5alpha-androstane-3,17-dione
0.016
5alpha-dihydrotestosterone
-
pH 7.4, 25C
0.196 - 0.217
5alpha-pregnane-3,20-dione
0.116 - 0.12
5alpha-pregnane-3beta-ol-20-one
0.0049
5beta-androstan-17beta-ol-3-one
-
pH 7.4, 25C
0.0079
5beta-androstan-3beta-ol-17-one
-
pH 7.4, 25C
0.01 - 0.123
5beta-androstane-3,17-dione
0.0041
5beta-androstane-3beta,17beta-diol
-
pH 7.4, 25C
0.0097
5beta-pregnan-20alpha-ol-3-one
-
pH 7.4, 25C
0.008
5beta-Pregnan-3beta-ol-20-one
-
pH 7.4, 25C
0.0029 - 1.725
5beta-pregnane-3,20-dione
0.008
5beta-pregnane-3beta,20alpha-diol
-
pH 7.4, 25C
0.11 - 0.314
5beta-pregnane-3beta-ol-20-one
0.12
6-tert-butyl-2,3-epoxy-5-cyclohexene-1,4-dione
-
pH 7.4, 25C
0.003
7alpha,27-dihydroxycholesterol
-
-
0.0032
7alpha-hydroxycholesterol
-
-
0.0036 - 2.408
9,10-phenanthrenequinone
0.024
all-trans-retinal
-
pH 7.4, 25C
0.001
allopregnanolone
-
-
0.13
androst-5-ene-3beta-ol-17-one
-
NAD+ as cofactor
0.00016 - 0.00046
androstanediol
0.001
androstenediol
-
-
0.0703
androstenedione
-
-
0.005
benzil
-
pH 7.4, 25C
0.555
Camphorquinone
-
-
0.69
caprinaldehyde
-
-
1.663
cyclohexanone
-
-
0.287
D-galactose
-
-
0.122
D-glucose
-
-
0.465
D-glucuronic acid
-
-
1.07
D-glyceraldehyde
-
-
0.467
D-xylose
-
-
0.00009 - 0.221
dehydroepiandrosterone
0.035
Dehydrolithocholic acid
-
pH 7.4, 25C
54
diacetyl
-
pH 7.4, 25C
1.4
dimethyl-2-oxo-glutarate
-
pH 7.4, 25C
0.036
hexanophenone
-
pH 7.4, 25C
0.466
hydritantin
-
-
0.32
isatin
-
pH 7.4, 25C
0.18 - 0.693
menadione
2.651
methylglyoxal
-
-
0.048
n-butyrophenone
-
pH 7.4, 25C
0.0000047 - 0.27
NAD+
0.0025 - 0.106
NADH
0.0003 - 13
NADP+
2.366
Phenylglyoxal
-
-
0.00004 - 0.09
pregnenolone
0.0346
progesterone
-
-
0.373
prostaglandin E1
-
-
0.0152
prostaglandin E2
-
-
21
Pyridine-4-aldehyde
-
pH 7.4, 25C
0.0055 - 0.0068
stanolone
0.0583
testosterone
-
-
0.054
valerophenone
-
pH 7.4, 25C
additional information
additional information
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.18
(S)-1-indanol
Homo sapiens
-
pH 7.4, 25C
0.25
(S)-1-tetralol
Homo sapiens
-
pH 7.4, 25C
0.075
(S)-phenyl-1-butanol
Homo sapiens
-
pH 7.4, 25C
0.88
1,4-Naphthoquinone
Homo sapiens
-
pH 7.4, 25C
41.7
1-phenylisatin
Homo sapiens
-
pH 7.4, 25C
0.07 - 0.15
16alpha-hydroxy-dehydroepiandrosterone
0.04 - 0.15
16beta-hydroxy-dehydroepiandrosterone
40.2
2,3-heptanedione
Homo sapiens
-
pH 7.4, 25C
16.3
2,3-Hexanedione
Homo sapiens
-
pH 7.4, 25C
26.7
2,3-Pentanedione
Homo sapiens
-
pH 7.4, 25C
3.7
4,4'-dimethylbenzil
Homo sapiens
-
pH 7.4, 25C
2
4-benzoylpyridine
Homo sapiens
-
pH 7.4, 25C
33.3
4-hexanoylpyridine
Homo sapiens
-
pH 7.4, 25C
16.7
4-Nitrobenzaldehyde
Homo sapiens
-
pH 7.4, 25C
0.097
5alpha-androstane-3,17-dione
Homo sapiens
-
pH 7.4, 25C
0.095
5alpha-dihydrotestosterone
Homo sapiens
-
pH 7.4, 25C
0.083
5beta-androstan-17beta-ol-3-one
Homo sapiens
-
pH 7.4, 25C
0.017
5beta-androstan-3beta-ol-17-one
Homo sapiens
-
pH 7.4, 25C
0.077
5beta-androstane-3,17-dione
Homo sapiens
-
pH 7.4, 25C
0.017
5beta-androstane-3beta,17beta-diol
Homo sapiens
-
pH 7.4, 25C
0.07
5beta-pregnan-20alpha-ol-3-one
Homo sapiens
-
pH 7.4, 25C
0.041
5beta-Pregnan-3beta-ol-20-one
Homo sapiens
-
pH 7.4, 25C
0.063
5beta-pregnane-3,20-dione
Homo sapiens
-
pH 7.4, 25C
0.014
5beta-pregnane-3beta,20alpha-diol
Homo sapiens
-
pH 7.4, 25C
2
6-tert-butyl-2,3-epoxy-5-cyclohexene-1,4-dione
Homo sapiens
-
pH 7.4, 25C
11.8
9,10-phenanthrenequinone
Homo sapiens
-
pH 7.4, 25C
0.05
all-trans-retinal
Homo sapiens
-
pH 7.4, 25C
0.0233
allopregnanolone
Bos taurus
-
-
0.0333
androstenediol
Bos taurus
-
-
31.7
benzil
Homo sapiens
-
pH 7.4, 25C
0.02 - 11.6
dehydroepiandrosterone
0.043
Dehydrolithocholic acid
Homo sapiens
-
pH 7.4, 25C
28.3
diacetyl
Homo sapiens
-
pH 7.4, 25C
33.3
dimethyl-2-oxo-glutarate
Homo sapiens
-
pH 7.4, 25C
2.7
hexanophenone
Homo sapiens
-
pH 7.4, 25C
31.7
isatin
Homo sapiens
-
pH 7.4, 25C
0.65
menadione
Homo sapiens
-
pH 7.4, 25C
0.85
n-butyrophenone
Homo sapiens
-
pH 7.4, 25C
0.02 - 0.187
NAD+
0.31 - 1.65
NADH
0.04 - 1.48
pregnenolone
4.7
Pyridine-4-aldehyde
Homo sapiens
-
pH 7.4, 25C
2
valerophenone
Homo sapiens
-
pH 7.4, 25C
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
7.83 - 19.1
16alpha-hydroxy-dehydroepiandrosterone
7.66 - 35.5
16beta-hydroxy-dehydroepiandrosterone
0.0028 - 14.83
dehydroepiandrosterone
0.83 - 4.83
NAD+
106 - 280
NADH
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.00043
17beta-acetoxy-trilostane
-
in 0.02 M potassium phosphate buffer, pH 7.4
0.0028 - 0.00434
4alpha,5alpha-epoxy-testosterone
0.00019
6-hydroxyflavone
-
37C, pH 7.4; recombinant enzyme
0.00000067
cyanoketone
-
37C, pH 7.4; recombinant enzyme
0.000007 - 0.00184
epostane
0.00012
genistein
-
37C, pH 7.4; recombinant enzyme
0.245
NADH
-
pH 8.5, 37C
0.0027
tributyltin
-
37C, pH 8.4; pH 7.5, 37C
0.00001 - 0.197
trilostane
additional information
additional information
-
inhibition kinetics
-
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.00019 - 0.00445
(+)-gossypol
0.00023 - 0.00277
(-)-gossypol
0.043
(12S,12aS,14bR)-N,N,12a,14b-tetramethyl-3-oxo-1,2,3,4,5,6,7,9,9a,9b,10,11,12,12a,13,14,14a,14b-octadecahydroazepino[3,2,1-de]cyclopenta[i]phenanthridine-12-carboxamide
Mycobacterium tuberculosis
P9WQP7
pH 8.5, 30C
0.0008
(1R,4S,9aR,11aR)-4,9a,11a-trimethyl-1-((R)-6-methylheptan-2-yl)-3,3a,3b,4,5,8,9,9a,9b,10,11,11a-dodecahydro-1H-cyclopenta[i]phenanthridin-7(2H)-one
Mycobacterium tuberculosis
P9WQP7
pH 8.5, 30C
0.0005
(1R,9aR,11aR)-9a,11a-dimethyl-1-((R)-6-methylheptan-2-yl)-3,3a,3b,4,5,8,9,9a,9b,10,11,11a-dodecahydro-1H-cyclopenta[i]phenanthridin-7(2H)-one
Mycobacterium tuberculosis
P9WQP7
pH 8.5, 30C
0.54
(1S,8bS,10aS)-N,N-diethyl-8b,10a-dimethyl-7-oxo-1,2,3,3a,3b,4,5,7,7a,8,8a,8b,8c,9,10,10a-hexadecahydrocyclopenta[i]cyclopropa[a]phenanthridine-1-carboxamide
Mycobacterium tuberculosis
P9WQP7
pH 8.5, 30C
0.2
(1S,8bS,10aS)-N-tert-butyl-8b,10a-dimethyl-7-oxo-1,2,3,3a,3b,4,5,7,7a,8,8a,8b,8c,9,10,10a-hexadecahydrocyclopenta[i]cyclopropa[a]phenanthridine-1-carboxamide
Mycobacterium tuberculosis
P9WQP7
value above, pH 8.5, 30C
0.009
(1S,9aR,11aS)-1-(4,5-diphenyl-4,5-dihydro-1,3-oxazol-2-yl)-9a,11a-dimethyl-1,2,3,3a,3b,4,5,8,9,9a,9b,10,11,11a-tetradecahydro-7H-cyclopenta[i]phenanthridin-7-one
Mycobacterium tuberculosis
P9WQP7
pH 8.5, 30C
0.05
(1S,9aR,11aS)-5-butyl-N,N,9a,11a-tetramethyl-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxamide
Mycobacterium tuberculosis
P9WQP7
value above, pH 8.5, 30C
0.156
(1S,9aR,11aS)-5-hexyl-N,N,9a,11a-tetramethyl-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxamide
Mycobacterium tuberculosis
P9WQP7
pH 8.5, 30C
0.26
(1S,9aR,11aS)-6-ethyl-N,N,9a,11a-tetramethyl-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxamide
Mycobacterium tuberculosis
P9WQP7
value above, pH 8.5, 30C
0.2
(1S,9aR,11aS)-9a,11a-dimethyl-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxylic acid
Mycobacterium tuberculosis
P9WQP7
value above, pH 8.5, 30C
0.1
(1S,9aR,11aS)-9a,11a-dimethyl-N-[4-(morpholin-4-yl)phenyl]-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxamide
Mycobacterium tuberculosis
P9WQP7
value above, pH 8.5, 30C
0.4
(1S,9aR,11aS)-N,N,5,9a,11a-pentamethyl-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxamide
0.05
(1S,9aR,11aS)-N,N,9a,11a-tetramethyl-7-oxo-5-propyl-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxamide
Mycobacterium tuberculosis
P9WQP7
value above, pH 8.5, 30C
0.023
(1S,9aR,11aS)-N-(2,5-di-tert-butylphenyl)-9a,11a-dimethyl-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxamide
Mycobacterium tuberculosis
P9WQP7
pH 8.5, 30C
0.027
(1S,9aR,11aS)-N-(2-benzoylphenyl)-9a,11a-dimethyl-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxamide
Mycobacterium tuberculosis
P9WQP7
pH 8.5, 30C
0.14
(1S,9aR,11aS)-N-tert-butyl-9a,11a-dimethyl-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxamide
Mycobacterium tuberculosis
P9WQP7
pH 8.5, 30C
0.027
(1S,9aR,11aS)-N-[2-tert-butyl-5-(trifluoromethyl)phenyl]-9a,11a-dimethyl-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxamide
Mycobacterium tuberculosis
P9WQP7
pH 8.5, 30C
0.15
(4aR,6aS,7S)-7-[2,5-bis(trifluoromethyl)benzoyl]-4a,6a-dimethyl-1,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-2H-indeno[5,4-f]quinolin-2-one
Mycobacterium tuberculosis
P9WQP7
value above, pH 8.5, 30C
0.312
(4aR,6aS,7S)-N-tert-butyl-4a,6a-dimethyl-2-oxo-2,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-indeno[5,4-f]quinoline-7-carboxamide
Mycobacterium tuberculosis
P9WQP7
pH 8.5, 30C
0.0066
Cetylpyridinium chloride
Homo sapiens
-
pH 7.4, 25C
0.0002
epostane
Homo sapiens
-
in 0.02 M potassium phosphate buffer, pH 7.4
0.0059
genistein
Homo sapiens
-
pH 7.4, 25C
0.023
phenylhexane
Homo sapiens
-
pH 7.4, 25C
0.0027
quercetin
Homo sapiens
-
pH 7.4, 25C
0.0049
trilostane
Homo sapiens
-
in 0.02 M potassium phosphate buffer, pH 7.4
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.0033
-
7alpha,25-dihydroxycholesterol as substrate
0.0041
-
-
0.0043
-
mitochondria
0.0062
-
wild type, microsomes
0.0091
-
placental microsomes, 3beta-HSD activity
0.0099
-
wild type, mitochondria
0.0145
-
Sf9-cells, 3beta-HSD activity
0.0158
-
microsomes
0.0172
-
placental microsomes, isomerase activity
0.0225
-
283-310 deletion, cytosol
0.0257
-
Sf9-cells, isomerase activity
0.0524
-
-
0.155
-
-
0.175
-
3beta,7alpha-dihydroxy-5-cholestenoic acid as substrate
0.19
-
purification step D
0.677
-
-
0.838
-
7alpha,27-dihydroxycholesterol as substrate
1.489
-
7alpha-hydroxycholesterol as substrate
2.88
-
-
88.9
-
; purified enzyme
additional information