Information on EC 3.7.1.17 - 4,5:9,10-diseco-3-hydroxy-5,9,17-trioxoandrosta-1(10),2-diene-4-oate hydrolase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
3.7.1.17
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RECOMMENDED NAME
GeneOntology No.
4,5:9,10-diseco-3-hydroxy-5,9,17-trioxoandrosta-1(10),2-diene-4-oate hydrolase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
(1E,2Z)-3-hydroxy-5,9,17-trioxo-4,5:9,10-disecoandrosta-1(10),2-dien-4-oate + H2O = 3-[(3aS,4S,7aS)-7a-methyl-1,5-dioxo-octahydro-1H-inden-4-yl]propanoate + (2Z,4Z)-2-hydroxyhexa-2,4-dienoate
show the reaction diagram
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
androstenedione degradation
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Steroid degradation
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androgen and estrogen metabolism
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SYSTEMATIC NAME
IUBMB Comments
4,5:9,10-diseco-3-hydroxy-5,9,17-trioxoandrosta-1(10),2-diene-4-oate hydrolase ( (2Z,4Z)-2-hydroxyhexa-2,4-dienoate-forming)
The enzyme is involved in the bacterial degradation of the steroid ring structure, and is involved in degradation of multiple steroids, such as testosterone [1], cholesterol [2], and sitosterol.
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoate + H2O
?
show the reaction diagram
2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid + H2O
?
show the reaction diagram
4,5-9,10-diseco-3-hydroxy-5,9,17-tri-oxoandrosta-1(10),2-diene-4-oic acid + H2O
9,17-dioxo-1,2,3,4,10,19-hexanorandrostan-5-oic acid + 2-hydroxy-hexa-2,4-dienoic acid
show the reaction diagram
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best substrate
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-
?
4,5-9,10-diseco-3-hydroxy-5,9,17-trioxoandrosta-1(10),2-dien-4-oic acid + H2O
9,17-dioxo-1,2,3,4,10,19-hexanorandrostan-5-oic acid + 2-hydroxyhexa-2,4-dienoic acid
show the reaction diagram
4,5-9,10-diseco-3-hydroxy-5,9,17-trioxoandrosta-1(10),2-diene-4-oic acid + H2O
9,17-dioxo-1,2,3,4,10,19-hexanorandrostan-5-oic acid + ?
show the reaction diagram
4,5-9,10-diseco-3-hydroxy-5,9,17-trioxoandrosta-1(10),2-diene-4-oic acid + H2O
?
show the reaction diagram
8-(2-chlorophenyl)-2-hydroxy-5-methyl-6-oxoocta-2,4-dienoic acid + H2O
?
show the reaction diagram
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?
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
4,5-9,10-diseco-3-hydroxy-5,9,17-trioxoandrosta-1(10),2-diene-4-oic acid + H2O
?
show the reaction diagram
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
3,4-dichloroisocoumarin
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a broad spectrum covalent inhibitor of serine proteases, the structural homologues of 3,4-dichloroisocoumarin, 7-amino-4-chloro-3-methoxy-1H-2-benzopyran and 3-phenyl-1H-2-benzopyran-1-one, show significantly poorer inhibition
3-phenyl-1H-2-benzopyran-1-one
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weak inhibition
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4-(2-aminoethyl)benzenesulfonyl fluoride
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weak inhibition
4-amidinophenylmethanesulfonyl fluoride
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weak inhibition
4-nitrophenyl-4-[bis(1,3-benzodioxol-5-yl)(hydroxy)methyl]piperidine-1-carboxylate
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covalent inhibitor
7-amino-4-chloro-3-methoxy-1H-2-benzopyran
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weak inhibition
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benzamidine
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weak inhibition
eserine
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an acetylcholinesterase inhibitor
leupeptin
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weak inhibition
nafamostat mesylate
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weak inhibition
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Neostigmine
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an acetylcholinesterase inhibitor
Trichlorfon
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an acetylcholinesterase inhibitor, weak inhibition
additional information
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inhibition of HsaD by serine protease inhibitors. No inhibition by acetylcholinesterase inhibitors edrophonium, tacrine, and pyridostigmine. Consistent with the lack of a cysteine residue in the active site of HsaD, covalent inhibitor nicotinamide does not significantly inhibit HsaD
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.019
2-hydroxy-6-oxo-6-phenyl-2,4-hexadienoic acid
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in 20 mM HEPES, 80 mM NaCl, at pH 8.0 and 25°C
0.008 - 0.23
2-Hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid
0.017
4,5-9,10-diseco-3-hydroxy-5,9,17-tri-oxoandrosta-1(10),2-diene-4-oic acid
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wild type enzyme, in 100 mM potassium phosphate, pH 7.5, at 25°C
0.31
8-(2-chlorophenyl)-2-hydroxy-5-methyl-6-oxoocta-2,4-dienoic acid
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wild type enzyme, in 100 mM potassium phosphate, pH 7.5, at 25°C
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.066 - 0.25
2-Hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid
0.000085 - 0.55
4,5-9,10-diseco-3-hydroxy-5,9,17-tri-oxoandrosta-1(10),2-diene-4-oic acid
0.33
8-(2-chlorophenyl)-2-hydroxy-5-methyl-6-oxoocta-2,4-dienoic acid
Mycobacterium tuberculosis
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wild type enzyme, in 100 mM potassium phosphate, pH 7.5, at 25°C
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1.129 - 9
2-Hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid
3589
33
4,5-9,10-diseco-3-hydroxy-5,9,17-tri-oxoandrosta-1(10),2-diene-4-oic acid
Mycobacterium tuberculosis
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wild type enzyme, in 100 mM potassium phosphate, pH 7.5, at 25°C
28608
1.06
8-(2-chlorophenyl)-2-hydroxy-5-methyl-6-oxoocta-2,4-dienoic acid
Mycobacterium tuberculosis
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wild type enzyme, in 100 mM potassium phosphate, pH 7.5, at 25°C
15228
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.63
PMSF
Mycobacterium tuberculosis
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pH 7.5, 21°C, recombinant enzyme
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
PDB
SCOP
CATH
ORGANISM
UNIPROT
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain CDC 1551 / Oshkosh)
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
33800
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x * 33800, His6-tagged enzyme, estimated from SDS-PAGE
132000
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calculated from amino acid sequence
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
homotetramer
tetramer
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
mutant enzyme S114A, sitting drop vapor diffusion method, using 200 mM KSCN, 24% polyethylene glycol 3.35 K, and 100 mM bis-tris propane, pH 7.0
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sitting drop vapor diffusion method, using 30% (w/v) PEG 3000, 0.1?M CHES, pH 9.5
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TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
60 - 70
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the enzyme retains more than 95% of its activity after incubation at 60°C for 30 min. Hydrolytic activity is significantly decreased after incubation at 70°C
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
Ni affinity column chromatography
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Ni-NTA column chromatography, gel filtration
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recombinant enzyme from Pseudomonas putida strain KT2442
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Source 15Q anion exchange resin column chromatography
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli strain GJ1158
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expressed in Pseudomonas putida strain KT2442
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expressed in Pseudomonas putida strain KT4224
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recombinant expression in Pseudomonas putida strain KT2442
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
S114A
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the mutant has a 6500fold lower kcat for 4,5–9,10-diseco-3-hydroxy-5,9,17-tri-oxoandrosta-1(10),2-diene-4-oic acid compared to the wild type enzyme
Show AA Sequence (107 entries)
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