Information on EC 6.2.1.41 - 3-[(3aS,4S,7aS)-7a-methyl-1,5-dioxo-octahydro-1H-inden-4-yl]propanoate-CoA ligase

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The expected taxonomic range for this enzyme is: Mycobacterium tuberculosis

EC NUMBER
COMMENTARY hide
6.2.1.41
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RECOMMENDED NAME
GeneOntology No.
3-[(3aS,4S,7aS)-7a-methyl-1,5-dioxo-octahydro-1H-inden-4-yl]propanoate-CoA ligase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
ATP + 3-[(3aS,4S,7aS)-7a-methyl-1,5-dioxo-octahydro-1H-inden-4-yl]propanoate + CoA = AMP + diphosphate + 3-[(3aS,4S,7aS)-7a-methyl-1,5-dioxo-octahydro-1H-inden-4-yl]propanoyl-CoA
show the reaction diagram
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
androstenedione degradation
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Metabolic pathways
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Microbial metabolism in diverse environments
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Steroid degradation
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androgen and estrogen metabolism
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SYSTEMATIC NAME
IUBMB Comments
3-[(3aS,4S,7aS)-7a-methyl-1,5-dioxo-octahydro-1H-inden-4-yl]propanoate:CoA ligase (AMP-forming)
The enzyme, characterized from actinobacterium Mycobacterium tuberculosis, catalyses a step in the degradation of cholesterol and cholate. The enzyme is very specific for its substrate, and requires that the side chain at C17 is completely removed.
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
ATP + 3-[(3aS,4S,7aS)-7a-methyl-1,5-dioxo-octahydro-1H-inden-4-yl]propanoate + CoA
AMP + diphosphate + 3-[(3aS,4S,7aS)-7a-methyl-1,5-dioxo-octahydro-1H-inden-4-yl]propanoyl-CoA
show the reaction diagram
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?
ATP + 3aalpha-H-4a(3'-propanoate)-5alpha-hydroxy-7alphabeta-methylhexahydro-1-indanone
?
show the reaction diagram
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?
additional information
?
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no activity with 3aalpha-H-4a(3'-propanoate)-5alpha-hydroxy-7alphabeta-methylhexahydro-1-indanone-D-lactone, 3-oxo-23,24-bisnorchol-4-en-22-oate, cholate, and 3beta-hydroxy-5-cholesten-26-oate
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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
ATP + 3-[(3aS,4S,7aS)-7a-methyl-1,5-dioxo-octahydro-1H-inden-4-yl]propanoate + CoA
AMP + diphosphate + 3-[(3aS,4S,7aS)-7a-methyl-1,5-dioxo-octahydro-1H-inden-4-yl]propanoyl-CoA
show the reaction diagram
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?
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
additional information
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neither 1beta(2'-propanoate)-3aalpha-H-4a(3''-propanoate)-7alphabeta-methylhexahydro-5-indanone nor 3aalpha-H-4aalpha(3'-propanoic acid)-5alpha-hydroxy-7alphabeta-methylhexahydro-1-indanone-D-lactone significantly inhibit enzyme activity
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0098
3-[(3aS,4S,7aS)-7a-methyl-1,5-dioxo-octahydro-1H-inden-4-yl]propanoate
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at pH 7.3 and 22C
3
3aalpha-H-4a(3'-propanoate)-5alpha-hydroxy-7alphabeta-methylhexahydro-1-indanone
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at pH 7.3 and 22C
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0.11
CoA
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at pH 7.3 and 22C
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
7.1
3-[(3aS,4S,7aS)-7a-methyl-1,5-dioxo-octahydro-1H-inden-4-yl]propanoate
Mycobacterium tuberculosis
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at pH 7.3 and 22C
13
3aalpha-H-4a(3'-propanoate)-5alpha-hydroxy-7alphabeta-methylhexahydro-1-indanone
Mycobacterium tuberculosis
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at pH 7.3 and 22C
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7.5
CoA
Mycobacterium tuberculosis
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at pH 7.3 and 22C
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
730
3-[(3aS,4S,7aS)-7a-methyl-1,5-dioxo-octahydro-1H-inden-4-yl]propanoate
Mycobacterium tuberculosis
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at pH 7.3 and 22C
167616
4.4
3aalpha-H-4a(3'-propanoate)-5alpha-hydroxy-7alphabeta-methylhexahydro-1-indanone
Mycobacterium tuberculosis
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at pH 7.3 and 22C
197795
66
CoA
Mycobacterium tuberculosis
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at pH 7.3 and 22C
18
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
Ni-Sepharose 6 column chromatography
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli Rosetta(DE3)pLysS cells
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