Information on EC 1.14.14.12 - 3-hydroxy-9,10-secoandrosta-1,3,5(10)-triene-9,17-dione monooxygenase

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The expected taxonomic range for this enzyme is: Mycobacterium tuberculosis

EC NUMBER
COMMENTARY hide
1.14.14.12
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RECOMMENDED NAME
GeneOntology No.
3-hydroxy-9,10-secoandrosta-1,3,5(10)-triene-9,17-dione monooxygenase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
3-hydroxy-9,10-secoandrosta-1,3,5(10)-triene-9,17-dione + FMNH2 + O2 = 3,4-dihydroxy-9,10-secoandrosta-1,3,5(10)-triene-9,17-dione + FMN + H2O
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-hydroxy-9,10-secoandrosta-1,3,5(10)-triene-9,17-dione,FMNH2:oxygen oxidoreductase
This bacterial enzyme participates in the degradation of several steroids, including cholesterol and testosterone. It can use either FADH or FMNH2 as flavin cofactor. The enzyme forms a two-component system with a reductase (HsaB) that utilizes NADH to reduce the flavin, which is then transferred to the oxygenase subunit.
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
P96852: oxygenase subunit hsaA. The reductase subunit hsaB of the two-component enzyme utilizes NADH to reduce the flavin, which is then transferred to the oxygenase subunit
SwissProt
Manually annotated by BRENDA team
P96852: oxygenase subunit hsaA. The reductase subunit hsaB of the two-component enzyme utilizes NADH to reduce the flavin, which is then transferred to the oxygenase subunit
SwissProt
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
3,17-dihydroxy-9,10-seconandrost-1,3,5(10)-triene-9-one + FMNH2 + O2
3,4,17-trihydroxy-9,10-seconandrost-1,3,5(10)-triene-9-one + FMN + H2O
show the reaction diagram
3-hydroxy-9,10-seconandrost-1,3,5(10)-triene-9,17-dione + FADH2 + O2
3,4-dihydroxy-9,10-seconandrost-1,3,5(10)-triene-9,17-dione + FAD + H2O
show the reaction diagram
3-hydroxy-9,10-seconandrost-1,3,5(10)-triene-9,17-dione + FMNH2 + O2
3,4-dihydroxy-9,10-seconandrost-1,3,5(10)-triene-9,17-dione + FMN + H2O
show the reaction diagram
3-hydroxybiphenyl + FMNH2 + O2
2,3-dihydroxybiphenyl + FMN + H2O
show the reaction diagram
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?
additional information
?
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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
3-hydroxy-9,10-seconandrost-1,3,5(10)-triene-9,17-dione + FADH2 + O2
3,4-dihydroxy-9,10-seconandrost-1,3,5(10)-triene-9,17-dione + FAD + H2O
show the reaction diagram
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
FADH2
the enzyme can use FADH or FMNH2 as flavin cofactor
FMNH2
the enzyme can use FADH or FMNH2 as flavin cofactor
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
riboflavin
0.004 mM, 50% inhibition
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.35
3,17-dihydroxy-9,10-seconandrost-1,3,5(10)-triene-9-one
flavin: FMNH2, pH 7.4, 25C
0.097 - 0.2
3-hydroxy-9,10-seconandrost-1,3,5(10)-triene-9,17-dione
1.44
3-hydroxybiphenyl
flavin: FMNH2, pH 7.4, 25C
0.1
O2
flavin: FMNH2, pH 7.4, 25C
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.24
3,17-dihydroxy-9,10-seconandrost-1,3,5(10)-triene-9-one
Mycobacterium tuberculosis
P9WJA1
flavin: FMNH2, pH 7.4, 25C
0.075 - 0.2
3-hydroxy-9,10-seconandrost-1,3,5(10)-triene-9,17-dione
0.11
3-hydroxybiphenyl
Mycobacterium tuberculosis
P9WJA1
flavin: FMNH2, pH 7.4, 25C
0.031
O2
Mycobacterium tuberculosis
P9WJA1
flavin: FMNH2, pH 7.4, 25C
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.7
3,17-dihydroxy-9,10-seconandrost-1,3,5(10)-triene-9-one
Mycobacterium tuberculosis
P9WJA1
flavin: FMNH2, pH 7.4, 25C
41641
0.77 - 1
3-hydroxy-9,10-seconandrost-1,3,5(10)-triene-9,17-dione
12165
0.08
3-hydroxybiphenyl
Mycobacterium tuberculosis
P9WJA1
flavin: FMNH2, pH 7.4, 25C
19271
0.32
O2
Mycobacterium tuberculosis
P9WJA1
flavin: FMNH2, pH 7.4, 25C
9
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
PDB
SCOP
CATH
ORGANISM
UNIPROT
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
hanging drop vapor-diffusion method at 18C, the crystal structure of HsaA to 2.5 A resolution reveales that the enzyme has the same fold, flavin-binding site, and catalytic residues as p-hydroxyphenyl acetate hydroxylase. HsaA prepared aerobically from the Escherichia coli host exists as a mixture of dimers and octamers in solution while HsaA prepared anaerobically from the rhodococcal host exists as a tetramer
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expression in Escherichia coli
Show AA Sequence (302 entries)
Please use the Sequence Search for a specific query.