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Ligand 4,5-9,10-diseco-3-hydroxy-5,9,17-tri-oxoandrosta-1(10),2-diene-4-oic acid

Basic Ligand Information

Molecular Structure

Show all BRENDA pathways known for 4,5-9,10-diseco-3-hydroxy-5,9,17-tri-oxoandrosta-1(10),2-diene-4-oic acid

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (1 result)

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Show Natural Substrate (1 entry)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

3.7.1.17

4,5-9,10-diseco-3-hydroxy-5,9,17-trioxoandrosta-1(10),2-diene-4-oic acid + H2O = ?

717030

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In Vivo Product in Enzyme-catalyzed Reactions (1 result)

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Show Natural Product (1 entry)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.13.11.25

3,4-dihydroxy-9,10-secoandrosta-1,3,5(10)-triene-9,17-dione + O2 = 3-hydroxy-5,9,17-trioxo-4,5:9,10-disecoandrosta-1(10),2-dien-4-oate

0, 396333, 439527, 439528

-

Substrate in Enzyme-catalyzed Reactions (5 results)

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Show Substrate (5 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

3.7.1.17

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

717815

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3.7.1.17

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

654270

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3.7.1.17

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 + ?

718315

-

3.7.1.17

4,5-9,10-diseco-3-hydroxy-5,9,17-trioxoandrosta-1(10),2-diene-4-oic acid + H2O = ?

717030

-

3.7.1.17

4 entries

3.7.1.8

4,5-9,10-diseco-3-hydroxy-5,9,17-trioxoandrosta-1(10),2-diene-4-oic acid + H2O = 3-[(7aR)-7a-hydroxy-1,5-dioxooctahydro-1H-inden-4-yl]propanoic acid + (2Z,4Z)-5-hydroxyhexa-2,4-dienoic acid

717815

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Product in Enzyme-catalyzed Reactions (1 result)

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Show Product (1 entry)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.13.11.25

3,4-dihydroxy-9,10-secoandrosta-1,3,5(10)-triene-9,17-dione + O2 = 3-hydroxy-5,9,17-trioxo-4,5:9,10-disecoandrosta-1(10),2-dien-4-oate

0, 396333, 439527, 439528

-

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (2 results)

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Show Turnover Number (2 entries)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

3.7.1.17

0.000085

-

mutant enzyme S114A, in 100 mM potassium phosphate, pH 7.5, at 25°C

717815

3.7.1.17

0.55

-

wild type enzyme, in 100 mM potassium phosphate, pH 7.5, at 25°C

717815

3.7.1.17

2 entries

K_M Value (1 result)

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Show KM Value (1 entry)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

3.7.1.17

0.017

-

wild type enzyme, in 100 mM potassium phosphate, pH 7.5, at 25°C

717815

References & Links

Literature References (7)

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Show Reference (7 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

396333

-

Nonheme iron dioxygenase

1974

Nozaki, M.

Mol. Mech. Oxygen Activ. (Hayaishi, O., ed.) Academic Press, New York

-

135-165

439527

5506273

3,4-Dihydroxy-9,10-secoandrosta-1,3,5(10)-triene-9,17-dione 4,5-dioxygenase from Nocardia restrictus. I. Isolation of the enzyme and study of its physical and chemical properties

1970

Tai, H.H.; Sih, C.J.

J. Biol. Chem.

245

5062-5071

439528

5908121

Mechanisms of steroid oxidation by microorganisms. IX. On the mechanism of ring A cleavage in the degradation of 9,10-seco steroids by microorganisms

1966

Gibson, D.T.; Wang, K.C.; Sih, C.J.; Whitlock, H.

J. Biol. Chem.

241

551-559

654270

12902225

A new bacterial steroid degradation gene cluster in Comamonas testosteroni TA441 which consists of aromatic-compound degradation genes for seco-steroids and 3-ketosteroid dehydrogenase genes

2003

Horinouchi, M.; Hayashi, T.; Yamamoto, T.; Kudo, T.

Appl. Environ. Microbiol.

69

4421-4430

717030

18097091

Structure of HsaD, a steroid-degrading hydrolase, from Mycobacterium tuberculosis

2007

Lack, N.; Lowe, E.; Liu, J.; Eltis, L.; Noble, M.; Sim, E.; Westwood, I.

Acta Crystallogr. Sect. F

64

2-7

717815

19875455

Characterization of a carbon-carbon hydrolase from Mycobacterium tuberculosis involved in cholesterol metabolism

2010

Lack, N.; Yam, K.; Lowe, E.; Horsman, G.; Owen, R.; Sim, E.; Eltis, L.

J. Biol. Chem.

285

434-443

718315

17264217

A gene cluster encoding cholesterol catabolism in a soil actinomycete provides insight into Mycobacterium tuberculosis survival in macrophages

2007

Van Der Geize, R.; Yam, K.; Heuser, T.; Wilbrink, M.; Hara, H.; Anderton, M.; Sim, E.; Dijkhuizen, L.; Davies, J.; Mohn, W.; Eltis, L.

Proc. Natl. Acad. Sci. USA

104

1947-1952

Links to other databases for 4,5-9,10-diseco-3-hydroxy-5,9,17-tri-oxoandrosta-1(10),2-diene-4-oic acid

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Show Links (1 entry)

ChEBI

PubChem