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Ligand (22R)-22-hydroxycholesterol

Basic Ligand Information

Molecular Structure

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (2 results)

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Show Natural Substrate (2 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.14.15.6

(22R)-22-hydroxycholesterol + 2 reduced adrenodoxin + O2 = (20R,22R)-20,22-dihydroxycholesterol + 2 oxidized adrenodoxin + H2O

725962, 725459

3mzs, 3D-view

1.14.15.6

(22R)-22-hydroxycholesterol + 2 reduced adrenodoxin + O2 = (20R,22R)-20,22-dihydroxycholesterol + 2 oxidized adrenodoxin + H2O

725962, 725459

3n9z, 3D-view

1.14.15.6

2 entries

In Vivo Product in Enzyme-catalyzed Reactions (2 results)

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Show Natural Product (2 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.14.15.6

cholesterol + 2 reduced adrenodoxin + O2 = (22R)-22-hydroxycholesterol + 2 oxidized adrenodoxin + H2O

0

3mzs, 3D-view

1.14.15.6

cholesterol + 2 reduced adrenodoxin + O2 = (22R)-22-hydroxycholesterol + 2 oxidized adrenodoxin + H2O

0

3n9z, 3D-view

1.14.15.6

2 entries

Substrate in Enzyme-catalyzed Reactions (6 results)

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Show Substrate (6 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.14.15.6

(22R)-22-hydroxycholesterol + 2 reduced adrenodoxin + O2 = (20R,22R)-20,22-dihydroxycholesterol + 2 oxidized adrenodoxin + H2O

725962, 744345, 725459

3mzs, 3D-view

1.14.15.6

(22R)-22-hydroxycholesterol + 2 reduced adrenodoxin + O2 = (20R,22R)-20,22-dihydroxycholesterol + 2 oxidized adrenodoxin + H2O

725962, 744345, 725459

3n9z, 3D-view

1.14.15.6

22(R)-hydroxycholesterol + reduced adrenodoxin + O2 = ? + oxidized adrenodoxin + H2O

657647, 702403

3mzs, 3D-view

1.14.15.6

22(R)-hydroxycholesterol + reduced adrenodoxin + O2 = ? + oxidized adrenodoxin + H2O

657647, 702403

3n9z, 3D-view

1.14.15.6

22(R)-hydroxycholesterol + reduced adrenodoxin + O2 = pregnenolone + oxidized adrenodoxin + H2O

658508

3mzs, 3D-view

1.14.15.6

22(R)-hydroxycholesterol + reduced adrenodoxin + O2 = pregnenolone + oxidized adrenodoxin + H2O

658508

3n9z, 3D-view

1.14.15.6

6 entries

Product in Enzyme-catalyzed Reactions (2 results)

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Show Product (2 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.14.15.6

cholesterol + 2 reduced adrenodoxin + O2 = (22R)-22-hydroxycholesterol + 2 oxidized adrenodoxin + H2O

0

3mzs, 3D-view

1.14.15.6

cholesterol + 2 reduced adrenodoxin + O2 = (22R)-22-hydroxycholesterol + 2 oxidized adrenodoxin + H2O

0

3n9z, 3D-view

1.14.15.6

2 entries

Inhibitor in Enzyme-catalyzed Reactions (1 result)

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Show Inhibitors (1 entry)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

3.1.1.1

slight inhibition of CES1, not CES2

707570

-

3D Structure of Enzyme-Ligand-Complex (PDB) (6 results)

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Show 3D Structure of Enzyme-Ligand-Complex (PDB) (6 entries)

EC NUMBER

ENZYME 3D STRUCTURE

1.14.15.6

3mzs, 3D-view

1.14.15.6

3n9z, 3D-view

1.14.15.6

3mzs, 3D-view

1.14.15.6

3n9z, 3D-view

1.14.15.6

3mzs, 3D-view

1.14.15.6

3n9z, 3D-view

1.14.15.6

6 entries

Enzyme Kinetic Parameters

References & Links

Literature References (7)

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Show Reference (7 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

657647

12392719

The effect of glycerol on cytochrome P450scc (CYP11A1) spin state, activity, and hydration

2002

Headlam, M.J.; Tuckey, R.C.

Arch. Biochem. Biophys.

407

95-102

658508

12823901

Formation and functioning of fused cholesterol side-chain cleavage enzymes

2003

Nazarov, P.A.; Drutsa, V.L.; Miller, W.L.; Shkumatov, V.M.; Luzikov, V.N.; Novikova, L.A.

DNA Cell Biol.

22

243-252

702403

18621100

Import of hybrid forms of CYP11A1 into yeast mitochondria

2008

Minenko, A.N.; Novikova, L.A.; Luzikov, V.N.; Kovaleva, I.E.

Biochim. Biophys. Acta

1780

1121-1130

707570

19761868

Inhibition of carboxylesterase activity of THP1 monocytes/macrophages and recombinant human carboxylesterase 1 by oxysterols and fatty acids

2010

Crow, J.A.; Herring, K.L.; Xie, S.; Borazjani, A.; Potter, P.M.; Ross, M.K.

Biochim. Biophys. Acta

1801

31-41

725459

21159775

Structural basis for three-step sequential catalysis by the cholesterol side chain cleavage enzyme CYP11A1

2011

Mast, N.; Annalora, A.; Lodowski, D.; Palczewski, K.; Stout, C.; Pikuleva, I.

J. Biol. Chem.

286

5607-5613

725962

21075169

Localization and functional activity of cytochrome P450 side chain cleavage enzyme (CYP11A1) in the adult rat kidney

2011

Pagotto, M.; Roldan, M.; Pagotto, R.; Lugano, M.; Pisani, G.; Rogic, G.; Molinas, S.; Trumper, L.; Pignataro, O.; Monasterolo, L.

Mol. Cell. Endocrinol.

332

253-260

744345

26603348

Evidence that compound I is the active species in both the hydroxylase and lyase steps by which P450scc converts cholesterol to pregnenolone EPR/ENDOR/cryoreduction/annealing Studies

2015

Davydov, R.; Strushkevich, N.; Smil, D.; Yantsevich, A.; Gilep, A.; Usanov, S.; Hoffman, B.M.

Biochemistry

54

7089-7097

Links to other databases for (22R)-22-hydroxycholesterol

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Show Links (1 entry)

ChEBI

PubChem