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1.14.15.6: cholesterol monooxygenase (side-chain-cleaving)

This is an abbreviated version!
For detailed information about cholesterol monooxygenase (side-chain-cleaving), go to the full flat file.

Word Map on EC 1.14.15.6

Reaction

(20R,22R)-20,22-dihydroxy-cholesterol
+ 2 reduced adrenodoxin +
O2
+ 2 H+ =
pregnenolone
+
4-Methylpentanal
+ 2 oxidized adrenodoxin + 2 H2O

Synonyms

C27-side chain cleavage enzyme, cholesterol 20-22-desmolase, cholesterol C20-22 desmolase, cholesterol C20-C22 lyase, cholesterol desmolase, cholesterol hydroxylase, cholesterol side chain cleavage cytochrome P450, cholesterol side chain cleavage enzyme, cholesterol side-chain cleavage cytochrome P450, cholesterol side-chain cleavage cytochrome P450 enzyme, cholesterol side-chain cleavage enzyme, cholesterol side-chain-cleaving enzyme, cholesterol side-cleaving enzyme, CYP 11A1, Cyp11a, CYP11A1, CYPXIA1, cytochrome P-450scc, cytochrome P450 11A1, cytochrome P450 cholesterol side chain cleavage, cytochrome P450 cholesterol side-chain cleavage, cytochrome P450 side chain cleavage enzyme, cytochrome P450-mediated cholesterol side-chain cleavage enzyme, cytochrome P450-mediated side-chain cleavage enzyme, cytochrome P450scc, desmolase, steroid 20-22, endoenzymes, cholesterol side-chain-cleaving, enzymes, cholesterol side-chain-cleaving, P450 11A1, P450 cholesterol side chain cleaving enzyme, P450 cholesterol side-chain cleavage enzyme, P450(scc), P450scc, steroid 20-22 desmolase, steroid 20-22-lyase

ECTree

     1 Oxidoreductases
         1.14 Acting on paired donors, with incorporation or reduction of molecular oxygen
             1.14.15 With reduced iron-sulfur protein as one donor, and incorporation of one atom of oxygen into the other donor
                1.14.15.6 cholesterol monooxygenase (side-chain-cleaving)

Substrates Products

Substrates Products on EC 1.14.15.6 - cholesterol monooxygenase (side-chain-cleaving)

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SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(20R,22R)-20,22-dihydroxy-cholesterol + 2 reduced adrenodoxin + O2
pregnenolone + 4-methylpentanal + 2 oxidized adrenodoxin + 2 H2O
show the reaction diagram
(20S)-22-thiacholesterol + reduced adrenodoxin + O2
(20S,22R)-22-thiacholesterol S-oxide + (20S,22S)-22-thiacholesterol S-oxide
show the reaction diagram
-
-
(22R)-sulfoxide preferentially formed by a factor of 4.2 to 1 over (22S)-sulfoxide
?
(22R)-22-hydroxycholesterol + 2 reduced adrenodoxin + O2
(20R,22R)-20,22-dihydroxycholesterol + 2 oxidized adrenodoxin + H2O
show the reaction diagram
17,20-dihydroxyvitamin D2 + reduced adrenodoxin + O2
17,20,24-trihydroxyvitamin D2 + oxidized adrenodoxin + O2
show the reaction diagram
-
is slowly metabolized
-
-
?
20,23-dihydroxyvitamin D3 + reduced adrenodoxin + O2
17,20,23-trihydroxyvitamin D3 + oxidized adrenodoxin + H2O
show the reaction diagram
-
-
-
-
?
20,23-dihydroxyvitamin D3 + reduced adrenodoxin + O2
17alpha,20,23-trihydroxyvitamin D3 + oxidized adrenodoxin + H2O
show the reaction diagram
-
-
-
-
?
20-hydroxyvitamin D2 + reduced adrenodoxin + O2
17,20,24-trihydroxyvitamin D2 + oxidized adrenodoxin + O2
show the reaction diagram
-
is a better substrate than vitamin D2 itself
-
-
?
20-hydroxyvitamin D3 + reduced adrenodoxin + O2
20,23-dihydroxyvitamin D3 + 17alpha,20,23-trihydroxyvitamin D3 + oxidized adrenodoxin + H2O
show the reaction diagram
-
-
-
-
?
20-hydroxyvitamin D3 + reduced adrenodoxin + O2
20,23-dihydroxyvitamin D3 + oxidized adrenodoxin + H2O
show the reaction diagram
-
-
-
-
?
20alpha, 22(R)-dihydroxycholesterol + reduced adrenodoxin + O2
? + oxidized adrenodoxin + H2O
show the reaction diagram
-
-
-
-
?
20alpha-hydroxycholesterol + reduced adrenodoxin + O2
pregnenolone + 4-methylpentanal + oxidized adrenodoxin + H2O
show the reaction diagram
22(R)-hydroxycholesterol + reduced adrenodoxin + O2
? + oxidized adrenodoxin + H2O
show the reaction diagram
22(R)-hydroxycholesterol + reduced adrenodoxin + O2
pregnenolone + oxidized adrenodoxin + H2O
show the reaction diagram
25-hydroxycholesterol + O2 + reduced ferredoxin
pregnenolone + H2O + ferredoxin + 4-hydroxy-4-methylpentanal
show the reaction diagram
-
-
-
?
25-hydroxycholesterol + reduced adrenodoxin + O2
pregnenolone + oxidized adrenodoxin + H2O
show the reaction diagram
-
-
-
?
cholesterol + 2 reduced adrenodoxin + O2
(22R)-22-hydroxycholesterol + 2 oxidized adrenodoxin + H2O
show the reaction diagram
cholesterol + 6 reduced adrenodoxin + 3 O2
pregnenolone + 4-methylpentanal + 6 oxidized adrenodoxin + 4 H2O
show the reaction diagram
cholesterol + 6 reduced adrenodoxin mutant S112W + 3 O2
pregnenolone + 4-methylpentanal + 6 oxidized adrenodoxin mutant S112W + 4 H2O
show the reaction diagram
-
overall reaction, adrenodoxin mutant S112W gives a 14fold higher catalytic efficiency compared to wild-type adrenodoxin
-
-
?
cholesterol + reduced adrenal ferredoxin + O2
pregnenolone + 4-methylpentanal + oxidized adrenal ferredoxin
show the reaction diagram
cholesterol + reduced adrenodoxin + O2
? + oxidized adrenodoxin + H2O
show the reaction diagram
-
-
-
-
?
cholesterol + reduced adrenodoxin + O2
pregnenolone + 4-methylpentanal + oxidized adrenodoxin + H2O
show the reaction diagram
cholesterol + reduced adrenodoxin + O2 + H+
pregnenolone + 4-methylpentanal + oxidized adrenodoxin + H2O
show the reaction diagram
-
-
-
-
r
cholesterol + reduced ferredoxin + O2
pregnenolone + 4-methylpentanal + oxidized ferredoxin
show the reaction diagram
cholesterol sulfate + reduced adrenodoxin + O2
pregnenolone sulfate + 17-hydroxy-pregnenolone + dehydroisoandrosterone sulfate + oxidized adrenodoxin + H2O
show the reaction diagram
-
-
-
?
vitamin D2 + reduced adrenodoxin + O2
17,20,24-trihydroxyvitamin D2 + oxidized adrenodoxin + H2O
show the reaction diagram
-
P450scc catalyzes three sequential hydroxylations of D2 producing 20-hydroxyvitamin D2, 17,20-dihydroxyvitamin D2, and 17,20,24-trihydroxyvitamin D2, which dissociate from the active site of P450scc and accumulate in the reaction mixture
-
-
?
vitamin D3 + reduced adrenodoxin + O2
20-hydroxyvitamin D3 + oxidized adrenodoxin + H2O
show the reaction diagram
additional information
?
-