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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)

Inhibitors

Inhibitors on EC 1.14.15.6 - cholesterol monooxygenase (side-chain-cleaving)

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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(20R,S)-20-amino-5-pregnen-3beta-ol
-
20-amine derivative, amine is attached closer to the D-ring than in the 22-amine, very weak inhibitor, 0.1 mM causes less than 20% inhibition
(20S)-22-thiacholesterol
-
competitive inhibitor, is converted enzymatically to a more potent inhibitor, the (22S) and (22R) sulfoxides, inhibition by approximately 75% at 0.001 mM, no inactivation in absence of NADPH and O2
(20S,22R)-22-thiacholesterol S-oxide
-
competitive versus cholesterol, binds 10times more tightly than (22S) diastereomer, 25% and 44% inhibition at 0.00005 mM and 0.0001 mM, respectively, complete inhibition at 0.001 mM, no substrate for P-450
(20S,22S)-22-thiacholesterol S-oxide
-
competitive versus cholesterol, no substrate for P-450
(22R)-22-Aminocholesterol
-
completely inhibited by 0.001 mM, affinity toward the P-450scc almost 3fold greater than that for the (22S) form, competitive versus cholesterol, no substrate for P-450
(22S)-22-Aminocholesterol
-
not inhibited below 0.001 mM, competitive versus cholesterol, no substrate for P-450
17,20-dihydroxyvitamin D2
-
competitive inhibitor
17beta-amino-5-androsten-3beta-ol
-
17-amine derivative, amine is attached closer to the D-ring than in the 22-amine, very weak inhibitor, 0.1 mM causes less than 20% inhibition
22-Amino-23,24-bisnor-5-cholen-3beta-ol
22-amino-23,24-bisnor-5alpha-cholen-3beta-ol
-
50% inhibition at 0.003 mM
23,24-bisnor-5-cholene-3beta,22-diol
-
competitive inhibitor, 40% inhibition at 0.01 mM, 50% at 0.015 mM, resembles the intermediate 22-hydroxycholesterol but acts as an inhibitor rather than serving as a substrate
23-Amino-24-nor-5-cholen-3beta-ol
-
23-amine derivative, same steroid ring structure as cholesterol, competitive inhibitor with respect to cholesterol, 50% inhibition at 0.0001 mM, reversible cooperative binding
24-Amino-5-cholen-3beta-ol
-
24-amine derivative, amine attached in greater distance from steroid ring, same steroid ring structure as cholesterol, causes a progressive decrease in inhibitory potency, 50% inhibition at 0.0023 mM, reversible noncooperative binding
25-Amino-26,27-bisnor-5-cholesten-3beta-ol
-
25-amine derivative, amine attached in greater distance from steroid ring, causes a progressive decrease in inhibitory potency, 50% inhibition at more than 0.1 mM
adrenodoxin
-
oxidized form, high affinity to P-450scc, inhibits side chain cleavage by competition with reduced form
-
aminogluthetimide
-
-
cholesterol
-
inhibition above 0.003 mM, mitochondrial
Cholesterol sulfate
-
inhibition above 0.005 mM, mitochondrial
glycerol
-
substrate cholesterol, 50% inhibition at 25% glycerol, substrate 22(R)-hydroxycholesterol, 50% inhibition at 44% glycerol, substrate 20alpha-hydroxycholesterol, 50% inhibition at 48% glycerol, substrate 20alpha, 22(R)-dihydroxycholesterol, 50% inhibition at 51% glycerol
methoxychlor
-
pesticide of DDT, suicide inhibitor, competitive to cholesterol, substantial irreversible loss of activity, 5% inhibition within 5 min at 0.2 mM, decrease is suppressed by the presence of cholesterol
phosphatidyl choline
-
-
phosphatidyl ethanolamine
-
-
additional information
-