Any feedback?
Information on EC 1.14.15.6 - cholesterol monooxygenase (side-chain-cleaving)
for references in articles please use BRENDA:EC1.14.15.6Please wait a moment until all data is loaded. This message will disappear when all data is loaded.
EC Tree
1.14.15.6 cholesterol monooxygenase (side-chain-cleaving)IUBMB Comments
A heme-thiolate protein (cytochrome P-450). The reaction proceeds in three stages, with two hydroxylations at C-22 and C-20 preceding scission of the side-chain between carbons 20 and 22. The initial source of the electrons is NADPH, which transfers the electrons to the adrenodoxin via EC 1.18.1.6, adrenodoxin-NADP+ reductase.
Specify your search results
Word Map
- 1.14.15.6
-
steroidogenic
-
steroidogenesis
- star
- progesterone
- testosterone
- ovarian
- pregnenolone
-
granulosa
- leydig
- ovary
- follicle
- androgen
- testis
- testicular
- lh
- lutein
- aromatase
- adrenodoxin
- gonad
- cyp17a1
-
adrenocortical
- estradiol
- acth
- cortisol
- gonadotropin
- follicular
-
3beta-hydroxysteroid
- hsd3b1
- 3beta-hsd
-
theca
- androstenedione
- p450arom
- aminoglutethimide
- cyp11b2
-
neurosteroids
-
22r-hydroxycholesterol
- 21-hydroxylase
-
lhcgr
- hsd17b3
-
scarb1
- synthesis
- medicine
- cyp21
-
hcg-stimulated
- biotechnology
-
lipoid
-
fsh-induced
-
11beta-hydroxylase
- srd5a1
-
interrenal
- analysis
- 17alpha-hydroxylase
- drug development
- trilostane
-
fsh-stimulated
The enzyme appears in viruses and cellular organisms
Reaction Schemes
+
6
reduced adrenodoxin
+
3
+
6
=
+
+
6
oxidized adrenodoxin
+
4
Synonyms
p450scc, cyp11a1, cytochrome p-450scc, cytochrome p450scc, cyp11a, cholesterol side-chain cleavage enzyme, p450(scc), cholesterol side chain cleavage enzyme, cholesterol side-chain cleavage cytochrome p450, cytochrome p450 cholesterol side-chain cleavage, 
more
topPlease wait a moment until the data is sorted. This message will disappear when the data is sorted.
SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
C27-side chain cleavage enzyme
-
-
-
-
cholesterol 20-22-desmolase
-
-
-
-
cholesterol C20-22 desmolase
-
-
-
-
cholesterol C20-C22 lyase
-
-
-
-
cholesterol desmolase
-
-
-
-
cholesterol side chain cleavage enzyme
cholesterol side-chain cleavage enzyme
cholesterol side-chain-cleaving enzyme
-
-
-
-
cholesterol side-cleaving enzyme
CYP11A1
CYPXIA1
-
-
-
-
cytochrome P-450scc
-
-
-
-
cytochrome P450 cholesterol side chain cleavage
cytochrome P450 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 cholesterol side-chain cleavage enzyme
P450(scc)
-
-
-
-
P450scc
steroid 20-22 desmolase
-
-
-
-
steroid 20-22-lyase
-
-
-
-
cholesterol side-chain cleavage enzyme
-
-
-
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
(20R,22R)-20,22-dihydroxy-cholesterol + 2 reduced adrenodoxin + O2 + 2 H+ = pregnenolone + 4-methylpentanal + 2 oxidized adrenodoxin + 2 H2O
(1c)
-
-
-
(22R)-22-hydroxycholesterol + 2 reduced adrenodoxin + O2 + 2 H+ = (20R,22R)-20,22-dihydroxycholesterol + 2 oxidized adrenodoxin + H2O
(1b)
-
-
-
cholesterol + 2 reduced adrenodoxin + O2 + 2 H+ = (22R)-22-hydroxycholesterol + 2 oxidized adrenodoxin + H2O
(1a)
-
-
-
cholesterol + 6 reduced adrenodoxin + 3 O2 + 6 H+ = pregnenolone + 4-methylpentanal + 6 oxidized adrenodoxin + 4 H2O
overall reaction
-
-
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
-
-
-
-
redox reaction
-
-
-
-
reduction
-
-
-
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
SYSTEMATIC NAME
IUBMB Comments
cholesterol,reduced-adrenal-ferredoxin:oxygen oxidoreductase (side-chain-cleaving)
A heme-thiolate protein (cytochrome P-450). The reaction proceeds in three stages, with two hydroxylations at C-22 and C-20 preceding scission of the side-chain between carbons 20 and 22. The initial source of the electrons is NADPH, which transfers the electrons to the adrenodoxin via EC 1.18.1.6, adrenodoxin-NADP+ reductase.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
CAS REGISTRY NUMBER
COMMENTARY
37292-81-2
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(20R,22R)-20,22-dihydroxy-cholesterol + 2 reduced adrenodoxin + O2
pregnenolone + 4-methylpentanal + 2 oxidized adrenodoxin + 2 H2O
(20S)-22-thiacholesterol + reduced adrenodoxin + O2
(20S,22R)-22-thiacholesterol S-oxide + (20S,22S)-22-thiacholesterol S-oxide
-
-
(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
17,20-dihydroxyvitamin D2 + reduced adrenodoxin + O2
17,20,24-trihydroxyvitamin D2 + oxidized adrenodoxin + O2
-
is slowly metabolized
-
-
?
20,23-dihydroxyvitamin D3 + reduced adrenodoxin + O2
17,20,23-trihydroxyvitamin D3 + oxidized adrenodoxin + H2O
-
-
-
-
?
20,23-dihydroxyvitamin D3 + reduced adrenodoxin + O2
17alpha,20,23-trihydroxyvitamin D3 + oxidized adrenodoxin + H2O
-
-
-
-
?
20-hydroxyvitamin D2 + reduced adrenodoxin + O2
17,20,24-trihydroxyvitamin D2 + oxidized adrenodoxin + O2
-
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
-
-
-
-
?
20-hydroxyvitamin D3 + reduced adrenodoxin + O2
20,23-dihydroxyvitamin D3 + oxidized adrenodoxin + H2O
-
-
-
-
?
20alpha, 22(R)-dihydroxycholesterol + reduced adrenodoxin + O2
? + oxidized adrenodoxin + H2O
-
-
-
-
?
20alpha-hydroxycholesterol + reduced adrenodoxin + O2
pregnenolone + 4-methylpentanal + oxidized adrenodoxin + H2O
22(R)-hydroxycholesterol + reduced adrenodoxin + O2
pregnenolone + oxidized adrenodoxin + H2O
25-hydroxycholesterol + O2 + reduced ferredoxin
pregnenolone + H2O + ferredoxin + 4-hydroxy-4-methylpentanal
-
-
-
?
25-hydroxycholesterol + reduced adrenodoxin + O2
pregnenolone + oxidized adrenodoxin + H2O
-
-
-
?
cholesterol + 2 reduced adrenodoxin + O2
(22R)-22-hydroxycholesterol + 2 oxidized adrenodoxin + H2O
cholesterol + 6 reduced adrenodoxin + 3 O2
pregnenolone + 4-methylpentanal + 6 oxidized adrenodoxin + 4 H2O
cholesterol + 6 reduced adrenodoxin mutant S112W + 3 O2
pregnenolone + 4-methylpentanal + 6 oxidized adrenodoxin mutant S112W + 4 H2O
-
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
cholesterol + reduced adrenodoxin + O2
pregnenolone + 4-methylpentanal + oxidized adrenodoxin + H2O
cholesterol + reduced adrenodoxin + O2 + H+
pregnenolone + 4-methylpentanal + oxidized adrenodoxin + H2O
-
-
-
-
r
cholesterol + reduced ferredoxin + O2
pregnenolone + 4-methylpentanal + oxidized ferredoxin
cholesterol sulfate + reduced adrenodoxin + O2
pregnenolone sulfate + 17-hydroxy-pregnenolone + dehydroisoandrosterone sulfate + oxidized adrenodoxin + H2O
-
-
-
?
vitamin D2 + reduced adrenodoxin + O2
17,20,24-trihydroxyvitamin D2 + oxidized adrenodoxin + H2O
-
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
-
-
?
(20R,22R)-20,22-dihydroxy-cholesterol + 2 reduced adrenodoxin + O2
pregnenolone + 4-methylpentanal + 2 oxidized adrenodoxin + 2 H2O
-
-
-
?
(20R,22R)-20,22-dihydroxy-cholesterol + 2 reduced adrenodoxin + O2
pregnenolone + 4-methylpentanal + 2 oxidized adrenodoxin + 2 H2O
-
-
-
?
(20R,22R)-20,22-dihydroxy-cholesterol + 2 reduced adrenodoxin + O2
pregnenolone + 4-methylpentanal + 2 oxidized adrenodoxin + 2 H2O
-
-
-
-
?
(20R,22R)-20,22-dihydroxy-cholesterol + 2 reduced adrenodoxin + O2
pregnenolone + 4-methylpentanal + 2 oxidized adrenodoxin + 2 H2O
-
-
-
-
?
(22R)-22-hydroxycholesterol + 2 reduced adrenodoxin + O2
(20R,22R)-20,22-dihydroxycholesterol + 2 oxidized adrenodoxin + H2O
-
-
-
?
(22R)-22-hydroxycholesterol + 2 reduced adrenodoxin + O2
(20R,22R)-20,22-dihydroxycholesterol + 2 oxidized adrenodoxin + H2O
product binding structure analysis, detailed overview
-
-
?
(22R)-22-hydroxycholesterol + 2 reduced adrenodoxin + O2
(20R,22R)-20,22-dihydroxycholesterol + 2 oxidized adrenodoxin + H2O
-
-
-
?
(22R)-22-hydroxycholesterol + 2 reduced adrenodoxin + O2
(20R,22R)-20,22-dihydroxycholesterol + 2 oxidized adrenodoxin + H2O
-
-
-
-
?
(22R)-22-hydroxycholesterol + 2 reduced adrenodoxin + O2
(20R,22R)-20,22-dihydroxycholesterol + 2 oxidized adrenodoxin + H2O
-
-
-
-
?
20alpha-hydroxycholesterol + reduced adrenodoxin + O2
pregnenolone + 4-methylpentanal + oxidized adrenodoxin + H2O
-
-
-
?
20alpha-hydroxycholesterol + reduced adrenodoxin + O2
pregnenolone + 4-methylpentanal + oxidized adrenodoxin + H2O
-
-
-
-
?
22(R)-hydroxycholesterol + reduced adrenodoxin + O2
? + oxidized adrenodoxin + H2O
-
-
-
-
?
22(R)-hydroxycholesterol + reduced adrenodoxin + O2
? + oxidized adrenodoxin + H2O
-
mitochondria containing the AAC-mCYP11A1 hybrid have the highest cholesterol side-chain cleavage activity in the reconstituted system. Ad-mCYP11A1 hybrid demonstrates only residual enzyme activity
-
-
?
22(R)-hydroxycholesterol + reduced adrenodoxin + O2
pregnenolone + oxidized adrenodoxin + H2O
-
-
-
-
?
22(R)-hydroxycholesterol + reduced adrenodoxin + O2
pregnenolone + oxidized adrenodoxin + H2O
-
-
-
-
?
cholesterol + 2 reduced adrenodoxin + O2
(22R)-22-hydroxycholesterol + 2 oxidized adrenodoxin + H2O
-
-
-
?
cholesterol + 2 reduced adrenodoxin + O2
(22R)-22-hydroxycholesterol + 2 oxidized adrenodoxin + H2O
-
-
-
-
?
cholesterol + 2 reduced adrenodoxin + O2
(22R)-22-hydroxycholesterol + 2 oxidized adrenodoxin + H2O
-
-
-
-
?
cholesterol + 6 reduced adrenodoxin + 3 O2
pregnenolone + 4-methylpentanal + 6 oxidized adrenodoxin + 4 H2O
-
-
-
?
cholesterol + 6 reduced adrenodoxin + 3 O2
pregnenolone + 4-methylpentanal + 6 oxidized adrenodoxin + 4 H2O
-
-
precursor of all steroid hormones
?
cholesterol + 6 reduced adrenodoxin + 3 O2
pregnenolone + 4-methylpentanal + 6 oxidized adrenodoxin + 4 H2O
-
-
precursor of all steroid hormones
?
cholesterol + 6 reduced adrenodoxin + 3 O2
pregnenolone + 4-methylpentanal + 6 oxidized adrenodoxin + 4 H2O
-
-
precursor of all steroid hormones
?
cholesterol + 6 reduced adrenodoxin + 3 O2
pregnenolone + 4-methylpentanal + 6 oxidized adrenodoxin + 4 H2O
-
-
precursor of all steroid hormones
?
cholesterol + 6 reduced adrenodoxin + 3 O2
pregnenolone + 4-methylpentanal + 6 oxidized adrenodoxin + 4 H2O
-
-
isocapraldehyde additional product
?
cholesterol + 6 reduced adrenodoxin + 3 O2
pregnenolone + 4-methylpentanal + 6 oxidized adrenodoxin + 4 H2O
-
first step in biosynthesis of all steroid hormones
-
?
cholesterol + 6 reduced adrenodoxin + 3 O2
pregnenolone + 4-methylpentanal + 6 oxidized adrenodoxin + 4 H2O
-
first step in biosynthesis of all steroid hormones
-
?
cholesterol + 6 reduced adrenodoxin + 3 O2
pregnenolone + 4-methylpentanal + 6 oxidized adrenodoxin + 4 H2O
-
first step in biosynthesis of all steroid hormones
-
?
cholesterol + 6 reduced adrenodoxin + 3 O2
pregnenolone + 4-methylpentanal + 6 oxidized adrenodoxin + 4 H2O
-
first step in biosynthesis of all steroid hormones
-
?
cholesterol + 6 reduced adrenodoxin + 3 O2
pregnenolone + 4-methylpentanal + 6 oxidized adrenodoxin + 4 H2O
-
first step in biosynthesis of all steroid hormones
-
?
cholesterol + 6 reduced adrenodoxin + 3 O2
pregnenolone + 4-methylpentanal + 6 oxidized adrenodoxin + 4 H2O
-
first step in biosynthesis of all steroid hormones
-
?
cholesterol + 6 reduced adrenodoxin + 3 O2
pregnenolone + 4-methylpentanal + 6 oxidized adrenodoxin + 4 H2O
-
first step in biosynthesis of all steroid hormones
-
?
cholesterol + 6 reduced adrenodoxin + 3 O2
pregnenolone + 4-methylpentanal + 6 oxidized adrenodoxin + 4 H2O
-
first step in biosynthesis of all steroid hormones
-
?
cholesterol + 6 reduced adrenodoxin + 3 O2
pregnenolone + 4-methylpentanal + 6 oxidized adrenodoxin + 4 H2O
-
first step in biosynthesis of all steroid hormones
isocapraldehyde additional product
?
cholesterol + 6 reduced adrenodoxin + 3 O2
pregnenolone + 4-methylpentanal + 6 oxidized adrenodoxin + 4 H2O
-
first step in biosynthesis of all steroid hormones
isocaproic aldehyde additional product
?
cholesterol + 6 reduced adrenodoxin + 3 O2
pregnenolone + 4-methylpentanal + 6 oxidized adrenodoxin + 4 H2O
overall reaction
-
-
?
cholesterol + 6 reduced adrenodoxin + 3 O2
pregnenolone + 4-methylpentanal + 6 oxidized adrenodoxin + 4 H2O
-
overall reaction
-
-
?
cholesterol + 6 reduced adrenodoxin + 3 O2
pregnenolone + 4-methylpentanal + 6 oxidized adrenodoxin + 4 H2O
-
overall reaction
-
-
?
cholesterol + 6 reduced adrenodoxin + 3 O2
pregnenolone + 4-methylpentanal + 6 oxidized adrenodoxin + 4 H2O
-
overall reaction
-
-
?
cholesterol + reduced adrenal ferredoxin + O2
pregnenolone + 4-methylpentanal + oxidized adrenal ferredoxin
-
-
-
-
?
cholesterol + reduced adrenal ferredoxin + O2
pregnenolone + 4-methylpentanal + oxidized adrenal ferredoxin
-
-
-
-
?
cholesterol + reduced adrenal ferredoxin + O2
pregnenolone + 4-methylpentanal + oxidized adrenal ferredoxin
-
-
-
-
?
cholesterol + reduced adrenal ferredoxin + O2
pregnenolone + 4-methylpentanal + oxidized adrenal ferredoxin
-
-
-
?
cholesterol + reduced adrenal ferredoxin + O2
pregnenolone + 4-methylpentanal + oxidized adrenal ferredoxin
-
first and rate-limiting enzyme in adrenal steroidogenesis
-
-
?
cholesterol + reduced adrenal ferredoxin + O2
pregnenolone + 4-methylpentanal + oxidized adrenal ferredoxin
-
-
-
-
?
cholesterol + reduced adrenodoxin + O2
pregnenolone + 4-methylpentanal + oxidized adrenodoxin + H2O
-
-
-
?
cholesterol + reduced adrenodoxin + O2
pregnenolone + 4-methylpentanal + oxidized adrenodoxin + H2O
-
-
-
?
cholesterol + reduced adrenodoxin + O2
pregnenolone + 4-methylpentanal + oxidized adrenodoxin + H2O
-
-
-
?
cholesterol + reduced adrenodoxin + O2
pregnenolone + 4-methylpentanal + oxidized adrenodoxin + H2O
-
-
-
?
cholesterol + reduced adrenodoxin + O2
pregnenolone + 4-methylpentanal + oxidized adrenodoxin + H2O
-
-
-
?
cholesterol + reduced adrenodoxin + O2
pregnenolone + 4-methylpentanal + oxidized adrenodoxin + H2O
-
-
-
?
cholesterol + reduced adrenodoxin + O2
pregnenolone + 4-methylpentanal + oxidized adrenodoxin + H2O
-
-
-
?
cholesterol + reduced adrenodoxin + O2
pregnenolone + 4-methylpentanal + oxidized adrenodoxin + H2O
-
-
-
?
cholesterol + reduced adrenodoxin + O2
pregnenolone + 4-methylpentanal + oxidized adrenodoxin + H2O
-
-
-
?
cholesterol + reduced adrenodoxin + O2
pregnenolone + 4-methylpentanal + oxidized adrenodoxin + H2O
-
-
-
?
cholesterol + reduced adrenodoxin + O2
pregnenolone + 4-methylpentanal + oxidized adrenodoxin + H2O
-
-
-
?
cholesterol + reduced adrenodoxin + O2
pregnenolone + 4-methylpentanal + oxidized adrenodoxin + H2O
-
-
-
?
cholesterol + reduced adrenodoxin + O2
pregnenolone + 4-methylpentanal + oxidized adrenodoxin + H2O
-
-
-
?
cholesterol + reduced adrenodoxin + O2
pregnenolone + 4-methylpentanal + oxidized adrenodoxin + H2O
-
-
-
?
cholesterol + reduced adrenodoxin + O2
pregnenolone + 4-methylpentanal + oxidized adrenodoxin + H2O
-
-
-
?
cholesterol + reduced adrenodoxin + O2
pregnenolone + 4-methylpentanal + oxidized adrenodoxin + H2O
-
-
-
?
cholesterol + reduced adrenodoxin + O2
pregnenolone + 4-methylpentanal + oxidized adrenodoxin + H2O
-
-
-
-
?
cholesterol + reduced adrenodoxin + O2
pregnenolone + 4-methylpentanal + oxidized adrenodoxin + H2O
-
-
isocaproaldehyde produced besides
?
cholesterol + reduced adrenodoxin + O2
pregnenolone + 4-methylpentanal + oxidized adrenodoxin + H2O
-
intermediates (22R)-22-hydroxycholesterol and (20R,22R)-20,22-dihydroxycholesterol from hydroxylation
-
?
cholesterol + reduced adrenodoxin + O2
pregnenolone + 4-methylpentanal + oxidized adrenodoxin + H2O
-
intermediates (22R)-22-hydroxycholesterol and (20R,22R)-20,22-dihydroxycholesterol from hydroxylation
-
?
cholesterol + reduced adrenodoxin + O2
pregnenolone + 4-methylpentanal + oxidized adrenodoxin + H2O
-
20- or 22-hydroxycholesterol and 20,22-dehydroxycholesterol are putative intermediates
-
?
cholesterol + reduced adrenodoxin + O2
pregnenolone + 4-methylpentanal + oxidized adrenodoxin + H2O
-
regioselective and stereospecific transformation
-
?
cholesterol + reduced adrenodoxin + O2
pregnenolone + 4-methylpentanal + oxidized adrenodoxin + H2O
-
intermediates 22R-hydroxycholesterol and 20alpha,22R-dihydroxycholesterol from hydroxylation
-
?
cholesterol + reduced adrenodoxin + O2
pregnenolone + 4-methylpentanal + oxidized adrenodoxin + H2O
-
without demonstrable accumulation of putative intermediates 20alpha-hydroxycholesterol and 20alpha,22-dehydroxycholesterol
-
?
cholesterol + reduced adrenodoxin + O2
pregnenolone + 4-methylpentanal + oxidized adrenodoxin + H2O
-
stable intermediates: 22-hydroxycholesterol and 20,22-dihydroxycholesterol
-
?
cholesterol + reduced adrenodoxin + O2
pregnenolone + 4-methylpentanal + oxidized adrenodoxin + H2O
-
hydroxylation of cholesterol at C-22, then C-20, followed by oxidative scission of the glycol to get pregnenolone
-
?
cholesterol + reduced adrenodoxin + O2
pregnenolone + 4-methylpentanal + oxidized adrenodoxin + H2O
-
-
-
-
?
cholesterol + reduced adrenodoxin + O2
pregnenolone + 4-methylpentanal + oxidized adrenodoxin + H2O
-
-
-
-
?
cholesterol + reduced adrenodoxin + O2
pregnenolone + 4-methylpentanal + oxidized adrenodoxin + H2O
-
-
-
-
?
cholesterol + reduced ferredoxin + O2
pregnenolone + 4-methylpentanal + oxidized ferredoxin
-
-
-
-
?
cholesterol + reduced ferredoxin + O2
pregnenolone + 4-methylpentanal + oxidized ferredoxin
-
metabolic regulation of enzyme expression, overview
-
-
?
cholesterol + reduced ferredoxin + O2
pregnenolone + 4-methylpentanal + oxidized ferredoxin
-
the catalyzed reaction is not the rate-limiting step in steroidogenesis except in placenta which lacks the steroidogenic acute regulatory protein, overview, enzyme deficiency by mutations leads to severe disorders, overview
-
-
?
cholesterol + reduced ferredoxin + O2
pregnenolone + 4-methylpentanal + oxidized ferredoxin
-
the enzyme is a cytochrome P450 enzyme, the enzyme structure possesses a substrate access channel, which is responsible for regioselectivity of the enzyme together with residue F202
-
-
?
vitamin D3 + reduced adrenodoxin + O2
20-hydroxyvitamin D3 + oxidized adrenodoxin + H2O
-
-
when incubated in 0.45% cyclodextrin, 20-hydroxyvitamin D3 is the major product of vitamin D3 metabolism by P450scc. The second major product is 20,23-dihydroxyvitamin D3. Major products dissociate from the P450scc active site and accumulate at a concentration well above the P450scc concentration
-
?
vitamin D3 + reduced adrenodoxin + O2
20-hydroxyvitamin D3 + oxidized adrenodoxin + H2O
-
is hydroxylated with lower efficiency than cholesterol
-
-
?
additional information
?
-
-
cholesterol side chain cleavage activity is dependent on free reduced adrenodoxin
-
-
?
additional information
?
-
-
21 amino-acid residues from Pro-8 to Arg-28 in the amino-terminus are located in or near the cholesterol-binding site, this site is in a quite different region from the adreno-ferredoxin binding site Pro374 to Iso-389
-
-
?
additional information
?
-
-
electron shuttle between flavoprotein and cytochrome, biphasic reduction kinetics, rapid association of cytochrome and adrenodoxin, slower intracomplex electron transfer from iron-sulfur center of adrenodoxin to heme of cytochrome P-450scc
-
-
?
additional information
?
-
-
suggested shuttle mechanism in which adrenodoxin transfers electrons between adrenodoxin reductase and cytochrome P-450. No ternary adrenodoxin-adrenodoxin reductase-P-450 complex
-
-
?
additional information
?
-
-
suggested shuttle mechanism in which adrenodoxin transfers electrons between adrenodoxin reductase and cytochrome P-450. No ternary adrenodoxin-adrenodoxin reductase-P-450 complex
-
-
?
additional information
?
-
-
suggested shuttle mechanism in which adrenodoxin transfers electrons between adrenodoxin reductase and cytochrome P-450. No ternary adrenodoxin-adrenodoxin reductase-P-450 complex
-
-
?
additional information
?
-
-
suggested shuttle mechanism in which adrenodoxin transfers electrons between adrenodoxin reductase and cytochrome P-450. No ternary adrenodoxin-adrenodoxin reductase-P-450 complex
-
-
?
additional information
?
-
-
transfer of cholesterol to cytochrome P-450scc is rate-limiting
-
-
?
additional information
?
-
-
3 high regioselective and stereospecific oxidation steps at the same heme active site
-
-
?
additional information
?
-
-
dissociation of oxidized adrenodoxin from P-450scc must be a potential rate-limiting factor
-
-
?
additional information
?
-
-
dissociation of oxidized adrenodoxin from P-450scc must be a potential rate-limiting factor
-
-
?
additional information
?
-
-
reduction of adrenodoxin must be rate-limiting step
-
-
?
additional information
?
-
-
2 interaction processes with 2 different sensitivities to ionic strength
-
-
?
additional information
?
-
-
the enzyme is important in steroidogenesis, regulatory mechanism, overview
-
-
?
additional information
?
-
-
the enzyme is important in steroidogenesis, regulatory mechanism, overview
-
-
?
additional information
?
-
-
leptin interferes with adrenocorticotropin/cAMP signaling, possibly through a janus kinase 2-phosphatidylinositol 3-kinase/akt-phosphodiesterase 3-cAMP pathway, to down-regulate cholesterol side-chain cleavage cytochrome P450 enzyme in human adrenocortical NCI-H295 cell line, mechanism, overview
-
-
?
additional information
?
-
-
cytochrome P450scc metabolizes vitamin D3 to 20-hydroxyvitamin D3 and 20,23-dihydroxyvitamin D3, as well as 1-hydroxyvitamin D3 to 1alpha,20-dihydroxyvitamin D3. It also cleaves the side chain of 7-dehydrocholesterol producing 7-dehydropregnenolone, which can be transformed to 20-hydroxy-7-dehydropregnenolone
-
-
?
additional information
?
-
compound I, i.e. ferryl porphyrin pi-cation radical, is the active species in each of the three sequential monooxygenation reactions by which P450scc catalytically converts Ch to pregnenolone
-
-
?
additional information
?
-
-
the enzyme is a key enzyme in brain steroidogenesis
-
-
?
additional information
?
-
-
the enzyme is important in steroidogenesis, regulatory mechanism, overview
-
-
?
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(20R,22R)-20,22-dihydroxy-cholesterol + 2 reduced adrenodoxin + O2
pregnenolone + 4-methylpentanal + 2 oxidized adrenodoxin + 2 H2O
(22R)-22-hydroxycholesterol + 2 reduced adrenodoxin + O2
(20R,22R)-20,22-dihydroxycholesterol + 2 oxidized adrenodoxin + H2O
cholesterol + 2 reduced adrenodoxin + O2
(22R)-22-hydroxycholesterol + 2 oxidized adrenodoxin + H2O
cholesterol + 6 reduced adrenodoxin + 3 O2
pregnenolone + 4-methylpentanal + 6 oxidized adrenodoxin + 4 H2O
cholesterol + reduced adrenal ferredoxin + O2
pregnenolone + 4-methylpentanal + oxidized adrenal ferredoxin
cholesterol + reduced ferredoxin + O2
pregnenolone + 4-methylpentanal + oxidized ferredoxin
(20R,22R)-20,22-dihydroxy-cholesterol + 2 reduced adrenodoxin + O2
pregnenolone + 4-methylpentanal + 2 oxidized adrenodoxin + 2 H2O
-
-
-
?
(20R,22R)-20,22-dihydroxy-cholesterol + 2 reduced adrenodoxin + O2
pregnenolone + 4-methylpentanal + 2 oxidized adrenodoxin + 2 H2O
-
-
-
-
?
(20R,22R)-20,22-dihydroxy-cholesterol + 2 reduced adrenodoxin + O2
pregnenolone + 4-methylpentanal + 2 oxidized adrenodoxin + 2 H2O
-
-
-
-
?
(22R)-22-hydroxycholesterol + 2 reduced adrenodoxin + O2
(20R,22R)-20,22-dihydroxycholesterol + 2 oxidized adrenodoxin + H2O
-
-
-
?
(22R)-22-hydroxychole