1.14.15.16: vitamin D3 24-hydroxylase
This is an abbreviated version!
For detailed information about vitamin D3 24-hydroxylase, go to the full flat file.
Word Map on EC 1.14.15.16
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1.14.15.16
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cyp24a1
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parathyroid
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1alpha-hydroxylase
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rickets
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24,25-dihydroxyvitamin
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hypercalcemia
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24-hydroxylation
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retinoids
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d-dependent
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1alpha,25oh2d3
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osteocalcin
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vdres
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d-deficient
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1-hydroxylase
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d-responsive
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1,25-dihydroxycholecalciferol
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hyperparathyroidism
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ketoconazole
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nephrocalcinosis
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alopecia
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vdr-mediated
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hypophosphatemic
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d-binding
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1,25oh2d3-induced
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extrarenal
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hypercalciuria
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cholecalciferol
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25-hydroxycholecalciferol
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calcemic
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1alpha-ohase
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alpha-hydroxyvitamin
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calcidiol
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d-resistant
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d3-1alpha-hydroxylase
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osteomalacia
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d-replete
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secosteroid
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hvdrr
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sodium-phosphate
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medicine
- 1.14.15.16
- cyp24a1
- parathyroid
-
1alpha-hydroxylase
- rickets
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24,25-dihydroxyvitamin
- hypercalcemia
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24-hydroxylation
-
retinoids
-
d-dependent
-
1alpha,25oh2d3
- osteocalcin
-
vdres
-
d-deficient
- 1-hydroxylase
-
d-responsive
- 1,25-dihydroxycholecalciferol
- hyperparathyroidism
- ketoconazole
- nephrocalcinosis
- alopecia
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vdr-mediated
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hypophosphatemic
-
d-binding
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1,25oh2d3-induced
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extrarenal
-
hypercalciuria
- cholecalciferol
- 25-hydroxycholecalciferol
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calcemic
- 1alpha-ohase
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alpha-hydroxyvitamin
- calcidiol
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d-resistant
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d3-1alpha-hydroxylase
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osteomalacia
-
d-replete
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secosteroid
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hvdrr
-
sodium-phosphate
- medicine
Reaction
+ 2 reduced adrenodoxin + 2 H+ + = + 2 oxidized adrenodoxin +
Synonyms
1,25-(OH)2D3-24-hydroxylase, 1,25-dihydroxyvitamin D3 24-hydroxylase, 1alpha,25-dihydroxyvitamin D3 24-hydroxylase, 24-hydroxylase, 24-OHase, 24OHase, 25-hydroxyvitamin D-24-hydroxylase, 25-hydroxyvitamin D3-24-hydroxylase, 25-OH-D3-24-hydroxylase, CYP24A1, cytochrome P450 24A1, EC 1.14.13.126, P450cc24, vitamin D 24-hydroxylase, vitamin D-24-hydroxylase
ECTree
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Substrates Products
Substrates Products on EC 1.14.15.16 - vitamin D3 24-hydroxylase
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REACTION DIAGRAM
1alpha,23,25-trihydroxyvitamin D3 + NADPH + H+ + O2
1alpha,25-dihydroxyvitamin D3-26,23-lactone + NADP+ + H2O
1alpha,25-dihydroxyvitamin D3 + NADPH + H+ + O2
1alpha,23,25-trihydroxyvitamin D3 + 25,26,27-trinor-23-ene-1alpha-hydroxyvitamin D3 + NADP+ + H2O
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after hydrogen abstraction of the C-23 position of 1alpha,25-dihydroxyvitamin D3, part of the substrate-radical intermediate is converted into 25,26,27-trinor-23-ene-1alpha-hydroxyvitamin D3, while a major part of them is converted into 1alpha,23,25-trihydroxyvitamin D3
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-
?
1alpha,25-dihydroxyvitamin D3 + NADPH + H+ + O2
1alpha,23,25-trihydroxyvitamin D3 + NADP+ + H2O
1alpha,25-dihydroxyvitamin D3 + NADPH + H+ + O2
1alpha,23S,25,26-tetrahydroxyvitamin D3 + 1alpha,23S,25-trihydroxyvitamin D3 + 25,26,27-trinor-23-ene-1alpha-hydroxyvitamin D3 + NADP+ + H2O
1alpha,25-dihydroxyvitamin D3 + NADPH + H+ + O2
1alpha,24(R)-dihydroxyvitamin D3 + NADP+ + H2O
1alpha,25-dihydroxyvitamin D3 + NADPH + H+ + O2
1alpha,24,25-trihydroxyvitamin D3 + NADP+ + H2O
-
-
-
-
?
1alpha,25-dihydroxyvitamin D3 + NADPH + H+ + O2
1alpha,24R,25-trihydroxyvitamin D3 + NADP+ + H2O
1alpha,25-dihydroxyvitamin D3 + NADPH + H+ + O2
1alpha,25-dihydroxyvitamin D3-26,23-lactone + NADP+ + H2O
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C23-hydroxylation
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-
?
1alpha,25-dihydroxyvitamin D3 + NADPH + H+ + O2
24-oxo-1,23,25-trihydroxyvitamin D3 + 24,25,26,27-tetranor-1,23-dihydroxyvitamin D3 + 1alpha,24R,25-trihydroxyvitamin D3 + 24-oxo-1,25-dihydroxyvitamin D3 + NADP+ + H2O
1alpha-hydroxyvitamin D2 + NADPH + H+ + O2
1alpha,24-dihydroxyvitamin D2 + 1alpha,25-dihydroxyvitamin D2 + 26-carboxy-1alpha,24-dihydroxyvitamin D2 + NADP+ + H2O
2-methylene-19-nor-(20R)-1,25-dihydroxyvitamin D3 + NADPH + H+ + O2
? + NADP+ + H2O
-
-
-
-
?
2-methylene-19-nor-(20S)-1,25-dihydroxyvitamin D3 + NADPH + H+ + O2
? + NADP+ + H2O
-
-
-
-
?
23-oxo-24,25,26,27-tetranor-1alpha-hydroxyvitamin D3 + 2 reduced adrenodoxin + 2 H+ + O2
calcitroic acid + 2 oxidized adrenodoxin + H2O
24,25,26,27-tetranor-1alpha,23-dihydroxyvitamin D3 + 2 reduced adrenodoxin + 2 H+ + O2
23-oxo-24,25,26,27-tetranor-1alpha-hydroxyvitamin D3 + 2 oxidized adrenodoxin + H2O
24-oxo-1alpha,23,25-trihydroxyvitamin D3 + 2 reduced adrenodoxin + 2 H+ + O2
24,25,26,27-tetranor-1alpha,23-dihydroxyvitamin D3 + 2 oxidized adrenodoxin + H2O
24-oxo-1alpha,25-dihydroxyvitamin D3 + 2 reduced adrenodoxin + 2 H+ + O2
24-oxo-1alpha,23,25-trihydroxyvitamin D3 + 2 oxidized adrenodoxin + H2O
25-hydroxyvitamin D3 + NADPH + H+ + O2
1alpha,25-dihydroxyvitamin D3-26,23-lactone + NADP+ + H2O
25-hydroxyvitamin D3 + NADPH + H+ + O2
24,25,26,27-tetranor-23-hydroxyvitamin-D3 + NADP+ + H2O
-
-
-
-
?
25-hydroxyvitamin D3 + NADPH + H+ + O2
24,25-dihydroxyvitamin D3 + NADP+ + H2O
-
-
-
-
?
25-hydroxyvitamin D3 + NADPH + H+ + O2
24-oxo-25-hydroxyvitamin D3 + 23(S),25-dihydroxyvitamin D3 + 24(R),25-dihydroxyvitamin D3 + 24-oxo-23(S),25-dihydoxyvitamin D3 + NADP+ + H2O
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-
-
-
?
25-hydroxyvitamin D3 + NADPH + H+ + O2
25,26,27-trinor-23-ene-vitamin D3 + NADP+ + H2O
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-
the metabolite 25,26,27-trinor-23-ene-vitamin D3 is closely related with the C-23 hydroxylation pathway
-
?
3-epi-1alpha,23,25-trihydroxy-24-oxo-vitamin D3 + 2 reduced adrenodoxin + 2 H+ + O2
3-epi-1alpha,23-dihydroxy-24,25,26,27-tetranor-vitamin D3 + 2 oxidized adrenodoxin + H2O
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-
-
?
3-epi-1alpha,23,25-trihydroxyvitamin D3 + 2 reduced adrenodoxin + 2 H+ + O2
3-epi-1alpha,23,26-trihydroxyvitamin D3 + 2 oxidized adrenodoxin + H2O
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-
-
?
3-epi-1alpha,23,25-trihydroxyvitamin D3 + 2 reduced adrenodoxin + 2 H+ + O2
3-epi-1alpha,25-dihydroxy-23-oxovitamin D3 + 2 oxidized adrenodoxin + H2O
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-
-
?
3-epi-1alpha,23-dihydroxy-24,25,26,27-tetranor-vitamin D3 + 2 reduced adrenodoxin + 2 H+ + O2
3-epicalcitroic acid + 2 oxidized adrenodoxin + H2O
-
-
-
?
3-epi-1alpha,24,25-trihydroxyvitamin D3 + 2 reduced adrenodoxin + 2 H+ + O2
3-epi-1alpha,25-dihydroxy-24-oxo-vitamin D3 + 2 oxidized adrenodoxin + H2O
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-
-
?
3-epi-1alpha,25-dihydroxy-24-oxo-vitamin D3 + 2 reduced adrenodoxin + 2 H+ + O2
3-epi-1alpha,23,25-trihydroxy-24-oxo-vitamin D3 + 2 oxidized adrenodoxin + H2O
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-
-
?
3-epi-1alpha,25-dihydroxyvitamin D3 + 2 reduced adrenodoxin + 2 H+ + O2
3-epi-1alpha,23,25-trihydroxyvitamin D3 + 2 oxidized adrenodoxin + H2O
-
-
-
?
3-epi-1alpha,25-dihydroxyvitamin D3 + 2 reduced adrenodoxin + 2 H+ + O2
3-epi-1alpha,24,25-trihydroxyvitamin D3 + 2 oxidized adrenodoxin + H2O
-
-
-
?
3-epi-1alpha,25-dihydroxyvitamin D3 + 2 reduced adrenodoxin + 2 H+ + O2
3-epi-25,26,27-trinor-23-ene-1alpha-hydroxyvitamin D3 + 2 oxidized adrenodoxin + H2O
-
-
-
?
3-epi-25,26,27-trinor-23-ene-1alpha-hydroxyvitamin D3 + 2 reduced adrenodoxin + 2 H+ + O2
3-epi-25,26,27-trinor-23,24-epoxide-1alpha-hydroxyvitamin D3 + 2 oxidized adrenodoxin + H2O
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-
-
?
calcitetrol + 2 reduced adrenodoxin + 2 H+ + O2
24-oxo-1alpha,25-dihydroxyvitamin D3 + 2 oxidized adrenodoxin + H2O
1alpha,25-dihydroxyvitamin D3-26,23-lactone + NADP+ + H2O
-
-
-
-
?
1alpha,23,25-trihydroxyvitamin D3 + NADPH + H+ + O2
1alpha,25-dihydroxyvitamin D3-26,23-lactone + NADP+ + H2O
-
-
-
-
?
?
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i.e. tacalcitol, hydroxylation occurs at C-25
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-
?
1alpha,24(R)-dihydroxyvitamin D3 + NADPH + H+ + O2
?
-
i.e. tacalcitol, hydroxylation occurs at C-25
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-
?
calcitroic acid + NADP+ + ?
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-
-
-
?
1alpha,24R,25-trihydroxyvitamin D3 + NADPH + O2
calcitroic acid + NADP+ + ?
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-
-
-
?
1alpha,23,25-trihydroxyvitamin D3 + NADP+ + H2O
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-
-
-
?
1alpha,25-dihydroxyvitamin D3 + NADPH + H+ + O2
1alpha,23,25-trihydroxyvitamin D3 + NADP+ + H2O
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-
-
-
?
1alpha,23S,25,26-tetrahydroxyvitamin D3 + 1alpha,23S,25-trihydroxyvitamin D3 + 25,26,27-trinor-23-ene-1alpha-hydroxyvitamin D3 + NADP+ + H2O
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the C-23 oxidation pathway
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-
?
1alpha,25-dihydroxyvitamin D3 + NADPH + H+ + O2
1alpha,23S,25,26-tetrahydroxyvitamin D3 + 1alpha,23S,25-trihydroxyvitamin D3 + 25,26,27-trinor-23-ene-1alpha-hydroxyvitamin D3 + NADP+ + H2O
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the C-23 oxidation pathway, which is almost not shown by rat CYP24A1
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-
?
1alpha,24(R)-dihydroxyvitamin D3 + NADP+ + H2O
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1alpha,25-dihydroxyvitamin D3 is calcitriol
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-
?
1alpha,25-dihydroxyvitamin D3 + NADPH + H+ + O2
1alpha,24(R)-dihydroxyvitamin D3 + NADP+ + H2O
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1alpha,25-dihydroxyvitamin D3 is calcitriol
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-
?
1alpha,24R,25-trihydroxyvitamin D3 + NADP+ + H2O
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-
-
-
?
1alpha,25-dihydroxyvitamin D3 + NADPH + H+ + O2
1alpha,24R,25-trihydroxyvitamin D3 + NADP+ + H2O
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C24-hydroxylation, the preferred pathway of human CYP24A1
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-
?
1alpha,25-dihydroxyvitamin D3 + NADPH + H+ + O2
1alpha,24R,25-trihydroxyvitamin D3 + NADP+ + H2O
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-
-
-
?
1alpha,25-dihydroxyvitamin D3 + NADPH + H+ + O2
1alpha,24R,25-trihydroxyvitamin D3 + NADP+ + H2O
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-
-
-
?
24-oxo-1,23,25-trihydroxyvitamin D3 + 24,25,26,27-tetranor-1,23-dihydroxyvitamin D3 + 1alpha,24R,25-trihydroxyvitamin D3 + 24-oxo-1,25-dihydroxyvitamin D3 + NADP+ + H2O
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the C-24 oxidation pathway
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-
?
1alpha,25-dihydroxyvitamin D3 + NADPH + H+ + O2
24-oxo-1,23,25-trihydroxyvitamin D3 + 24,25,26,27-tetranor-1,23-dihydroxyvitamin D3 + 1alpha,24R,25-trihydroxyvitamin D3 + 24-oxo-1,25-dihydroxyvitamin D3 + NADP+ + H2O
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the C-24 oxidation pathway
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-
?
calcitroic acid + NADP+ + ?
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-
-
-
?
1alpha,25-dihydroxyvitamin D3 + NADPH + H+ + O2
calcitroic acid + NADP+ + ?
-
-
-
-
?
1alpha,24-dihydroxyvitamin D2 + 1alpha,25-dihydroxyvitamin D2 + 26-carboxy-1alpha,24-dihydroxyvitamin D2 + NADP+ + H2O
-
-
-
-
?
1alpha-hydroxyvitamin D2 + NADPH + H+ + O2
1alpha,24-dihydroxyvitamin D2 + 1alpha,25-dihydroxyvitamin D2 + 26-carboxy-1alpha,24-dihydroxyvitamin D2 + NADP+ + H2O
-
-
-
-
?
calcitroic acid + 2 oxidized adrenodoxin + H2O
-
-
-
?
23-oxo-24,25,26,27-tetranor-1alpha-hydroxyvitamin D3 + 2 reduced adrenodoxin + 2 H+ + O2
calcitroic acid + 2 oxidized adrenodoxin + H2O
-
-
-
?
23-oxo-24,25,26,27-tetranor-1alpha-hydroxyvitamin D3 + 2 oxidized adrenodoxin + H2O
-
-
-
?
24,25,26,27-tetranor-1alpha,23-dihydroxyvitamin D3 + 2 reduced adrenodoxin + 2 H+ + O2
23-oxo-24,25,26,27-tetranor-1alpha-hydroxyvitamin D3 + 2 oxidized adrenodoxin + H2O
-
-
-
?
24,25,26,27-tetranor-1alpha,23-dihydroxyvitamin D3 + 2 oxidized adrenodoxin + H2O
-
-
-
?
24-oxo-1alpha,23,25-trihydroxyvitamin D3 + 2 reduced adrenodoxin + 2 H+ + O2
24,25,26,27-tetranor-1alpha,23-dihydroxyvitamin D3 + 2 oxidized adrenodoxin + H2O
-
-
-
?
24-oxo-1alpha,23,25-trihydroxyvitamin D3 + 2 oxidized adrenodoxin + H2O
-
-
-
?
24-oxo-1alpha,25-dihydroxyvitamin D3 + 2 reduced adrenodoxin + 2 H+ + O2
24-oxo-1alpha,23,25-trihydroxyvitamin D3 + 2 oxidized adrenodoxin + H2O
-
-
-
?
1alpha,25-dihydroxyvitamin D3-26,23-lactone + NADP+ + H2O
-
C-23 hydroxylation
-
-
?
25-hydroxyvitamin D3 + NADPH + H+ + O2
1alpha,25-dihydroxyvitamin D3-26,23-lactone + NADP+ + H2O
-
-
-
-
?
24R,25-dihydroxyvitamin D3 + NADP+ + H2O
-
-
-
-
?
25-hydroxyvitamin D3 + NADPH + H+ + O2
24R,25-dihydroxyvitamin D3 + NADP+ + H2O
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C-24 hydroxylation
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-
?
25-hydroxyvitamin D3 + NADPH + H+ + O2
24R,25-dihydroxyvitamin D3 + NADP+ + H2O
-
-
-
-
?
25-hydroxyvitamin D3 + NADPH + H+ + O2
24R,25-dihydroxyvitamin D3 + NADP+ + H2O
-
-
-
-
?
secalciferol + 2 oxidized adrenodoxin + H2O
-
-
-
?
calcidiol + 2 reduced adrenodoxin + 2 H+ + O2
secalciferol + 2 oxidized adrenodoxin + H2O
-
-
-
-
?
24-oxo-1alpha,25-dihydroxyvitamin D3 + 2 oxidized adrenodoxin + H2O
-
-
-
?
calcitetrol + 2 reduced adrenodoxin + 2 H+ + O2
24-oxo-1alpha,25-dihydroxyvitamin D3 + 2 oxidized adrenodoxin + H2O
-
-
-
-
?
calcitetrol + 2 reduced adrenodoxin + 2 H+ + O2
24-oxo-1alpha,25-dihydroxyvitamin D3 + 2 oxidized adrenodoxin + H2O
-
-
-
?
calcitetrol + 2 oxidized adrenodoxin + H2O
-
-
-
?
calcitriol + 2 reduced adrenodoxin + 2 H+ + O2
calcitetrol + 2 oxidized adrenodoxin + H2O
-
-
-
-
?
calcitriol + 2 reduced adrenodoxin + 2 H+ + O2
calcitetrol + 2 oxidized adrenodoxin + H2O
-
-
-
-
?
calcitriol + 2 reduced adrenodoxin + 2 H+ + O2
calcitetrol + 2 oxidized adrenodoxin + H2O
-
-
-
?
calcitriol + 2 reduced adrenodoxin + 2 H+ + O2
calcitetrol + 2 oxidized adrenodoxin + H2O
-
recombinant truncated DELTA108 adrenodoxin from Bos taurus is used
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-
?
calcitriol + NADPH + H+ + O2
calcitetrol + NADP+ + H2O
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the h-P450cc24 activity is approximately 10fold higher for calcitriol than for calcidiol
-
-
?
?
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25-hydroxyvitamin D3-24-hydroxylase (CYP24A1) is a bifunctional enzyme capable of the 24-hydroxylation of 1alpha,25-dihydroxyvitamin D3, leading to the excretory form, calcitroic acid (calcitetrol), and 23-hydroxylation, culminating in 1alpha,25-dihydroxyvitamin D3-26,23-lactone
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-
?
additional information
?
-
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human CYP24A1 catalyzes both C-23 and C-24 oxidation pathways of 1alpha,25-dihydroxyvitamin D3
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-
?
additional information
?
-
calcidiol, the precursor to calcitriol, is also a substrate of CYP24A1 and is metabolized through similar pathways
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-
?
additional information
?
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CYP24A1 also catalyzes the 23-hydroxylase pathway that degrades calcidiol and calcitriol
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-
?
additional information
?
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CYP24A1 also catalyzes the 23-hydroxylase pathway that degrades calcidiol and calcitriol
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-
?
additional information
?
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enzyme activity measurements with reconstituted enzyme in phospholipid vesicles
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-
?
additional information
?
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to mediate catalysis, mitochondrial P450 enzymes, including CYP27B1 and CYP24A1, must receive electrons fromreduced nicotinamide adenine dinucleotide phosphate via ferredoxin reductase and ferredoxin. The mammalian two-hybrid assay system consisting of the retinoid-X receptor and vitamin D receptor in JEG-3 cells is used as a simple, sensitive, quantitative assay of enzyme activity
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-
?
additional information
?
-
-
to mediate catalysis, mitochondrial P450 enzymes, including CYP27B1 and CYP24A1, must receive electrons fromreduced nicotinamide adenine dinucleotide phosphate via ferredoxin reductase and ferredoxin. The mammalian two-hybrid assay system consisting of the retinoid-X receptor and vitamin D receptor in JEG-3 cells is used as a simple, sensitive, quantitative assay of enzyme activity
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-
?
additional information
?
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isolation and identification of 3-epi-calcitroic acid as the final inactive metabolite of 3-epi-1alpha,25-dihydroxyvitamin D3 produced by rat CYP24A1. Metabolite determination, overview
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-
?
additional information
?
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the precursor to calcitriol, calcidiol, is also a substrate of CYP24A1 and is metabolized through similar pathways
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-
?
additional information
?
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detailed analysis of the reversible complex between recombinant truncated enzyme DELT51CYP24A1 and recombinant truncated DELTA108adrenodoxin, kinetics, overview. Adrenodoxin binding enhances the stability of the enzyme-substrate complex, despite lowering the ligand binding affinity of the free enzyme for calcitriol over 9fold
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?