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Literature summary for 1.14.15.16 extracted from

  • Rhieu, S.Y.; Annalora, A.J.; Wang, G.; Flarakos, C.C.; Gathungu, R.M.; Vouros, P.; Sigueeiro, R.; Mourino, A.; Schuster, I.; Palmore, G.T.; Reddy, G.S.
    Metabolic stability of 3-epi-1alpha,25-dihydroxyvitamin D3 over 1alpha,25-dihydroxyvitamin D3: metabolism and molecular docking studies using rat CYP24A1 (2013), J. Cell. Biochem., 114, 2293-2305.
    View publication on PubMed

Localization

Localization Comment Organism GeneOntology No. Textmining
mitochondrion
-
Rattus norvegicus 5739
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Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
3-epi-1alpha,23,25-trihydroxy-24-oxo-vitamin D3 + 2 reduced adrenodoxin + 2 H+ + O2 Rattus norvegicus
-
3-epi-1alpha,23-dihydroxy-24,25,26,27-tetranor-vitamin D3 + 2 oxidized adrenodoxin + H2O
-
?
3-epi-1alpha,23,25-trihydroxyvitamin D3 + 2 reduced adrenodoxin + 2 H+ + O2 Rattus norvegicus
-
3-epi-1alpha,23,26-trihydroxyvitamin D3 + 2 oxidized adrenodoxin + H2O
-
?
3-epi-1alpha,23,25-trihydroxyvitamin D3 + 2 reduced adrenodoxin + 2 H+ + O2 Rattus norvegicus
-
3-epi-1alpha,25-dihydroxy-23-oxovitamin D3 + 2 oxidized adrenodoxin + H2O
-
?
3-epi-1alpha,23-dihydroxy-24,25,26,27-tetranor-vitamin D3 + 2 reduced adrenodoxin + 2 H+ + O2 Rattus norvegicus
-
3-epicalcitroic acid + 2 oxidized adrenodoxin + H2O
-
?
3-epi-1alpha,24,25-trihydroxyvitamin D3 + 2 reduced adrenodoxin + 2 H+ + O2 Rattus norvegicus
-
3-epi-1alpha,25-dihydroxy-24-oxo-vitamin D3 + 2 oxidized adrenodoxin + H2O
-
?
3-epi-1alpha,25-dihydroxy-24-oxo-vitamin D3 + 2 reduced adrenodoxin + 2 H+ + O2 Rattus norvegicus
-
3-epi-1alpha,23,25-trihydroxy-24-oxo-vitamin D3 + 2 oxidized adrenodoxin + H2O
-
?
3-epi-1alpha,25-dihydroxyvitamin D3 + 2 reduced adrenodoxin + 2 H+ + O2 Rattus norvegicus
-
3-epi-1alpha,23,25-trihydroxyvitamin D3 + 2 oxidized adrenodoxin + H2O
-
?
3-epi-1alpha,25-dihydroxyvitamin D3 + 2 reduced adrenodoxin + 2 H+ + O2 Rattus norvegicus
-
3-epi-1alpha,24,25-trihydroxyvitamin D3 + 2 oxidized adrenodoxin + H2O
-
?
3-epi-1alpha,25-dihydroxyvitamin D3 + 2 reduced adrenodoxin + 2 H+ + O2 Rattus norvegicus
-
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 Rattus norvegicus
-
3-epi-25,26,27-trinor-23,24-epoxide-1alpha-hydroxyvitamin D3 + 2 oxidized adrenodoxin + H2O
-
?
additional information Rattus norvegicus 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 ?
-
?

Organism

Organism UniProt Comment Textmining
Rattus norvegicus Q09128 gene CYP24A1
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Source Tissue

Source Tissue Comment Organism Textmining
kidney
-
Rattus norvegicus
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
3-epi-1alpha,23,25-trihydroxy-24-oxo-vitamin D3 + 2 reduced adrenodoxin + 2 H+ + O2
-
Rattus norvegicus 3-epi-1alpha,23-dihydroxy-24,25,26,27-tetranor-vitamin D3 + 2 oxidized adrenodoxin + H2O
-
?
3-epi-1alpha,23,25-trihydroxyvitamin D3 + 2 reduced adrenodoxin + 2 H+ + O2
-
Rattus norvegicus 3-epi-1alpha,23,26-trihydroxyvitamin D3 + 2 oxidized adrenodoxin + H2O
-
?
3-epi-1alpha,23,25-trihydroxyvitamin D3 + 2 reduced adrenodoxin + 2 H+ + O2
-
Rattus norvegicus 3-epi-1alpha,25-dihydroxy-23-oxovitamin D3 + 2 oxidized adrenodoxin + H2O
-
?
3-epi-1alpha,23-dihydroxy-24,25,26,27-tetranor-vitamin D3 + 2 reduced adrenodoxin + 2 H+ + O2
-
Rattus norvegicus 3-epicalcitroic acid + 2 oxidized adrenodoxin + H2O
-
?
3-epi-1alpha,24,25-trihydroxyvitamin D3 + 2 reduced adrenodoxin + 2 H+ + O2
-
Rattus norvegicus 3-epi-1alpha,25-dihydroxy-24-oxo-vitamin D3 + 2 oxidized adrenodoxin + H2O
-
?
3-epi-1alpha,25-dihydroxy-24-oxo-vitamin D3 + 2 reduced adrenodoxin + 2 H+ + O2
-
Rattus norvegicus 3-epi-1alpha,23,25-trihydroxy-24-oxo-vitamin D3 + 2 oxidized adrenodoxin + H2O
-
?
3-epi-1alpha,25-dihydroxyvitamin D3 + 2 reduced adrenodoxin + 2 H+ + O2
-
Rattus norvegicus 3-epi-1alpha,23,25-trihydroxyvitamin D3 + 2 oxidized adrenodoxin + H2O
-
?
3-epi-1alpha,25-dihydroxyvitamin D3 + 2 reduced adrenodoxin + 2 H+ + O2
-
Rattus norvegicus 3-epi-1alpha,24,25-trihydroxyvitamin D3 + 2 oxidized adrenodoxin + H2O
-
?
3-epi-1alpha,25-dihydroxyvitamin D3 + 2 reduced adrenodoxin + 2 H+ + O2
-
Rattus norvegicus 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
-
Rattus norvegicus 3-epi-25,26,27-trinor-23,24-epoxide-1alpha-hydroxyvitamin D3 + 2 oxidized adrenodoxin + H2O
-
?
additional information 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 Rattus norvegicus ?
-
?

Synonyms

Synonyms Comment Organism
CYP24A1
-
Rattus norvegicus
cytochrome P450 24A1
-
Rattus norvegicus

Cofactor

Cofactor Comment Organism Structure
adrenodoxin
-
Rattus norvegicus
heme
-
Rattus norvegicus

Expression

Organism Comment Expression
Rattus norvegicus the vitamin D receptor bound to 1alpha,25(OH)2D3 induces expression of mitochondrial cytochrome P450 24A1 up

General Information

General Information Comment Organism
metabolism CYP24A1 proceeds mainly through the C-24 oxidation pathway, resulting in its conversion into a side-chain cleaved inactive water-soluble metabolite, calcitroic acid. Isolation and identification of 3-epi-calcitroic acid as the final inactive metabolite of 3-epi-1alpha,25(OH)2D3 produced by rat CYP24A1. The amount of 3-epi-calcitroic acid produced from 3-epi-1alpha,25(OH)2D3 is threefold less than that of calcitroic acid, the analogous final inactive metabolite produced from 1alpha,25(OH)2D3, due to a slower oxidation reaction with the epimer. Molecular docking analysis using the crystal structure of rat CYP24A1 reveals that 3-epi-1alpha,25(OH)2D3, unlike 1alpha,25(OH)2D3, binds to CYP24A1 in an alternate configuration that destabilizes the formation of the enzyme-substrate complex sufficiently to slow the rate at which 3-epi-1alpha,25(OH)2D3 is inactivated by CYP24A1 through its metabolism into 3-epi-calcitroic acid. Metabolism of 1alpha,25(OH)2D3 into 3-epi-1alpha,25(OH)2D3 through the C-3 epimerization pathway, overview Rattus norvegicus
physiological function CYP24A1 is a multicatalytic enzyme that sequentially oxidizes the side chain of 1alpha,25-dihydroxyvitamin D3, leading to loss of its hormonal activity. 3-Epi-1alpha,25-dihydroxyvitamin D3 (3-epi-1alpha,25(OH)2D3), a natural metabolite of 1alpha,25-dihydroxyvitamin D3 (1alpha,25(OH)2D3), exhibits potent vitamin D receptor-mediated actions such as inhibition of keratinocyte growth or suppression of parathyroid hormone secretion Rattus norvegicus