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24,25-Dihydroxycholecalciferol

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24,25-Dihydroxycholecalciferol
Names
IUPAC name
(6R)-6-[(1R,3aS,4E,7aR)-4-[(2Z)-2-[(5S)-5-hydroxy-2-methylenecyclohexylidene]ethylidene]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-1-yl]-2-methylheptane-2,3-diol
Other names
24,25-dihydroxyvitamin D3
(24R)-hydroxycalcifediol
(24R)-hydroxycalcidiol
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.049.754 Edit this at Wikidata
UNII
  • InChI=1S/C27H44O3/c1-18-8-12-22(28)17-21(18)11-10-20-7-6-16-27(5)23(13-14-24(20)27)19(2)9-15-25(29)26(3,4)30/h10-11,19,22-25,28-30H,1,6-9,12-17H2,2-5H3/b20-10+,21-11-/t19-,22+,23-,24+,25?,27-/m1/s1 checkY
    Key: FCKJYANJHNLEEP-SRLFHJKTSA-N checkY
  • InChI=1/C27H44O3/c1-18-8-12-22(28)17-21(18)11-10-20-7-6-16-27(5)23(13-14-24(20)27)19(2)9-15-25(29)26(3,4)30/h10-11,19,22-25,28-30H,1,6-9,12-17H2,2-5H3/b20-10+,21-11-/t19-,22+,23-,24+,25?,27-/m1/s1
    Key: FCKJYANJHNLEEP-SRLFHJKTBM
  • O[C@@H]1CC(\C(=C)CC1)=C\C=C2/CCC[C@]3([C@H]2CC[C@@H]3[C@H](C)CCC(O)C(O)(C)C)C
Properties
C27H44O3
Molar mass 416.63 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

24,25-Dihydroxycholecalciferol, also known as 24,25-dihydroxyvitamin D3 and (24R)-hydroxycalcidiol (abbreviated as 24(R),25-(OH)2D3),[1] is a compound which is closely related to 1,25-dihydroxyvitamin D3, the active form of vitamin D3. Like vitamin D3 itself and calcifediol (25-hydroxyvitamin D3), it is inactive as a hormone both in vitro[2] and in vivo.[3] It was first identified in 1972 in the laboratory of Hector DeLuca and Michael F. Holick.[4]

Formation and significance

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24,25-dihydroxyvitamin D3 is formed from 25-hydroxyvitamin D3 by the action of CYP24A1 (25-hydroxyvitamin D3-24-hydroxylase). CYP24A1 appears to be "a multicatalytic enzyme catalyzing most, if not all, of the reactions in the C-24/C-23 pathway of 25-OH-D3 metabolism."[5]

It has been proposed that 24,25-dihydroxyvitamin D3 is a metabolite of 25-hydroxyvitamin D3 which is destined for excretion.[5]

It is not known whether the compound might also have some physiologically significant activity. Some evidence of a possible receptor has been obtained.[6]

Because 24,25-dihydroxycholecalciferol is considered an inactive metabolite and its significance is that its concentration is expected to decrease in case of mutations inactivating the vitamin D 24-hydroxylase gene.

Interactive pathway map

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Click on genes, proteins and metabolites below to link to respective articles. [§ 1]

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VitaminDSynthesis_WP1531Go to articleGo to articleGo to articleGo to articlego to articleGo to articleGo to articleGo to articlego to articlego to articlego to articlego to articleGo to articleGo to articlego to articleGo to articlego to articlego to articlego to articleGo to articlego to article
|alt=Vitamin D Synthesis Pathway (view / edit)]]
Vitamin D Synthesis Pathway (view / edit)
  1. ^ The interactive pathway map can be edited at WikiPathways: "VitaminDSynthesis_WP1531".

References

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  1. ^ "IUPAC-IUB Joint Commission on Biochemical Nomenclature (JCBN): Nomenclature of vitamin D. Recommendations 1981". European Journal of Biochemistry. 124 (2): 223–7. May 1982. doi:10.1111/j.1432-1033.1982.tb06581.x. PMID 7094913.
  2. ^ Sørnes S, Bjøro T, Berg JP, Torjesen PA, Haug E (May 1994). "Calcitriol attenuates the basal and vasoactive intestinal peptide-stimulated cAMP production in prolactin-secreting rat pituitary (GH4C1) cells". Mol Cell Endocrinol. 101 (1–2): 183–8. doi:10.1016/0303-7207(94)90233-x. PMID 9397951. S2CID 42457340.
  3. ^ Mortensen BM, Gautvik KM, Gordeladze JO (February 1993). "Bone turnover in rats treated with 1,25-dihydroxyvitamin D3, 25-hydroxyvitamin D3 or 24,25-dihydroxyvitamin D3". Biosci Rep. 13 (1): 27–39. doi:10.1007/BF01138176. PMID 8392394. S2CID 19689388.
  4. ^ Holick, MF; Schnoes, HK; Deluca, HF; Gray, RW; Boyle, IT; Suda, T (1972). "Isolation and identification of 24,25-dihydroxycholecalciferol, a metabolite of vitamin D made in the kidney". Biochemistry. 11 (23): 4251–5. doi:10.1021/bi00773a009. PMID 4342902.
  5. ^ a b Beckman MJ, Tadikonda P, Werner E, Prahl J, Yamada S, DeLuca HF (June 1996). "Human 25-hydroxyvitamin D3-24-hydroxylase, a multicatalytic enzyme". Biochemistry. 35 (25): 8465–72. doi:10.1021/bi960658i. PMID 8679605.
  6. ^ Sömjen D, Sömjen GJ, Weisman Y, Binderman I (April 1982). "Evidence for 24,25-dihydroxycholecalciferol receptors in long bones of newborn rats". Biochem J. 204 (1): 31–6. doi:10.1042/bj2040031. PMC 1158312. PMID 6981414.
[edit]
  • Mata-Granados, J. M.; Luque De Castro, M. D.; Quesada Gomez, J. M. (2008). "Inappropriate serum levels of retinol, α-tocopherol, 25 hydroxyvitamin D3 and 24,25 dihydroxyvitamin D3 levels in healthy Spanish adults: Simultaneous assessment by HPLC". Clinical Biochemistry. 41 (9): 676–680. doi:10.1016/j.clinbiochem.2008.02.003. PMID 18313404.