24,25-Dihydroxycholecalciferol

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, but like vitamin D₃ itself and 25-hydroxyvitamin D₃ is inactive as a hormone both in vitro[2] and in vivo.[3] It was identified by Michael F. Holick.[4]

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
CAS Number	40013-87-4^Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL47183^Y
ChemSpider	4939193^Y
ECHA InfoCard	100.049.754
PubChem CID	6434253
UNII	0AXX2V8L5Z^Y
InChI 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^Y Key: FCKJYANJHNLEEP-SRLFHJKTSA-N^Y 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
SMILES 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
Chemical formula	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).
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Infobox references

Formation and significance

24,25-dihydroxyvitamin D₃ is formed from 25-hydroxyvitamin D₃ by the action of P450cc24 (25-hydroxyvitamin D3-24-hydroxylase), which 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]

Interactive pathway map

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

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|{{{bSize}}}px|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

1. "Nomenclature of Vitamin D. Recommendations 1981. IUPAC-IUB Joint Commission on Biochemical Nomenclature (JCBN) Archived 2017-08-23 at the Wayback Machine" reproduced at the Queen Mary, University of London website. Retrieved 21 March 2010.
2. Sørnes, S.; Bjøro, T.; Berg, J. P.; Torjesen, P. A.; Haug, E. (1994). "Calcitriol attenuates the basal and vasoactive intestinal peptide-stimulated cAMP production in prolactin-secreting rat pituitary (GH4C1) cells". Molecular and Cellular Endocrinology. 101 (1–2): 183–188. doi:10.1016/0303-7207(94)90233-x. PMID 9397951.
3. Mortensen, B. M.; Gautvik, K. M.; Gordeladze, J. O. (1993). "Bone turnover in rats treated with 1,25-dihydroxyvitamin D3, 25-hydroxyvitamin D3 or 24,25-dihydroxyvitamin D3". Bioscience Reports. 13 (1): 27–39. doi:10.1007/bf01138176. PMID 8392394.
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. Beckman, M. J.; Tadikonda, P.; Werner, E.; Prahl, J.; Yamada, S.; Deluca, H. F. (1996). "Human 25-Hydroxyvitamin D3-24-Hydroxylase, a Multicatalytic Enzyme†". Biochemistry. 35 (25): 8465–8472. doi:10.1021/bi960658i. PMID 8679605.
6. Sömjen, D.; Sömjen, G. J.; Weisman, Y.; Binderman, I. (1982). "Evidence for 24,25-dihydroxycholecalciferol receptors in long bones of newborn rats". The Biochemical Journal. 204 (1): 31–36. doi:10.1042/bj2040031. PMC 1158312. PMID 6981414.

Other articles

• 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.