Calcitroic acid

Calcitroic acid
Names
	IUPAC name (3R)-3-[(1R,3aR,4E,7aR)- 4-[(2Z)-2-[(3R,5R)-3,5- Dihydroxy-2-methylene-cyclohexylidene]ethylidene] -7a-methyl-2,3,3a,5,6,7-hexahydro-1H -inden-1-yl]butanoic acid
Identifiers
CAS Number	71204-89-2;
3D model (JSmol)	Interactive image;
ChemSpider	4947800;
PubChem CID	6443842;
	InChI InChI=1/C23H34O4/c1-14(11-22(26)27)19-8-9-20-16(5-4-10-23(19,20)3)6-7-17-12-18(24)13-21(25)15(17)2/h6-7,14,18-21,24-25H,2,4-5,8-13H2,1,3H3,(H,26,27)/b16-6+,17-7-/t14-,18+,19-,20+,21-,23-/m1/s1 Key: MBLYZRMZFUWLOZ-FEUSBDLHBT;
	SMILES O=C(O)C[C@@H](C)[C@H]3CC[C@H]2C(=C\C=C1/C(=C)[C@H](O)C[C@@H](O)C1)\CCC[C@@]23C;
Properties
Chemical formula	C23H34O4
Molar mass	374.514
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

Calcitroic acid (1α-hydroxy-23-carboxy-24,25,26,27-tetranorvitamin D₃) is a major metabolite of 1α,25-dihydroxyvitamin D₃ (calcitriol). Its formation is catalyzed by the enzyme CYP24A1, also called calcitriol 24-hydroxylase.^[1] It is thought to be the major route to inactivate vitamin D metabolites.^[2] Calcitroic acid is soluble in water and excreted in bile.

A recent review suggested that current knowledge of calcitroic acid is limited, and more studies are needed to identify its physiological role.^[3]

References

↑ Sakaki T, Kagawa N, Yamamoto K, Inouye K (January 2005). "Metabolism of vitamin D₃ by cytochromes P450". Front. Biosci. 10: 119–34. doi:10.2741/1514. PMID 15574355.
↑ Jones, G; Prosser, DE; Kaufmann, M (January 2014). "Cytochrome P450-mediated metabolism of vitamin D." Journal of Lipid Research. 55 (1): 13–31. doi:10.1194/jlr.R031534. PMC 3927478. PMID 23564710.
↑ Yu, OB; Arnold, LA (21 October 2016). "Calcitroic Acid-A Review". ACS chemical biology. 11 (10): 2665–2672. doi:10.1021/acschembio.6b00569. PMC 5074857. PMID 27574921.

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[pmid15574355-1] Sakaki T, Kagawa N, Yamamoto K, Inouye K (January 2005). "Metabolism of vitamin D₃ by cytochromes P450". Front. Biosci. 10: 119–34. doi:10.2741/1514. PMID 15574355.

[2] Jones, G; Prosser, DE; Kaufmann, M (January 2014). "Cytochrome P450-mediated metabolism of vitamin D." Journal of Lipid Research. 55 (1): 13–31. doi:10.1194/jlr.R031534. PMC 3927478. PMID 23564710.

[3] Yu, OB; Arnold, LA (21 October 2016). "Calcitroic Acid-A Review". ACS chemical biology. 11 (10): 2665–2672. doi:10.1021/acschembio.6b00569. PMC 5074857. PMID 27574921.

Names

IUPAC name (3R)-3-[(1R,3aR,4E,7aR)- 4-[(2Z)-2-[(3R,5R)-3,5- Dihydroxy-2-methylene-cyclohexylidene]ethylidene] -7a-methyl-2,3,3a,5,6,7-hexahydro-1H -inden-1-yl]butanoic acid
Identifiers
CAS Number	71204-89-2
3D model (JSmol)	Interactive image
ChemSpider	4947800
PubChem CID	6443842
InChI InChI=1/C23H34O4/c1-14(11-22(26)27)19-8-9-20-16(5-4-10-23(19,20)3)6-7-17-12-18(24)13-21(25)15(17)2/h6-7,14,18-21,24-25H,2,4-5,8-13H2,1,3H3,(H,26,27)/b16-6+,17-7-/t14-,18+,19-,20+,21-,23-/m1/s1 Key: MBLYZRMZFUWLOZ-FEUSBDLHBT
SMILES O=C(O)C[C@@H](C)[C@H]3CC[C@H]2C(=C\C=C1/C(=C)[C@H](O)C[C@@H](O)C1)\CCC[C@@]23C
Properties
Chemical formula	C₂₃H₃₄O₄
Molar mass	374.514
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references