Calcitroic acid

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Calcitroic acid
Calcitroic acid.svg
Names
Preferred IUPAC name
(3R)-3-[(1R,3aS,4E,7aR)-4-{(2Z)-2-[(3R,5S)-3,5-Dihydroxy-2-methylidenecyclohexylidene]ethylidene}-7a-methyloctahydro-1H-inden-1-yl]butanoic acid
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • 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
  • 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
C23H34O4
Molar mass 374.521 g·mol−1
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).[1] Often synthesized in the liver and kidneys, calcitroic acid is generated in the body after vitamin D is first converted into calcitriol, an intermediate in the fortification of bone through the formation and regulation of calcium in the body.[2] These pathways managed by calcitriol[2] are thought to be inactivated[3] through its hydroxylation by the enzyme CYP24A1, also called calcitriol 24-hydroxylase.[4] Specifically, it is thought to be the major route to inactivate vitamin D metabolites.[3]

Hydroxylation and further metabolism of calcitriol in the liver and the kidneys yields calcitroic acid,[2] a water soluble compound that is excreted in bile.[2]

A recent review suggested that current knowledge of calcitroic acid is limited, and more studies are needed to identify its physiological role.[1]

In case where a higher concentration of this acid is used in vitro, studies determined that calcitroic acid binds to vitamin D receptor (VDR) and induces gene transcription.[1]

In vivo, studies determined that calcitroic acid, along with citrulline, may be used to quantify the amount of ionizing radiation an individual has been exposed to.[5]

References[]

  1. ^ a b c Yu OB, Arnold LA (October 2016). "Calcitroic Acid-A Review". ACS Chemical Biology. 11 (10): 2665–2672. doi:10.1021/acschembio.6b00569. PMC 5074857. PMID 27574921.
  2. ^ a b c d Meyer, Daniel; Rentsch, Lara; Marti, Roger (2014). "Efficient and scalable total synthesis of calcitroic acid and its 13C-labeled derivative". RSC Adv. 4 (61): 32327–32334. Bibcode:2014RSCAd...432327M. doi:10.1039/c4ra04322g. ISSN 2046-2069.
  3. ^ a b 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.
  4. ^ Sakaki T, Kagawa N, Yamamoto K, Inouye K (January 2005). "Metabolism of vitamin D3 by cytochromes P450". Frontiers in Bioscience. 10: 119–34. doi:10.2741/1514. PMID 15574355.
  5. ^ Goudarzi, Maryam; Chauthe, Siddheshwar; Strawn, Steven J.; Weber, Waylon M.; Brenner, David J.; Fornace, Albert J. (2016-05-20). "Quantitative Metabolomic Analysis of Urinary Citrulline and Calcitroic Acid in Mice after Exposure to Various Types of Ionizing Radiation". International Journal of Molecular Sciences. 17 (5): 782. doi:10.3390/ijms17050782. ISSN 1422-0067. PMC 4881599. PMID 27213362.
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