Calcitroic acid (D3)

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[edit] Description

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Calcitroic acid (1 alpha-hydroxy-23 carboxy-24,25,26,27-tetranorvitamin D(3)) is a metabolite of 1 alpha, 25-dihydroxyvitamin D(3) (calcitriol). It is soluble in water, and is excreted in urine. This deactivation process involves a series of oxidation reactions at C24 and C23 leading to side-chain cleavage and, ultimately, formation of the calcitroic acid. This deactivation involves the loss of carbons 24, 25, 26, and 27 and the oxidation of carbon 23 to a carboxylic acid. Calcitroic acid is also a major terminal product for the deactivation of 1α,25-dihydroxyvitamin D2. Both the kidney and the intestine metabolize 1,25-dihydroxyvitamin D3 through the C-24 oxidation pathway according to the following steps: 1,25-dihydroxyvitamin D3----1,24,25-trihydroxyvitamin D3----1,25-dihydroxy-24-oxovitamin D3-----1,23,25-trihydroxy-24-oxovitamin D3 (PMID: 2719932). The C-24 oxidation pathway leading to the formation of calcitroic acid has been reported to be present in bone cells, but the C-23 oxidation pathway leading to the formation of 1 alpha, 25-(OH)2D3-26,23-lactone has not been described in bone cells, even though 1 alpha, 25-(OH)2D3-26,23-lactone is noted to have a significant effect on bone formation. (PMID: 7664636)

[edit] General Properties

*Molecular Weight

374.51

*Molecular Formula

C₂₃H₃₄O₄

*IUPAC NAME

1,3-dihydroxy-(1a,3b,5Z,7E)-24-nor-9,10-secochola-5,7,10(19)-trien-23-oic acid

*Canonical Smiles

CC(CC(O)=O)C1CCC2C(CCCC12C)=CC=C1CC(O)CC(O)C1=C

*Isomeric Smiles

C[C@H](CC(O)=O)[C@H]1CC[C@H]2C(CCC[C@]12C)=CC=C1/C[C@@H](O)C[C@H](O)C1=C

[edit] PhysioChemical Properties

*Melting Point

*LogP

*Water Solubility

[edit] External Links

• [1]Human Metabolome DataBase