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Structure Database (LMSD)

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Common Name

1alpha,25-dihydroxyvitamin D3

Systematic Name

(5Z,7E)-(1S,3R)-9,10-seco-5,7,10(19)-cholestatriene-1,3,25-triol

Synonyms

1alpha,25-dihydroxycholecalciferol
calcitriol

LM ID

LMST03020258

Formula

C₂₇H₄₄O₃

Exact Mass

Calculate m/z

416.329046

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

Calcitriol is a vitamin D3 receptor agonist and active metabolite of vitamin D3 .^1,2 It is formed via a multi-step process, in which vitamin D3 undergoes hydroxylation to 25-hydroxy vitamin D3 in the liver, followed by further hydroxylation at the 1α-position in the kidney. Calcitriol binds to the vitamin D3 receptor (Kd = 16 pM) and induces differentiation of U937 acute monocytic leukemia cells (EC50 = 2,000 pM).³ It induces cell cycle arrest at the S phase and apoptosis in primary adenomatous and hyperplastic human parathyroid cells when used at a concentration of 10 nM.⁴ Calcitriol (0.65 nmol/animal) increases bone calcium mobilization in chicks on a low calcium diet.² It stimulates calcium absorption in the intestines in a chick model of rickets induced by a vitamin D3-deficient diet when administered at a dose of 25 µg/animal.¹ Formulations containing calcitriol have been used in the treatment of hypocalcemia.

This information has been provided by Cayman Chemical

References

1. Canalejo, A., Almadén, Y., Torregrosa, V., et al. The in vitro effect of calcitriol on parathyroid cell proliferation and apoptosis. J. Am. Soc. Nephrol. 11(10), 1865-1872 (2000).

2. Haussler, M.R., Zerwekh, J.E., Hesse, R.H., et al. Biological activity of 1α-hydroxycholecalciferol, a synthetic analog of the hormonal form of vitamin D3. Proc. Natl. Acad. Sci. USA 70(8), 2248-2252 (1973).

3. Lawson, D.E., Fraser, D.R., Kodicek, E., et al. Identification of 1,25-dihydroxycholecalciferol, a new kidney hormone controlling calcium metabolism. Nature 230(5291), 228-230 (1971).

4. Binderup, L., Latini, S., Binderup, E., et al. 20-epi-vitamin D3 analogues: A novel class of potent regulators of cell growth and immune responses. Biochem. Pharmacol. 42(8), 1569-1575 (1991).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Gallus gallus (#9031)

Aves (#8782)

The synthesis of 1α,25-dihydroxycholecalciferol -- A metabolically active form of vitamin D3,
Tetrahedron Letts, 1972

DOI: 10.1016/S0040-4039(01)94260-1

String Representations

InChiKey (Click to copy)

GMRQFYUYWCNGIN-NKMMMXOESA-N

InChi (Click to copy)

InChI=1S/C27H44O3/c1-18(8-6-14-26(3,4)30)23-12-13-24-20(9-7-15-27(23,24)5)10-11-21-16-22(28)17-25(29)19(21)2/h10-11,18,22-25,28-30H,2,6-9,12-17H2,1,3-5H3/b20-10+,21-11-/t18-,22-,23-,24+,25+,27-/m1/s1

SMILES (Click to copy)

[C@@H]1(O)C(=C)/C(=C\C=C2\[C@]3([H])CC[C@@]([H])([C@@]3(C)CCC\2)[C@]([H])(C)CCCC(O)(C)C)/C[C@@H](O)C1