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Structure Database (LMSD)

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Common Name

19-Nor-14-epi-23-yne-1,25 dihydroxyvitamin D3

Systematic Name

(7E)-(1R,3R,14R)-19-nor-23-yne-9,10-seco-5,7-cholestadiene-1,3,25-triol

Synonyms

TX 522
Inecalcitol

LM ID

LMST03020649

Formula

C₂₆H₄₀O₃

Exact Mass

Calculate m/z

400.297745

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

Inecalcitol is a derivative of calcitriol and an agonist of the vitamin D receptor (VDR).¹ It induces reporter gene expression in VDR-expressing COS-1 cells when used at a concentration of 1 nM. Inecalcitol induces differentiation of HL-60 leukemia and MG-63 osteosarcoma cells (EC50s = 6.2 and 0.18 nM, respectively) and reduces the proliferation of MCF-7 breast cancer cells (EC50 = 4.1 nM).² It protects primary human keratinocytes against DNA damage induced by UVB irradiation in a concentration-dependent manner.³ Inecalcitol (100 nM) inhibits acetylcholine- or ATP-induced contractions of aortic rings isolated from spontaneously hypertensive rats.⁴ Unlike calcitriol, inecalcitol (80 µg/kg) does not increase serum calcium levels or decrease tibia calcium levels in mice.²

This information has been provided by Cayman Chemical

References

1. Wong, M.S.K., Delansorne, R., Man, R.Y.K., et al. Vitamin D derivatives acutely reduce endothelium-dependent contractions in the aorta of the spontaneously hypertensive rat. Am. J. Physiol. Heart Circ. Physiol. 295(1), H289-H296 (2008).

2. De Haes, P., Garmyn, M., Verstuyf, A., et al. 1,25-Dihydroxyvitamin D3 and analogues protect primary human keratinocytes against UVB-induced DNA damage. J. Photochem. Photobiol. B 78(2), 141-148 (2005).

3. Verlinden, L., Verstuyf, A., Van Camp, M., et al. Two novel 14-epi-analogues of 1,25-dihydroxyvitamin D3 inhibit the growth of human breast cancer cells in vitro and in vivo. Cancer Res. 60(10), 2673-2679 (2000).

4. Eelen, G., Verlinden, L., Rochel, N., et al. Superagonistic action of 14-epi-analogs of 1,25-dihydroxyvitamin D explained by vitamin D receptor-coactivator interaction. Mol. Pharmacol. 67(5), 1566-1573 (2005).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

synthetic construct (#32630)

Two novel 14-Epi-analogues of 1,25-dihydroxyvitamin D3 inhibit the growth of human breast cancer cells in vitro and in vivo.,
Cancer Res, 2000

Pubmed ID: 10825140

String Representations

InChiKey (Click to copy)

HHGRMHMXKPQNGF-WNSNRMDMSA-N

InChi (Click to copy)

InChI=1S/C26H40O3/c1-18(7-5-13-25(2,3)29)23-11-12-24-20(8-6-14-26(23,24)4)10-9-19-15-21(27)17-22(28)16-19/h9-10,18,21-24,27-29H,6-8,11-12,14-17H2,1-4H3/b20-10+/t18-,21-,22-,23-,24-,26-/m1/s1

SMILES (Click to copy)

C1/C(=C/C=C2\CCC[C@]3(C)[C@@]([H])([C@]([H])(C)CC#CC(O)(C)C)CC[C@]\23[H])/C[C@@H](O)C[C@@H]1O