Structure Database (LMSD)

Common Name
1alpha,25-dihydroxy-2beta-(3-hydroxypropoxy)vitamin D3
Systematic Name
(5Z,7E)-(1R,2R,3R)-2-(3-hydroxypropoxy)-9,10-seco-5,7,10(19)-cholestatriene-1,3,25-triol
Synonyms
  • 1alpha,25-dihydroxy-2beta-(3-hydroxypropoxy)cholecalciferol
LM ID
LMST03020477
Formula
Exact Mass
Calculate m/z
490.365826
Status
Curated

Classification

Biological Context

Eldecalcitol is a derivative of the vitamin D3 receptor agonist and vitamin D3 active metabolite calcitriol .1,2 It induces calcium release in an in vitro bone mobilization assay using isolated mouse calvaria when used at a concentration of 10 nM.1 Eldecalcitol (50 nM) reduces LPS-induced pyroptosis and increases in hydrogen peroxide and protein levels of the NOD-like receptor protein 3 (NLRP3) inflammasome, caspase-1, and IL-1β in primary human gingival fibroblasts.3 Eldecalcitol (0.4 nM) induces apoptosis and cell cycle arrest at the G0/G1 phase in, and inhibits migration of, SCC-15 and CAL 27 squamous cell carcinoma cells and decreases tumor volume in an SCC-15 mouse xenograft model when administered at a dose of 0.5 µg/kg twice per week.4 Eldecalcitol (0.3 µg/kg) decreases serum parathyroid hormone (PTH) levels and increases serum calcium levels, bone mineral density, and bone strength in a cynomolgus monkey model of osteoporosis induced by ovariectomy.2 Formulations containing eldecalcitol have been used in the treatment of osteoporosis.

This information has been provided by Cayman Chemical

References

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
synthetic construct (#32630)
Synthetic studies of vitamin D analogs. XXIV. Synthesis of active vitamin D3 analogs substituted at the 2 beta-position and their preventive effects on bone mineral loss in ovariectomized rats.,
Chem Pharm Bull (Tokyo), 1997
Pubmed ID: 9353890

String Representations

InChiKey (Click to copy)
FZEXGDDBXLBRTD-AYIMTCTASA-N
InChi (Click to copy)
InChI=1S/C30H50O5/c1-20(9-6-15-29(3,4)34)24-13-14-25-22(10-7-16-30(24,25)5)11-12-23-19-26(32)28(27(33)21(23)2)35-18-8-17-31/h11-12,20,24-28,31-34H,2,6-10,13-19H2,1,3-5H3/b22-11+,23-12-/t20-,24-,25+,26-,27-,28-,30-/m1/s1
SMILES (Click to copy)
[C@@H]1(O)C(=C)/C(=C\C=C2\[C@]3([H])CC[C@@]([C@@](C)([H])CCCC(O)(C)C)([H])[C@@]3(C)CCC\2)/C[C@@H](O)[C@H]1OCCCO

Other Databases

CHEBI ID
LIPIDBANK ID
VVD0567
PubChem CID
Cayman ID
PDB ID
GuidePharm ID

Calculated Physicochemical Properties

Heavy Atoms 35
Rings 3
Aromatic Rings 0
Rotatable Bonds 10
Van der Waals Molecular Volume 526.51
Topological Polar Surface Area 90.15
Hydrogen Bond Donors 4
Hydrogen Bond Acceptors 5
logP 6.80
Molar Refractivity 143.89

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Created at
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Updated at
17th Feb 2022