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
3D model of 1alpha,25-dihydroxy-2beta-(3-hydroxypropoxy)vitamin D3
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Category
Main Class
Sub Class
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
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
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
Admin
Created at
-
Updated at
17th Feb 2022