Structure Database (LMSD)
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
3D model of 19-Nor-14-epi-23-yne-1,25 dihydroxyvitamin 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
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
References
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
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
29
Rings
3
Aromatic Rings
0
Rotatable Bonds
3
Van der Waals Molecular Volume
437.09
Topological Polar Surface Area
60.69
Hydrogen Bond Donors
3
Hydrogen Bond Acceptors
3
logP
5.62
Molar Refractivity
119.59
Admin
Created at
-
Updated at
13th Jun 2021