calcipotriol   Click here for help

GtoPdb Ligand ID: 2778

Synonyms: calcipotriene | Calcitrene® | Dovonex® | MC903
Approved drug PDB Ligand
calcipotriol is an approved drug (UK (1991), FDA (1993))
Compound class: Synthetic organic
Comment: Calcipotriol is a synthetic analogue of vitamin D, and acts as an agonist at the vitamin D receptor.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 3
Rotatable bonds 5
Topological polar surface area 60.69
Molecular weight 412.3
XLogP 5.82
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES OC1CC(O)C(=C)C(=CC=C2CCCC3(C2CCC3C(C=CC(C2CC2)O)C)C)C1
Isomeric SMILES O[C@H]1C[C@H](O)C(=C)/C(=C\C=C\2/CCC[C@]3([C@H]2CC[C@@H]3[C@@H](/C=C/[C@H](C2CC2)O)C)C)/C1
InChI InChI=1S/C27H40O3/c1-17(6-13-25(29)20-8-9-20)23-11-12-24-19(5-4-14-27(23,24)3)7-10-21-15-22(28)16-26(30)18(21)2/h6-7,10,13,17,20,22-26,28-30H,2,4-5,8-9,11-12,14-16H2,1,3H3/b13-6+,19-7+,21-10-/t17-,22-,23-,24+,25-,26+,27-/m1/s1
InChI Key LWQQLNNNIPYSNX-UROSTWAQSA-N
References
1. Bishop JE, Collins ED, Okamura WH, Norman AW. (1994)
Profile of ligand specificity of the vitamin D binding protein for 1 alpha,25-dihydroxyvitamin D3 and its analogs.
J Bone Miner Res, 9 (8): 1277-88. [PMID:7976510]