calcipotriol   

GtoPdb Ligand ID: 2778

Synonyms: calcipotriene | Calcitrene® | Dovonex® | MC903
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.
2D Structure
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Physico-chemical Properties
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
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
Classification
Compound class Synthetic organic
Approved drug? Yes (UK (1991), FDA (1993))
IUPAC Name
(1R,3S,5Z)-5-[(2E)-2-[(1R,3aS,7aR)-1-[(E,2R,5S)-5-cyclopropyl-5-hydroxypent-3-en-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol
International Nonproprietary Names
INN number INN
6376 calcipotriol
Synonyms
calcipotriene | Calcitrene® | Dovonex® | MC903
Database Links
CAS Registry No. 112965-21-6
ChEBI CHEBI:50749
ChEMBL Ligand CHEMBL1200666
DrugBank Ligand DB02300
DrugCentral Ligand 465
GtoPdb PubChem SID 135650047
Immunopaedia Search calcipotriol
PubChem CID 5288783
RCSB PDB Ligand MC9
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SynPHARM 6446 (in complex with Vitamin D receptor)
Wikipedia Calcipotriol

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Tocris
Calcipotriol
Cat. No. 2700