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
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (UK (1991), FDA (1993))
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
IUPAC Name Click here for help
(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 Click here for help
INN number INN
6376 calcipotriol
Synonyms Click here for help
calcipotriene | Calcitrene® | Dovonex® | MC903
Database Links Click here for help
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
LIPID MAPS LMST03020106
PubChem CID 5288783
RCSB PDB Ligand MC9
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SynPHARM 6446 (in complex with Vitamin D receptor)
UniChem Compound Search for chemical match using the InChIKey LWQQLNNNIPYSNX-UROSTWAQSA-N
UniChem Connectivity Search for chemical match using the InChIKey LWQQLNNNIPYSNX-UROSTWAQSA-N
Wikipedia Calcipotriol

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Tocris
Calcipotriol (links to external site)
Cat. No. 2700