1,25-dihydroxyvitamin D3   Click here for help

GtoPdb Ligand ID: 2779

Synonyms: Calcijex® | calcitriol | Rocaltrol®
Approved drug PDB Ligand
1,25-dihydroxyvitamin D3 is an approved drug (FDA (1978))
Compound class: Metabolite
Comment: Vitamin D receptor agonist. Calcitrol is the active form of vitamin D found in the body.
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

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View more information in the IUPHAR Pharmacology Education Project: calcitrol

1,25-dihydroxyvitamin D3 is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 3
Hydrogen bond donors 3
Rotatable bonds 6
Topological polar surface area 60.69
Molecular weight 416.33
XLogP 6.75
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES OC1CC(O)C(=C)C(=CC=C2CCCC3(C2CCC3C(CCCC(O)(C)C)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](CCCC(O)(C)C)C)C)/C1
InChI InChI=1S/C27H44O3/c1-18(8-6-14-26(3,4)30)23-12-13-24-20(9-7-15-27(23,24)5)10-11-21-16-22(28)17-25(29)19(21)2/h10-11,18,22-25,28-30H,2,6-9,12-17H2,1,3-5H3/b20-10+,21-11-/t18-,22-,23-,24+,25+,27-/m1/s1
InChI Key GMRQFYUYWCNGIN-NKMMMXOESA-N
Classification Click here for help
Compound class Metabolite
Approved drug? Yes (FDA (1978))
IUPAC Name Click here for help
(1R,3S,5Z)-5-[(2E)-2-[(1R,3aS,7aR)-1-[(2R)-6-hydroxy-6-methylheptan-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
4393 calcitriol
Synonyms Click here for help
Calcijex® | calcitriol | Rocaltrol®
Database Links Click here for help
CAS Registry No. 32222-06-3
ChEBI CHEBI:17823
ChEMBL Ligand CHEMBL846
DrugBank Ligand DB00136
DrugCentral Ligand 466
GtoPdb PubChem SID 135651370
LIPID MAPS LMST03020258
PubChem CID 5280453
RCSB PDB Ligand VDX
Search Google for chemical match using the InChIKey GMRQFYUYWCNGIN-NKMMMXOESA-N
Search Google for chemicals with the same backbone GMRQFYUYWCNGIN
Search PubMed clinical trials calcitriol
Search PubMed titles calcitriol
Search PubMed titles/abstracts calcitriol
SynPHARM 6450 (in complex with Vitamin D receptor)
UniChem Compound Search for chemical match using the InChIKey GMRQFYUYWCNGIN-NKMMMXOESA-N
UniChem Connectivity Search for chemical match using the InChIKey GMRQFYUYWCNGIN-NKMMMXOESA-N
Wikipedia Calcitriol

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Tocris
Calcitriol (links to external site)
Cat. No. 2551