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calcifediol   Click here for help

GtoPdb Ligand ID: 6921

Synonyms: 25-hydroxyvitamin D3 | calcidiol | Calderol | Ryaldee® | U-32070E
Approved drug PDB Ligand
calcifediol is an approved drug (FDA (2016))
Compound class: Metabolite
Comment: 25-hydroxyvitamin D3 is the major circulating metabolite of 25-hydroxyvitamin D. Calcifediol is the WHO INN for the same compound.
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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 Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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 2
Hydrogen bond donors 2
Rotatable bonds 6
Topological polar surface area 40.46
Molecular weight 400.33
XLogP 7.93
No. Lipinski's rules broken 1

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES OC1CCC(=C)C(=CC=C2CCCC3(C2CCC3C(CCCC(O)(C)C)C)C)C1
Isomeric SMILES O[C@H]1CCC(=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/C27H44O2/c1-19-10-13-23(28)18-22(19)12-11-21-9-7-17-27(5)24(14-15-25(21)27)20(2)8-6-16-26(3,4)29/h11-12,20,23-25,28-29H,1,6-10,13-18H2,2-5H3/b21-11+,22-12-/t20-,23+,24-,25+,27-/m1/s1
InChI Key JWUBBDSIWDLEOM-DTOXIADCSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Metabolite
Approved drug? Yes. US FDA (2016)
IUPAC Name Click here for help
(1S,3Z)-3-[(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-methylidenecyclohexan-1-ol
International Nonproprietary Names Click here for help
INN number INN
3057 calcifediol
Synonyms Click here for help
25-hydroxyvitamin D3 | calcidiol | Calderol | Ryaldee® | U-32070E
Database Links Click here for help
CAS Registry No. 19356-17-3 (source: Scifinder)
ChEBI CHEBI:17933
ChEMBL Ligand CHEMBL1040
DrugBank Ligand DB00146
DrugCentral Ligand 464
GtoPdb PubChem SID 178103503
LIPID MAPS LMST03020246
PubChem CID 5283731
RCSB PDB Ligand VDY
Search Google for chemical match using the InChIKey JWUBBDSIWDLEOM-DTOXIADCSA-N
Search Google for chemicals with the same backbone JWUBBDSIWDLEOM
Search PubMed clinical trials calcifediol
Search PubMed titles calcifediol
Search PubMed titles/abstracts calcifediol
UniChem Compound Search for chemical match using the InChIKey JWUBBDSIWDLEOM-DTOXIADCSA-N
UniChem Connectivity Search for chemical match using the InChIKey JWUBBDSIWDLEOM-DTOXIADCSA-N
Wikipedia Calcidiol

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MedChemExpress
Calcifediol (links to external site)
Cat. No. HY-32351