doxercalciferol   

GtoPdb Ligand ID: 2790

Synonyms: 1α-hydroxyvitamin D2 | 1αOHD2  | 1-α-hydroxyergocalciferol
doxercalciferol is an approved drug (FDA (2000))
Comment: Doxercalciferol is a synthetic analogue of vitamin D2 (ergocalciferol).
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 2
Hydrogen bond donors 2
Rotatable bonds 5
Topological polar surface area 40.46
Molecular weight 412.33
XLogP 8.69
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Canonical SMILES OC1CC(O)C(=C)C(=CC=C2CCCC3(C2CCC3C(C=CC(C(C)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](/C=C/[C@@H](C(C)C)C)C)C)/C1
InChI InChI=1S/C28H44O2/c1-18(2)19(3)9-10-20(4)25-13-14-26-22(8-7-15-28(25,26)6)11-12-23-16-24(29)17-27(30)21(23)5/h9-12,18-20,24-27,29-30H,5,7-8,13-17H2,1-4,6H3/b10-9+,22-11+,23-12-/t19-,20+,24+,25+,26-,27-,28+/m0/s1
InChI Key HKXBNHCUPKIYDM-CGMHZMFXSA-N
Classification
Compound class Metabolite or derivative
Approved drug? Yes (FDA (2000))
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
IUPAC Name
(1R,3S,5Z)-5-[(2E)-2-[(1R,3aS,7aR)-1-[(E,2R,5R)-5,6-dimethylhept-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
7878 doxercalciferol
Synonyms
1α-hydroxyvitamin D2 | 1αOHD2  | 1-α-hydroxyergocalciferol
Database Links
CAS Registry No. 54573-75-0 (source: Scifinder)
ChEBI CHEBI:4712
ChEMBL Ligand CHEMBL1200810
DrugCentral Ligand 957
GtoPdb PubChem SID 135651481
PubChem CID 5281107
RCSB PDB Ligand V2H
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Wikipedia Doxercalciferol

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Tocris
Doxercalciferol
Cat. No. 3206