vitamin D3   

GtoPdb Ligand ID: 2747

Synonyms: cholecalciferol
vitamin D3 is an approved drug
Comment: Vitamin D3 is one of five forms of vitamin D. It is an inactive steroid molecule with one ring open (secosteroid). Vitamin D3 is converted to bioactive calcitriol by successive hydroxylations in the liver and kidney.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 1
Hydrogen bond donors 1
Rotatable bonds 6
Topological polar surface area 20.23
Molecular weight 384.34
XLogP 9.9
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Canonical SMILES CC(CCCC(C1CCC2C1(C)CCCC2=CC=C1CC(O)CCC1=C)C)C
Isomeric SMILES CC(CCC[C@H]([C@H]1CCC2[C@]1(C)CCC/C/2=C\C=C/1\C[C@@H](O)CCC1=C)C)C
InChI InChI=1S/C27H44O/c1-19(2)8-6-9-21(4)25-15-16-26-22(10-7-17-27(25,26)5)12-13-23-18-24(28)14-11-20(23)3/h12-13,19,21,24-26,28H,3,6-11,14-18H2,1-2,4-5H3/b22-12+,23-13-/t21-,24+,25-,26?,27-/m1/s1
InChI Key QYSXJUFSXHHAJI-QWSSABAFSA-N
Classification
Compound class Metabolite or derivative
Approved drug? Yes
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
IUPAC Name
(1S,3Z)-3-[(2E)-2-[(1R,7aR)-7a-methyl-1-[(2R)-6-methylheptan-2-yl]-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexan-1-ol
Synonyms
cholecalciferol
Database Links
BindingDB Ligand 50147583
CAS Registry No. 67-97-0
ChEMBL Ligand CHEMBL432780
DrugBank Ligand DB00169
GtoPdb PubChem SID 135651594
PubChem CID 10883523
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Wikipedia Cholecalciferol