calcitriol-26,23-lactone   

GtoPdb Ligand ID: 2786

Synonyms: (23S,25R)-1α,25-(OH)2D3-26,23-lactone | 1,25-dihydroxyvitamin D3-26,23-lactone | 1,25-lactone
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 5
Hydrogen bond donors 3
Rotatable bonds 4
Topological polar surface area 86.99
Molecular weight 444.29
XLogP 5.26
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Canonical SMILES OC1CC(O)C(=C)C(=CC=C2CCCC3(C2CCC3C(CC2OC(=O)C(C2)(C)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@@H]2OC(=O)[C@](C2)(C)O)C)C)/C1
InChI InChI=1S/C27H40O5/c1-16(12-21-15-27(4,31)25(30)32-21)22-9-10-23-18(6-5-11-26(22,23)3)7-8-19-13-20(28)14-24(29)17(19)2/h7-8,16,20-24,28-29,31H,2,5-6,9-15H2,1,3-4H3/b18-7+,19-8-/t16-,20-,21+,22-,23+,24+,26-,27-/m1/s1
InChI Key WMYIVSWWSRCZFA-RWVJFQLJSA-N
References
1. Shiina Y, Abe E, Miyaura C, Tanaka H, Yamada S, Ohmori M, Nakayama K, Takayama H, Matsunaga I, Nishii Y, DeLuca HF, Suda T. (1983)
Biological activity of 24,24-difluoro-1 alpha, 25-dihydroxyvitamin D3 and 1 alpha, 25-dihydroxyvitamin D3-26,23-lactone in inducing differentiation of human myeloid leukemia cells.
Arch. Biochem. Biophys., 220 (1): 90-4. [PMID:6572492]