corticosterone   Click here for help

GtoPdb Ligand ID: 2869

PDB Ligand Immunopharmacology Ligand
Compound class: Metabolite
Comment: Endogenous glucocorticoid.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 2
Rotatable bonds 2
Topological polar surface area 74.6
Molecular weight 346.21
XLogP 1.7
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES OCC(=O)C1CCC2C1(C)CC(O)C1C2CCC2=CC(=O)CCC12C
Isomeric SMILES OCC(=O)[C@H]1CC[C@@H]2[C@]1(C)C[C@H](O)[C@H]1[C@H]2CCC2=CC(=O)CC[C@]12C
InChI InChI=1S/C21H30O4/c1-20-8-7-13(23)9-12(20)3-4-14-15-5-6-16(18(25)11-22)21(15,2)10-17(24)19(14)20/h9,14-17,19,22,24H,3-8,10-11H2,1-2H3/t14-,15-,16+,17-,19+,20-,21-/m0/s1
InChI Key OMFXVFTZEKFJBZ-HJTSIMOOSA-N
References
1. Hellal-Levy C, Couette B, Fagart J, Souque A, Gomez-Sanchez C, Rafestin-Oblin M. (1999)
Specific hydroxylations determine selective corticosteroid recognition by human glucocorticoid and mineralocorticoid receptors.
FEBS Lett, 464 (1-2): 9-13. [PMID:10611474]
2. Lind U, Greenidge P, Gillner M, Koehler KF, Wright A, Carlstedt-Duke J. (2000)
Functional probing of the human glucocorticoid receptor steroid-interacting surface by site-directed mutagenesis. Gln-642 plays an important role in steroid recognition and binding.
J Biol Chem, 275 (25): 19041-9. [PMID:10747884]
3. Rupprecht R, Reul JM, van Steensel B, Spengler D, Söder M, Berning B, Holsboer F, Damm K. (1993)
Pharmacological and functional characterization of human mineralocorticoid and glucocorticoid receptor ligands.
Eur J Pharmacol, 247 (2): 145-54. [PMID:8282004]