(-)-propranolol   Click here for help

GtoPdb Ligand ID: 63

PDB Ligand
Compound class: Synthetic organic
Comment: A component of the approved drug propranolol. Propranolol is a racemic mixture of two enantiomers (+)-propranolol, and (-)-propranolol. Some of the database entries linked to from this page may refer to the mixture and do not specify stereochemistry in the images of the structue shown.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 2
Hydrogen bond donors 2
Rotatable bonds 6
Topological polar surface area 41.49
Molecular weight 259.16
XLogP 3.03
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES OC(COc1cccc2c1cccc2)CNC(C)C
Isomeric SMILES O[C@H](COc1cccc2c1cccc2)CNC(C)C
InChI InChI=1S/C16H21NO2/c1-12(2)17-10-14(18)11-19-16-9-5-7-13-6-3-4-8-15(13)16/h3-9,12,14,17-18H,10-11H2,1-2H3/t14-/m0/s1
InChI Key AQHHHDLHHXJYJD-AWEZNQCLSA-N
References
1. Baker JG. (2005)
The selectivity of beta-adrenoceptor antagonists at the human beta1, beta2 and beta3 adrenoceptors.
Br. J. Pharmacol., 144 (3): 317-22. [PMID:15655528]
2. Joseph SS, Lynham JA, Colledge WH, Kaumann AJ. (2004)
Binding of (-)-[3H]-CGP12177 at two sites in recombinant human beta 1-adrenoceptors and interaction with beta-blockers.
Naunyn Schmiedebergs Arch. Pharmacol., 369 (5): 525-32. [PMID:15060759]
3. Kim RB, Leake B, Cvetkovic M, Roden MM, Nadeau J, Walubo A, Wilkinson GR. (1999)
Modulation by drugs of human hepatic sodium-dependent bile acid transporter (sodium taurocholate cotransporting polypeptide) activity.
J. Pharmacol. Exp. Ther., 291 (3): 1204-9. [PMID:10565843]
4. Louis SN, Nero TL, Iakovidis D, Jackman GP, Louis WJ. (1999)
LK 204-545, a highly selective beta1-adrenoceptor antagonist at human beta-adrenoceptors.
Eur. J. Pharmacol., 367 (2-3): 431-5. [PMID:10079020]
5. Newman-Tancredi A, Conte C, Chaput C, Verrièle L, Audinot-Bouchez V, Lochon S, Lavielle G, Millan MJ. (1997)
Agonist activity of antimigraine drugs at recombinant human 5-HT1A receptors: potential implications for prophylactic and acute therapy.
Naunyn Schmiedebergs Arch. Pharmacol., 355 (6): 682-8. [PMID:9205951]
6. Rees S, den Daas I, Foord S, Goodson S, Bull D, Kilpatrick G, Lee M. (1994)
Cloning and characterisation of the human 5-HT5A serotonin receptor.
FEBS Lett., 355 (3): 242-6. [PMID:7988681]