(-)-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
Selectivity at GPCRs
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
β1-adrenoceptor Primary target of this compound Hs Antagonist Antagonist 8.2 – 8.9 pKi - 1-2,4
pKi 8.2 – 8.9 [1-2,4]
5-HT1A receptor Hs Antagonist Antagonist 7.5 pKi - 5
pKi 7.5 [5]
5-HT5A receptor Hs Antagonist Antagonist 5.1 pKi - 6
pKi 5.1 [6]
Selectivity at transporters
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
Sodium/bile acid and sulphated solute cotransporter 1 Hs Inhibitor Inhibition 8.2 pIC50 - 3
pIC50 8.2 (IC50 6.1x10-9 M) [3]