(-)-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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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Click here for structure editor
Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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]
7. Soave M, Stoddart LA, Brown A, Woolard J, Hill SJ. (2016)
Use of a new proximity assay (NanoBRET) to investigate the ligand-binding characteristics of three fluorescent ligands to the human β1-adrenoceptor expressed in HEK-293 cells.
Pharmacol Res Perspect, 4 (5): e00250. [PMID:27588207]