(-)-noradrenaline   Click here for help

GtoPdb Ligand ID: 505

Synonyms: (-)-norepinephrine | Levarterenol® | noradrenaline
Approved drug PDB Ligand
(-)-noradrenaline is an approved drug (FDA (1950))
Compound class: Metabolite or derivative
Comment: Marketed formulations may contain noradrenaline tartrate (PubChem CID 25127519).
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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

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View more information in the IUPHAR Pharmacology Education Project: noradrenaline

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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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 4
Rotatable bonds 2
Topological polar surface area 86.71
Molecular weight 169.07
XLogP -0.11
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 NCC(c1ccc(c(c1)O)O)O
Isomeric SMILES NC[C@@H](c1ccc(c(c1)O)O)O
InChI InChI=1S/C8H11NO3/c9-4-8(12)5-1-2-6(10)7(11)3-5/h1-3,8,10-12H,4,9H2/t8-/m0/s1
InChI Key SFLSHLFXELFNJZ-QMMMGPOBSA-N
References
1. Baker JG. (2010)
The selectivity of beta-adrenoceptor agonists at human beta1-, beta2- and beta3-adrenoceptors.
Br J Pharmacol, 160 (5): 1048-61. [PMID:20590599]
2. da Silva Junior ED, Sato M, Merlin J, Broxton N, Hutchinson DS, Ventura S, Evans BA, Summers RJ. (2017)
Factors influencing biased agonism in recombinant cells expressing the human α1A -adrenoceptor.
Br J Pharmacol, 174 (14): 2318-2333. [PMID:28444738]
3. Erickson JD, Schafer MK, Bonner TI, Eiden LE, Weihe E. (1996)
Distinct pharmacological properties and distribution in neurons and endocrine cells of two isoforms of the human vesicular monoamine transporter.
Proc Natl Acad Sci USA, 93 (10): 5166-71. [PMID:8643547]
4. Evans BA, Broxton N, Merlin J, Sato M, Hutchinson DS, Christopoulos A, Summers RJ. (2011)
Quantification of functional selectivity at the human α(1A)-adrenoceptor.
Mol Pharmacol, 79 (2): 298-307. [PMID:20978120]
5. Frielle T, Daniel KW, Caron MG, Lefkowitz RJ. (1988)
Structural basis of beta-adrenergic receptor subtype specificity studied with chimeric beta 1/beta 2-adrenergic receptors.
Proc Natl Acad Sci USA, 85 (24): 9494-8. [PMID:2849109]
6. Hoffmann C, Leitz MR, Oberdorf-Maass S, Lohse MJ, Klotz KN. (2004)
Comparative pharmacology of human beta-adrenergic receptor subtypes--characterization of stably transfected receptors in CHO cells.
Naunyn Schmiedebergs Arch Pharmacol, 369 (2): 151-9. [PMID:14730417]
7. Horie K, Obika K, Foglar R, Tsujimoto G. (1995)
Selectivity of the imidazoline alpha-adrenoceptor agonists (oxymetazoline and cirazoline) for human cloned alpha 1-adrenoceptor subtypes.
Br J Pharmacol, 116 (1): 1611-8. [PMID:8564227]
8. Jasper JR, Lesnick JD, Chang LK, Yamanishi SS, Chang TK, Hsu SA, Daunt DA, Bonhaus DW, Eglen RM. (1998)
Ligand efficacy and potency at recombinant alpha2 adrenergic receptors: agonist-mediated [35S]GTPgammaS binding.
Biochem Pharmacol, 55 (7): 1035-43. [PMID:9605427]
9. Kurko D, Kapui Z, Nagy J, Lendvai B, Kolok S. (2014)
Analysis of functional selectivity through G protein-dependent and -independent signaling pathways at the adrenergic α(2C) receptor.
Brain Res Bull, 107: 89-101. [PMID:25080296]
10. Minneman KP, Theroux TL, Hollinger S, Han C, Esbenshade TA. (1994)
Selectivity of agonists for cloned alpha 1-adrenergic receptor subtypes.
Mol Pharmacol, 46 (5): 929-36. [PMID:7969082]
11. Pihlavisto M, Sjöholm B, Scheinin M, Wurster S. (1998)
Modulation of agonist binding to recombinant human alpha2-adrenoceptors by sodium ions.
Biochim Biophys Acta, 1448 (1): 135-46. [PMID:9824686]
12. Popp BD, Hutchinson DS, Evans BA, Summers RJ. (2004)
Stereoselectivity for interactions of agonists and antagonists at mouse, rat and human beta3-adrenoceptors.
Eur J Pharmacol, 484 (2-3): 323-31. [PMID:14744619]
13. Proudman RGW, Akinaga J, Baker JG. (2022)
The signaling and selectivity of α-adrenoceptor agonists for the human α2A, α2B and α2C-adrenoceptors and comparison with human α1 and β-adrenoceptors.
Pharmacol Res Perspect, 10 (5): e01003. [PMID:36101495]
14. Proudman RGW, Baker JG. (2021)
The selectivity of α-adrenoceptor agonists for the human α1A, α1B, and α1D-adrenoceptors.
Pharmacol Res Perspect, 9 (4): e00799. [PMID:34355529]
15. Schwinn DA, Johnston GI, Page SO, Mosley MJ, Wilson KH, Worman NP, Campbell S, Fidock MD, Furness LM, Parry-Smith DJ et al.. (1995)
Cloning and pharmacological characterization of human alpha-1 adrenergic receptors: sequence corrections and direct comparison with other species homologues.
J Pharmacol Exp Ther, 272 (1): 134-42. [PMID:7815325]
16. Shibata K, Foglar R, Horie K, Obika K, Sakamoto A, Ogawa S, Tsujimoto G. (1995)
KMD-3213, a novel, potent, alpha 1a-adrenoceptor-selective antagonist: characterization using recombinant human alpha 1-adrenoceptors and native tissues.
Mol Pharmacol, 48 (2): 250-8. [PMID:7651358]
17. Strosberg AD. (1997)
Structure and function of the beta 3-adrenergic receptor.
Annu Rev Pharmacol Toxicol, 37: 421-50. [PMID:9131260]
18. Taniguchi T, Inagaki R, Murata S, Akiba I, Muramatsu I. (1999)
Microphysiometric analysis of human alpha1a-adrenoceptor expressed in Chinese hamster ovary cells.
Br J Pharmacol, 127 (4): 962-8. [PMID:10433504]
19. Zhu HJ, Appel DI, Gründemann D, Markowitz JS. (2010)
Interaction of organic cation transporter 3 (SLC22A3) and amphetamine.
J Neurochem, 114 (1): 142-9. [PMID:20402963]