(-)-adrenaline   Click here for help

GtoPdb Ligand ID: 479

Synonyms: adrenalin | Auvi-Q® | Epipen® | l-adrenaline | L-epinephrine | levoepinephrine
Approved drug PDB Ligand Immunopharmacology Ligand
(-)-adrenaline is an approved drug (FDA (no history prior to 1951))
Compound class: Metabolite or derivative
Comment: Agonist at alpha and beta adrenoceptors. In addition to being assigned the INN epinephrine in its own right, (-)-adrenaline is also one of the enantiomers found in the INN-assigned compound (±)-adrenaline.
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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: adrenaline

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 3
Topological polar surface area 72.72
Molecular weight 183.09
XLogP 0.28
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 CNCC(c1ccc(c(c1)O)O)O
Isomeric SMILES CNC[C@@H](c1ccc(c(c1)O)O)O
InChI InChI=1S/C9H13NO3/c1-10-5-9(13)6-2-3-7(11)8(12)4-6/h2-4,9-13H,5H2,1H3/t9-/m0/s1
InChI Key UCTWMZQNUQWSLP-VIFPVBQESA-N
Natural/Endogenous Targets
Target
α1A-adrenoceptor
α1B-adrenoceptor
α1D-adrenoceptor
α2A-adrenoceptor
α2B-adrenoceptor
α2C-adrenoceptor
β1-adrenoceptor
β2-adrenoceptor
β3-adrenoceptor
Enzymes Catalysing Reactions with this Compound as a Substrate or Product
Enzyme EC number Reaction Reference
Catechol-O-methyltransferase 2.1.1.6 (-)-Adrenaline -> metanephrine
Phenylethanolamine N-methyltransferase 2.1.1.28 (-)-Noradrenaline -> (-)-adrenaline
Monoamine oxidase A 1.4.3.4 (-)-Adrenaline -> 3,4-dihydroxymandelic acid + NH3
Monoamine oxidase B 1.4.3.4 (-)-Adrenaline -> 3,4-dihydroxymandelic acid + NH3
Transporters Moving this Compound Across a Lipid Membrane
Transporter EC number Reaction Reference
NET
DAT
Vesicular monoamine transporter 1 2
Vesicular monoamine transporter 2 2
Selectivity at GPCRs
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
α1D-adrenoceptor Ligand is endogenous in the given species Rn Agonist Full agonist 6.3 pKi - 8
⤷ pKi 6.3 [8]
α1D-adrenoceptor Primary target of this compound Ligand is endogenous in the given species Hs Agonist Full agonist 5.3 – 7.2 pKi - 5,11,13
⤷ pKi 5.3 – 7.2 [5,11,13]
β2-adrenoceptor Ligand is endogenous in the given species Hs Agonist Full agonist 6.0 – 6.2 pKi - 1,3-4,6
⤷ pKi 6.0 – 6.2 [1,3-4,6]
α1A-adrenoceptor Ligand is endogenous in the given species Hs Agonist Full agonist 5.1 – 6.5 pKi - 5,11-13
⤷ pKi 5.1 – 6.5 [5,11-13]
β1-adrenoceptor Ligand is endogenous in the given species Hs Agonist Agonist 5.2 – 6.0 pKi - 1,3-4
⤷ pKi 5.2 – 6.0 [1,3-4]
α2A-adrenoceptor Primary target of this compound Ligand is endogenous in the given species Hs Agonist Full agonist 3.7 – 7.4 pKi - 7,9-10
⤷ pKi 3.7 – 7.4 [7,9-10]
α2C-adrenoceptor Ligand is endogenous in the given species Hs Agonist Full agonist 4.9 – 5.8 pKi - 7,10
⤷ pKi 4.9 – 5.8 [7,10]
α1B-adrenoceptor Ligand is endogenous in the given species Hs Agonist Full agonist 3.9 – 6.5 pKi - 11,13
⤷ pKi 3.9 – 6.5 [11,13]
α2B-adrenoceptor Ligand is endogenous in the given species Hs Agonist Full agonist 3.6 – 5.2 pKi - 7,10
⤷ pKi 3.6 – 5.2 [7,10]
β3-adrenoceptor Ligand is endogenous in the given species Hs Agonist Full agonist 3.9 – 4.7 pKi - 1,4
⤷ pKi 3.9 – 4.7 [1,4]
β2-adrenoceptor Hs Agonist Full agonist 7.9 pEC50 - 1
⤷ pEC50 7.9 [1]
α2C-adrenoceptor Hs Agonist Full agonist 7.6 pEC50 - 10
⤷ pEC50 7.6 [10]
Description: ERK1/2 phosphorylation
β1-adrenoceptor Hs Agonist Agonist 7.6 pEC50 - 1
⤷ pEC50 7.6 [1]
α1B-adrenoceptor Hs Agonist Full agonist 5.4 – 9.4 pEC50 - 11
⤷ pEC50 5.4 – 9.4 [11]
α1A-adrenoceptor Hs Agonist Full agonist 5.6 – 9.1 pEC50 - 11
⤷ pEC50 5.6 – 9.1 [11]
α1D-adrenoceptor Hs Agonist Full agonist 6.7 – 7.7 pEC50 - 11
⤷ pEC50 6.7 – 7.7 [11]
α2B-adrenoceptor Hs Agonist Full agonist 6.3 – 7.5 pEC50 - 10
⤷ pEC50 7.5 [10]
Description: ERK1/2 phosphorylation
pEC50 6.3 [10]
Description: cAMP generation
α2A-adrenoceptor Hs Agonist Full agonist 5.5 – 8.0 pEC50 - 7,10
⤷ pEC50 8.0 [10]
Description: increased ERK1/2 phosphorylation
pEC50 6.8 [7]
Description: GTPγs binding
pEC50 5.5 [10]
Description: increased cAMP generation
β3-adrenoceptor Hs Agonist Full agonist 6.5 pEC50 - 1
⤷ pEC50 6.5 [1]
α2B-adrenoceptor Hs Agonist Full agonist 7.6 pIC50 - 10
⤷ pIC50 7.6 [10]
Description: inhibition of forskolin stimulated cAMP generation
α2C-adrenoceptor Hs Agonist Full agonist 6.7 pIC50 - 10
⤷ pIC50 6.7 [10]
Description: inhibition of cAMP production
α2A-adrenoceptor Hs Agonist Full agonist 6.5 pIC50 - 10
⤷ pIC50 6.5 [10]
Description: inhibition of forskolin stimulated cAMP generation
Selectivity at enzymes
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
carbonic anhydrase 1 Hs Activator Activation - - - 14
⤷ KA 90 nM [14]
Additional information and targets (data relate to human unless otherwise stated)
Description Data Reference
Potency order of endogenous ligands at β2-adrenoceptor (-)-adrenaline > (-)-noradrenaline
Potency order of endogenous ligands at β3-adrenoceptor (-)-noradrenaline = (-)-adrenaline
Potency order of endogenous ligands at β1-adrenoceptor (-)-noradrenaline > (-)-adrenaline
Potency order of endogenous ligands at α1A-adrenoceptor (-)-noradrenaline = (-)-adrenaline
Ligand mentioned in the following text fields
Adrenoceptors overview
Catecholamine turnover overview