(-)-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
Comment: Marketed formulations may contain noradrenaline tartrate (PubChem CID 25127519).
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2D Structure
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Physico-chemical Properties
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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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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
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
Phenylethanolamine N-methyltransferase
Monoamine oxidase A
Monoamine oxidase B
Dopamine beta-hydroxylase (dopamine beta-monooxygenase)
Transporters Moving this Compound Across a Lipid Membrane
Transporter EC number Reaction Reference
NET
DAT
Vesicular monoamine transporter 1 3
Vesicular monoamine transporter 2 3
Organic cation transporter 3 19
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 Hs Agonist Full agonist 5.5 – 7.4 pKi - 7,14,16
pKi 5.5 – 7.4 [7,14,16]
α1D-adrenoceptor Ligand is endogenous in the given species Rn Agonist Full agonist 6.3 pKi - 10
pKi 6.3 [10]
β1-adrenoceptor Ligand is endogenous in the given species Hs Agonist Agonist 5.5 – 6.0 pKi - 1,5-6
pKi 5.5 – 6.0 [1,5-6]
α2C-adrenoceptor Primary target of this compound Ligand is endogenous in the given species Hs Agonist Full agonist 4.5 – 6.8 pKi - 8-9,11,13
pKi 4.5 – 6.8 [8-9,11,13]
α1A-adrenoceptor Ligand is endogenous in the given species Hs Agonist Full agonist 4.8 – 6.4 pKi - 2,4,7,14-16,18
pKi 4.8 – 6.4 [2,4,7,14-16,18]
α2A-adrenoceptor Ligand is endogenous in the given species Hs Agonist Full agonist 3.6 – 7.4 pKi - 8,11,13
pKi 3.6 – 7.4 [8,11,13]
β3-adrenoceptor Ligand is endogenous in the given species Hs Agonist Full agonist 4.7 – 6.3 pKi - 6,12,17
pKi 4.7 – 6.3 [6,12,17]
α1B-adrenoceptor Ligand is endogenous in the given species Hs Agonist Full agonist 3.8 – 6.2 pKi - 14,16
pKi 3.8 – 6.2 [14,16]
β2-adrenoceptor Ligand is endogenous in the given species Hs Agonist Agonist 4.6 – 5.4 pKi - 1,5-6
pKi 4.6 – 5.4 [1,5-6]
α2B-adrenoceptor Primary target of this compound Ligand is endogenous in the given species Hs Agonist Full agonist 3.5 – 6.0 pKi - 8,11,13
pKi 3.5 – 6.0 [8,11,13]
β3-adrenoceptor Ligand is endogenous in the given species Rn Agonist Full agonist 4.2 pKi - 12
pKi 4.2 [12]
β3-adrenoceptor Ligand is endogenous in the given species Mm Agonist Full agonist 3.8 pKi - 12
pKi 3.8 [12]
β1-adrenoceptor Hs Agonist Agonist 7.9 pEC50 - 1
pEC50 7.9 [1]
α1B-adrenoceptor Hs Agonist Full agonist 5.9 – 9.2 pEC50 - 14
pEC50 5.9 – 9.2 [14]
α2B-adrenoceptor Hs Agonist Full agonist 6.9 – 7.8 pEC50 - 13
pEC50 7.8 [13]
Description: ERK1/2 phosphorylation
pEC50 6.9 [13]
Description: cAMP generation
α1D-adrenoceptor Hs Agonist Full agonist 6.6 – 7.8 pEC50 - 14
pEC50 6.6 – 7.8 [14]
β3-adrenoceptor Hs Agonist Full agonist 7.2 pEC50 - 1
pEC50 7.2 [1]
α1A-adrenoceptor Hs Agonist Full agonist 5.5 – 8.6 pEC50 - 2,4,14
pEC50 5.5 – 8.6 [2,4,14]
α2C-adrenoceptor Hs Agonist Full agonist 6.0 – 7.7 pEC50 - 9,13
pEC50 7.7 [13]
Description: ERK1/2 phosphorylation
pEC50 6.0 – 6.6 [9]
Description: 6.02 = value for β-arrestin recruitment and internalization
α2A-adrenoceptor Hs Agonist Full agonist 5.3 – 7.7 pEC50 - 8,13
pEC50 7.7 [13]
Description: increased ERK1/2 phosphorylation
pEC50 6.7 [8]
Description: GTPγs binding
pEC50 5.3 [13]
Description: increased cAMP generation
β2-adrenoceptor Hs Agonist Agonist 6.4 pEC50 - 1
pEC50 6.4 [1]
α2B-adrenoceptor Hs Agonist Full agonist 7.8 pIC50 - 13
pIC50 7.8 [13]
Description: inhibition of forskolin stimulated cAMP generation
α2C-adrenoceptor Hs Agonist Full agonist 6.5 – 8.6 pIC50 - 9,13
pIC50 6.5 – 8.6 [9,13]
Description: inhibition of cAMP production
α2A-adrenoceptor Hs Agonist Full agonist 6.6 pIC50 - 13
pIC50 6.6 [13]
Description: inhibition of forskolin stimulated cAMP generation
Additional information and targets (data relate to human unless otherwise stated)
Description Data Reference
Ligand mentioned in the following text fields