(-)-noradrenaline   Click here for help

GtoPdb Ligand ID: 505

Synonyms: (-)-norepinephrine | Levarterenol® | noradrenaline
Approved drug PDB Ligand
(-)-noradrenaline is an approved drug (FDA (1950))
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
Monoamine oxidase A
Dopamine beta-hydroxylase (dopamine beta-monooxygenase)
Catechol-O-methyltransferase
Phenylethanolamine N-methyltransferase
Monoamine oxidase B
Transporters Moving this Compound Across a Lipid Membrane
Transporter EC number Reaction Reference
Vesicular monoamine transporter 1 1
Vesicular monoamine transporter 2 1
Organic cation transporter 3 12
DAT
NET
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 7.4 pKi - 4,9
pKi 7.4 [4,9]
α2A-adrenoceptor Ligand is endogenous in the given species Hs Agonist Full agonist 5.6 – 7.4 pKi - 5,7
pKi 5.6 – 7.4 [5,7]
α1D-adrenoceptor Ligand is endogenous in the given species Rn Agonist Full agonist 6.3 pKi - 6
pKi 6.3 [6]
α2C-adrenoceptor Primary target of this compound Ligand is endogenous in the given species Hs Agonist Full agonist 5.7 – 6.8 pKi - 5,7
pKi 5.7 – 6.8 [5,7]
α1B-adrenoceptor Ligand is endogenous in the given species Hs Agonist Full agonist 6.2 pKi - 9
pKi 6.2 [9]
α1A-adrenoceptor Ligand is endogenous in the given species Hs Agonist Full agonist 5.8 – 6.4 pKi - 4,9,11
pKi 5.8 – 6.4 [4,9,11]
β1-adrenoceptor Ligand is endogenous in the given species Hs Agonist Agonist 5.5 – 6.0 pKi - 2-3
pKi 5.5 – 6.0 [2-3]
α2B-adrenoceptor Primary target of this compound Ligand is endogenous in the given species Hs Agonist Partial agonist 5.4 – 6.0 pKi - 5,7
pKi 5.4 – 6.0 [5,7]
β3-adrenoceptor Ligand is endogenous in the given species Hs Agonist Full agonist 4.7 – 6.3 pKi - 3,8,10
pKi 4.7 – 6.3 [3,8,10]
β2-adrenoceptor Ligand is endogenous in the given species Hs Agonist Agonist 4.6 – 4.8 pKi - 2-3
pKi 4.6 – 4.8 [2-3]
β3-adrenoceptor Ligand is endogenous in the given species Rn Agonist Full agonist 4.2 pKi - 8
pKi 4.2 [8]
β3-adrenoceptor Ligand is endogenous in the given species Mm Agonist Full agonist 3.8 pKi - 8
pKi 3.8 [8]
Additional information and targets (data relate to human unless otherwise stated)
Description Data Reference
Ligand mentioned in the following text fields