(±)-adrenaline   Click here for help

GtoPdb Ligand ID: 509

Synonyms: adrenaline | epinephrine
Comment: The preparation of adrenaline/epinephrine assigned the INN racepinefrine is an racemic mixture of the enantiomers (+)-adrenaline and (-)-adrenaline. The structure shown here does not specify stereochemistry and represents the mixture.
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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 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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Canonical SMILES CNCC(c1ccc(c(c1)O)O)O
Isomeric SMILES CNCC(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
InChI Key UCTWMZQNUQWSLP-UHFFFAOYSA-N
Natural/Endogenous Targets
Target
β3-adrenoceptor
Selectivity at GPCRs
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
α2C-adrenoceptor Hs Agonist Full agonist 5.8 – 6.2 pKi - 4
pKi 5.8 – 6.2 [4]
β1-adrenoceptor Hs Agonist Full agonist 6.0 pKi - 2
pKi 6.0 [2]
α2B-adrenoceptor Hs Agonist Partial agonist 5.2 – 6.2 pKi - 4
pKi 5.2 – 6.2 [4]
β3-adrenoceptor Ligand is endogenous in the given species Mm Agonist Full agonist 5.3 pKi - 5
pKi 5.3 [5]
β3-adrenoceptor Ligand is endogenous in the given species Rn Agonist Full agonist 5.3 pKi - 5
pKi 5.3 [5]
β3-adrenoceptor Ligand is endogenous in the given species Hs Agonist Full agonist 3.9 – 4.7 pKi - 1,3,5
pKi 3.9 – 4.7 [1,3,5]