dopamine   Click here for help

GtoPdb Ligand ID: 940

Synonyms: 3-hydroxytyramine
Approved drug PDB Ligand Immunopharmacology Ligand
dopamine is an approved drug (FDA (1974))
Comment: Dopamine is the precursor to norepinephrine (noradrenaline) and epinephrine ((±)-adrenaline).
Click here for help
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: dopamine

2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 1
Hydrogen bond donors 3
Rotatable bonds 2
Topological polar surface area 66.48
Molecular weight 153.08
XLogP 0.65
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Click here for help
Canonical SMILES NCCc1ccc(c(c1)O)O
Isomeric SMILES NCCc1ccc(c(c1)O)O
InChI InChI=1S/C8H11NO2/c9-4-3-6-1-2-7(10)8(11)5-6/h1-2,5,10-11H,3-4,9H2
InChI Key VYFYYTLLBUKUHU-UHFFFAOYSA-N
Natural/Endogenous Targets
Target
D1 receptor
D2 receptor
D3 receptor
D4 receptor
D5 receptor
TA1 receptor
Enzymes Catalysing Reactions with this Compound as a Substrate or Product
Enzyme EC number Reaction Reference
L-Aromatic amino-acid decarboxylase
Monoamine oxidase A
Dopamine beta-hydroxylase (dopamine beta-monooxygenase)
Catechol-O-methyltransferase
Monoamine oxidase B
Transporters Moving this Compound Across a Lipid Membrane
Transporter EC number Reaction Reference
Organic cation transporter 2 6
DAT
NET
Vesicular monoamine transporter 1 4
Vesicular monoamine transporter 2 4
Organic cation transporter 3 17
Plasma membrane monoamine transporter 3,14
Selectivity at GPCRs
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
D4 receptor Primary target of this compound Ligand is endogenous in the given species Hs Agonist Full agonist 7.6 pKi - 13
pKi 7.6 [13]
D4 receptor Ligand is endogenous in the given species Rn Agonist Full agonist 7.4 pKi - 8
pKi 7.4 [8]
D3 receptor Primary target of this compound Ligand is endogenous in the given species Hs Agonist Full agonist 6.4 – 7.3 pKi - 2,5,7,10
pKi 6.4 – 7.3 [2,5,7,10]
D5 receptor Primary target of this compound Ligand is endogenous in the given species Hs Agonist Full agonist 6.6 pKi - 11
pKi 6.6 [11]
D2 receptor Primary target of this compound Ligand is endogenous in the given species Hs Agonist Full agonist 4.7 – 7.2 pKi - 2,5,7
pKi 4.7 – 7.2 [2,5,7]
D2 receptor Ligand is endogenous in the given species Rn Agonist Full agonist 5.3 – 6.4 pKi - 8,10
pKi 5.3 – 6.4 [8,10]
D1 receptor Primary target of this compound Ligand is endogenous in the given species Hs Agonist Full agonist 4.3 – 5.6 pKi - 11-12
pKi 4.3 – 5.6 [11-12]
Additional information and targets (data relate to human unless otherwise stated)
Description Data Reference
Ligand mentioned in the following text fields