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))
Compound class: Metabolite
Comment: Dopamine is the precursor to norepinephrine (noradrenaline) and epinephrine ((±)-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: dopamine

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 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
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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 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
References
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Trace amines: identification of a family of mammalian G protein-coupled receptors.
Proc Natl Acad Sci USA, 98 (16): 8966-71. [PMID:11459929]
2. Burris KD, Pacheco MA, Filtz TM, Kung MP, Kung HF, Molinoff PB. (1995)
Lack of discrimination by agonists for D2 and D3 dopamine receptors.
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3. Engel K, Wang J. (2005)
Interaction of organic cations with a newly identified plasma membrane monoamine transporter.
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4. Erickson JD, Schafer MK, Bonner TI, Eiden LE, Weihe E. (1996)
Distinct pharmacological properties and distribution in neurons and endocrine cells of two isoforms of the human vesicular monoamine transporter.
Proc Natl Acad Sci USA, 93 (10): 5166-71. [PMID:8643547]
5. Freedman SB, Patel S, Marwood R, Emms F, Seabrook GR, Knowles MR, McAllister G. (1994)
Expression and pharmacological characterization of the human D3 dopamine receptor.
J Pharmacol Exp Ther, 268 (1): 417-26. [PMID:8301582]
6. Gründemann D, Liebich G, Kiefer N, Köster S, Schömig E. (1999)
Selective substrates for non-neuronal monoamine transporters.
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7. Sautel F, Griffon N, Lévesque D, Pilon C, Schwartz JC, Sokoloff P. (1995)
A functional test identifies dopamine agonists selective for D3versus D2receptors.
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8. Schetz JA, Benjamin PS, Sibley DR. (2000)
Nonconserved residues in the second transmembrane-spanning domain of the D(4) dopamine receptor are molecular determinants of D(4)-selective pharmacology.
Mol Pharmacol, 57 (1): 144-52. [PMID:10617689]
9. Shao W, Zhang SZ, Tang M, Zhang XH, Zhou Z, Yin YQ, Zhou QB, Huang YY, Liu YJ, Wawrousek E et al.. (2013)
Suppression of neuroinflammation by astrocytic dopamine D2 receptors via αB-crystallin.
Nature, 494 (7435): 90-4. [PMID:23242137]
10. Sokoloff P, Giros B, Martres MP, Bouthenet ML, Schwartz JC. (1990)
Molecular cloning and characterization of a novel dopamine receptor (D3) as a target for neuroleptics.
Nature, 347 (6289): 146-51. [PMID:1975644]
11. Sunahara RK, Guan HC, O'Dowd BF, Seeman P, Laurier LG, Ng G, George SR, Torchia J, Van Tol HH, Niznik HB. (1991)
Cloning of the gene for a human dopamine D5 receptor with higher affinity for dopamine than D1.
Nature, 350 (6319): 614-9. [PMID:1826762]
12. Tiberi M, Caron MG. (1994)
High agonist-independent activity is a distinguishing feature of the dopamine D1B receptor subtype.
J Biol Chem, 269 (45): 27925-31. [PMID:7525564]
13. Van Tol HH, Bunzow JR, Guan HC, Sunahara RK, Seeman P, Niznik HB, Civelli O. (1991)
Cloning of the gene for a human dopamine D4 receptor with high affinity for the antipsychotic clozapine.
Nature, 350 (6319): 610-4. [PMID:1840645]
14. Wang J. (2016)
The plasma membrane monoamine transporter (PMAT): Structure, function, and role in organic cation disposition.
Clin Pharmacol Ther, 100 (5): 489-499. [PMID:27506881]
15. Yan Y, Jiang W, Liu L, Wang X, Ding C, Tian Z, Zhou R. (2015)
Dopamine controls systemic inflammation through inhibition of NLRP3 inflammasome.
Cell, 160 (1-2): 62-73. [PMID:25594175]
16. Zhang Y, Jiang X, Qin C, Cuevas S, Jose PA, Armando I. (2016)
Dopamine D2 receptors' effects on renal inflammation are mediated by regulation of PP2A function.
Am J Physiol Renal Physiol, 310 (2): F128-34. [PMID:26290374]
17. Zhu HJ, Appel DI, Gründemann D, Markowitz JS. (2010)
Interaction of organic cation transporter 3 (SLC22A3) and amphetamine.
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