β-phenylethylamine   Click here for help

GtoPdb Ligand ID: 2144

Abbreviated name: PEA
Synonyms: β-PEA | 2-phenylethylamine | phenethylamine
Compound class: Metabolite or derivative
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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
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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Click here for structure editor
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 1
Rotatable bonds 2
Topological polar surface area 26.02
Molecular weight 121.09
XLogP 1.3
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 NCCc1ccccc1
Isomeric SMILES NCCc1ccccc1
InChI InChI=1S/C8H11N/c9-7-6-8-4-2-1-3-5-8/h1-5H,6-7,9H2
InChI Key BHHGXPLMPWCGHP-UHFFFAOYSA-N
References
1. Barak LS, Salahpour A, Zhang X, Masri B, Sotnikova TD, Ramsey AJ, Violin JD, Lefkowitz RJ, Caron MG, Gainetdinov RR. (2008)
Pharmacological characterization of membrane-expressed human trace amine-associated receptor 1 (TAAR1) by a bioluminescence resonance energy transfer cAMP biosensor.
Mol Pharmacol, 74 (3): 585-594. [PMID:18524885]
2. Borowsky B, Adham N, Jones KA, Raddatz R, Artymyshyn R, Ogozalek KL, Durkin MM, Lakhlani PP, Bonini JA, Pathirana S et al.. (2001)
Trace amines: identification of a family of mammalian G protein-coupled receptors.
Proc Natl Acad Sci USA, 98 (16): 8966-71. [PMID:11459929]
3. Bunzow JR, Sonders MS, Arttamangkul S, Harrison LM, Zhang G, Quigley DI, Darland T, Suchland KL, Pasumamula S, Kennedy JL et al.. (2001)
Amphetamine, 3,4-methylenedioxymethamphetamine, lysergic acid diethylamide, and metabolites of the catecholamine neurotransmitters are agonists of a rat trace amine receptor.
Mol Pharmacol, 60 (6): 1181-8. [PMID:11723224]
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. Hu LA, Zhou T, Ahn J, Wang S, Zhou J, Hu Y, Liu Q. (2009)
Human and mouse trace amine-associated receptor 1 have distinct pharmacology towards endogenous monoamines and imidazoline receptor ligands.
Biochem J, 424 (1): 39-45. [PMID:19725810]
6. Kleinau G, Pratzka J, Nürnberg D, Grüters A, Führer-Sakel D, Krude H, Köhrle J, Schöneberg T, Biebermann H. (2011)
Differential modulation of Beta-adrenergic receptor signaling by trace amine-associated receptor 1 agonists.
PLoS ONE, 6 (10): e27073. [PMID:22073124]
7. Lewin AH, Navarro HA, Mascarella SW. (2008)
Structure-activity correlations for beta-phenethylamines at human trace amine receptor 1.
Bioorg Med Chem, 16 (15): 7415-23. [PMID:18602830]
8. Liberles SD, Buck LB. (2006)
A second class of chemosensory receptors in the olfactory epithelium.
Nature, 442: 645-650. [PMID:16878137]
9. Reese EA, Bunzow JR, Arttamangkul S, Sonders MS, Grandy DK. (2007)
Trace amine-associated receptor 1 displays species-dependent stereoselectivity for isomers of methamphetamine, amphetamine, and para-hydroxyamphetamine.
J Pharmacol Exp Ther, 321 (1): 178-86. [PMID:17218486]
10. Stäubert C, Böselt I, Bohnekamp J, Römpler H, Enard W, Schöneberg T. (2010)
Structural and functional evolution of the trace amine-associated receptors TAAR3, TAAR4 and TAAR5 in primates.
PLoS ONE, 5 (6): e11133. [PMID:20559446]
11. Wainscott DB, Little SP, Yin T, Tu Y, Rocco VP, He JX, Nelson DL. (2007)
Pharmacologic characterization of the cloned human trace amine-associated receptor1 (TAAR1) and evidence for species differences with the rat TAAR1.
J Pharmacol Exp Ther, 320 (1): 475-85. [PMID:17038507]
12. Wolinsky TD, Swanson CJ, Smith KE, Zhong H, Borowsky B, Seeman P, Branchek T, Gerald CP. (2007)
The Trace Amine 1 receptor knockout mouse: an animal model with relevance to schizophrenia.
Genes Brain Behav, 6 (7): 628-39. [PMID:17212650]