octopamine   Click here for help

GtoPdb Ligand ID: 2149

Comment: Please note that the two PDB links in the table above represent (R)-octopamine and (S)-octopamine respectively. All other database entries linked to above do not specify stereochemistry.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 2
Hydrogen bond donors 3
Rotatable bonds 2
Topological polar surface area 66.48
Molecular weight 153.08
XLogP 0.13
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES NCC(c1ccc(cc1)O)O
Isomeric SMILES NCC(c1ccc(cc1)O)O
InChI InChI=1S/C8H11NO2/c9-5-8(11)6-1-3-7(10)4-2-6/h1-4,8,10-11H,5,9H2
InChI Key QHGUCRYDKWKLMG-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. U.S.A., 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. 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]
5. 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]
6. 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]
7. 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]