tryptamine   Click here for help

GtoPdb Ligand ID: 125

PDB Ligand
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 2
Rotatable bonds 2
Topological polar surface area 41.81
Molecular weight 160.1
XLogP 1.41
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 NCCc1c[nH]c2c1cccc2
Isomeric SMILES NCCc1c[nH]c2c1cccc2
InChI InChI=1S/C10H12N2/c11-6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5-6,11H2
InChI Key APJYDQYYACXCRM-UHFFFAOYSA-N
References
1. Adham N, Kao HT, Schecter LE, Bard J, Olsen M, Urquhart D, Durkin M, Hartig PR, Weinshank RL, Branchek TA. (1993)
Cloning of another human serotonin receptor (5-HT1F): a fifth 5-HT1 receptor subtype coupled to the inhibition of adenylate cyclase.
Proc Natl Acad Sci USA, 90 (2): 408-12. [PMID:8380639]
2. Bai F, Yin T, Johnstone EM, Su C, Varga G, Little SP, Nelson DL. (2004)
Molecular cloning and pharmacological characterization of the guinea pig 5-HT1E receptor.
Eur J Pharmacol, 484 (2-3): 127-39. [PMID:14744596]
3. Bard JA, Zgombick J, Adham N, Vaysse P, Branchek TA, Weinshank RL. (1993)
Cloning of a novel human serotonin receptor (5-HT7) positively linked to adenylate cyclase.
J Biol Chem, 268 (31): 23422-6. [PMID:8226867]
4. Boess FG, Monsma Jr FJ, Carolo C, Meyer V, Rudler A, Zwingelstein C, Sleight AJ. (1997)
Functional and radioligand binding characterization of rat 5-HT6 receptors stably expressed in HEK293 cells.
Neuropharmacology, 36 (4-5): 713-20. [PMID:9225298]
5. 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]
6. Branchek T, Adham N, Macchi M, Kao HT, Hartig PR. (1990)
[3H]-DOB(4-bromo-2,5-dimethoxyphenylisopropylamine) and [3H] ketanserin label two affinity states of the cloned human 5-hydroxytryptamine2 receptor.
Mol Pharmacol, 38 (5): 604-9. [PMID:2233697]
7. Dukat M, Smith C, Herrick-Davis K, Teitler M, Glennon RA. (2004)
Binding of tryptamine analogs at h5-HT1E receptors: a structure-affinity investigation.
Bioorg Med Chem, 12 (10): 2545-52. [PMID:15110837]
8. Egan C, Grinde E, Dupre A, Roth BL, Hake M, Teitler M, Herrick-Davis K. (2000)
Agonist high and low affinity state ratios predict drug intrinsic activity and a revised ternary complex mechanism at serotonin 5-HT(2A) and 5-HT(2C) receptors.
Synapse, 35: 144-150. [PMID:10611640]
9. Johnson MP, Loncharich RJ, Baez M, Nelson DL. (1994)
Species variations in transmembrane region V of the 5-hydroxytryptamine type 2A receptor alter the structure-activity relationship of certain ergolines and tryptamines.
Mol Pharmacol, 45 (2): 277-86. [PMID:8114677]
10. Knight AR, Misra A, Quirk K, Benwell K, Revell D, Kennett G, Bickerdike M. (2004)
Pharmacological characterisation of the agonist radioligand binding site of 5-HT(2A), 5-HT(2B) and 5-HT(2C) receptors.
Naunyn Schmiedebergs Arch Pharmacol, 370 (2): 114-23. [PMID:15322733]
11. Leysen JE, Gommeren W, Heylen L, Luyten WH, Van de Weyer I, Vanhoenacker P, Haegeman G, Schotte A, Van Gompel P, Wouters R et al.. (1996)
Alniditan, a new 5-hydroxytryptamine1D agonist and migraine-abortive agent: ligand-binding properties of human 5-hydroxytryptamine1D alpha, human 5-hydroxytryptamine1D beta, and calf 5-hydroxytryptamine1D receptors investigated with [3H]5-hydroxytryptamine and [3H]alniditan.
Mol Pharmacol, 50 (6): 1567-80. [PMID:8967979]
12. Monsma Jr FJ, Shen Y, Ward RP, Hamblin MW, Sibley DR. (1993)
Cloning and expression of a novel serotonin receptor with high affinity for tricyclic psychotropic drugs.
Mol Pharmacol, 43 (3): 320-7. [PMID:7680751]
13. Shen Y, Monsma Jr FJ, Metcalf MA, Jose PA, Hamblin MW, Sibley DR. (1993)
Molecular cloning and expression of a 5-hydroxytryptamine7 serotonin receptor subtype.
J Biol Chem, 268 (24): 18200-4. [PMID:8394362]
14. Wainscott DB, Cohen ML, Schenck KW, Audia JE, Nissen JS, Baez M, Kursar JD, Lucaites VL, Nelson DL. (1993)
Pharmacological characteristics of the newly cloned rat 5-hydroxytryptamine2F receptor.
Mol Pharmacol, 43 (3): 419-26. [PMID:8450835]
15. Weinshank RL, Zgombick JM, Macchi MJ, Branchek TA, Hartig PR. (1992)
Human serotonin 1D receptor is encoded by a subfamily of two distinct genes: 5-HT1D alpha and 5-HT1D beta.
Proc Natl Acad Sci USA, 89 (8): 3630-4. [PMID:1565658]