tegaserod   Click here for help

GtoPdb Ligand ID: 226

Synonyms: HTF 919 | SDZ HTF 919 | Zelnorm®
Approved drug
tegaserod is an approved drug (FDA (2002))
Compound class: Synthetic organic
Comment: There is some ambiguity as to the exact structure of tegaserod. The structure shown here is PubChem match using the CAS number submitted to the WHO for the INN. Alternative structure renderings for tegaserod are numerous: PubChem CID 5362436 has the highest submitter consensus in PubChem but may not match renderings in references for the biological activity; CID 5487301, and CHEMBL76370 are further alternatives.
Marketed formulations include tegaserod maleate (PubChem CID 6918369)- again with the caveat of alternative representations.
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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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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 4
Hydrogen bond donors 3
Rotatable bonds 8
Topological polar surface area 87.79
Molecular weight 301.19
XLogP 4.2
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 CCCCCN=C(N/N=C/c1c[nH]c2c1cc(OC)cc2)N
Isomeric SMILES CCCCCN=C(N/N=C/c1c[nH]c2c1cc(OC)cc2)N
InChI InChI=1S/C16H23N5O/c1-3-4-5-8-18-16(17)21-20-11-12-10-19-15-7-6-13(22-2)9-14(12)15/h6-7,9-11,19H,3-5,8H2,1-2H3,(H3,17,18,21)/b20-11+
InChI Key IKBKZGMPCYNSLU-RGVLZGJSSA-N
References
1. Beattie DT, Smith JA, Marquess D, Vickery RG, Armstrong SR, Pulido-Rios T, McCullough JL, Sandlund C, Richardson C, Mai N et al.. (2004)
The 5-HT4 receptor agonist, tegaserod, is a potent 5-HT2B receptor antagonist in vitro and in vivo.
Br J Pharmacol, 143 (5): 549-60. [PMID:15466450]
2. Bender E, Pindon A, van Oers I, Zhang YB, Gommeren W, Verhasselt P, Jurzak M, Leysen J, Luyten W. (2000)
Structure of the human serotonin 5-HT4 receptor gene and cloning of a novel 5-HT4 splice variant.
J Neurochem, 74 (2): 478-89. [PMID:10646498]