osanetant   Click here for help

GtoPdb Ligand ID: 2110

Synonyms: SB-236984 | SR 142,806 | SR 142801 | SR-142,801 | SR-142801 | SR-142806 | SR142801
Compound class: Synthetic organic
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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 5
Hydrogen bond donors 0
Rotatable bonds 10
Topological polar surface area 43.86
Molecular weight 605.26
XLogP 7.05
No. Lipinski's rules broken 1
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 O=C(N1CCCC(C1)(CCCN1CCC(CC1)(c1ccccc1)N(C(=O)C)C)c1ccc(c(c1)Cl)Cl)c1ccccc1
Isomeric SMILES O=C(N1CCC[C@](C1)(CCCN1CCC(CC1)(c1ccccc1)N(C(=O)C)C)c1ccc(c(c1)Cl)Cl)c1ccccc1
InChI InChI=1S/C35H41Cl2N3O2/c1-27(41)38(2)35(29-13-7-4-8-14-29)19-23-39(24-20-35)21-9-17-34(30-15-16-31(36)32(37)25-30)18-10-22-40(26-34)33(42)28-11-5-3-6-12-28/h3-8,11-16,25H,9-10,17-24,26H2,1-2H3/t34-/m0/s1
InChI Key DZOJBGLFWINFBF-UMSFTDKQSA-N
References
1. Anthes JC, Chapman RW, Richard C, Eckel S, Corboz M, Hey JA, Fernandez X, Greenfeder S, McLeod R, Sehring S et al.. (2002)
SCH 206272: a potent, orally active tachykinin NK(1), NK(2), and NK(3) receptor antagonist.
Eur J Pharmacol, 450 (2): 191-202. [PMID:12206858]
2. Beaujouan JC, Saffroy M, Torrens Y, Glowinski J. (1997)
Potency and selectivity of the tachykinin NK3 receptor antagonist SR 142801.
Eur J Pharmacol, 319 (2-3): 307-16. [PMID:9042606]
3. Chung FZ, Wu LH, Tian Y, Vartanian MA, Lee H, Bikker J, Humblet C, Pritchard MC, Raphy J, Suman-Chauhan N. (1995)
Two classes of structurally different antagonists display similar species preference for the human tachykinin neurokinin3 receptor.
Mol Pharmacol, 48 (4): 711-6. [PMID:7476898]
4. Emonds-Alt X, Bichon D, Ducoux JP, Heaulme M, Miloux B, Poncelet M, Proietto V, Van Broeck D, Vilain P, Neliat G. (1995)
SR 142801, the first potent non-peptide antagonist of the tachykinin NK3 receptor.
Life Sci, 56 (1): PL27-32. [PMID:7830490]
5. Kamali F. (2001)
Osanetant Sanofi-Synthélabo.
Curr Opin Investig Drugs, 2 (7): 950-6. [PMID:11757797]
6. Oury-Donat F, Carayon P, Thurneyssen O, Pailhon V, Emonds-Alt X, Soubrié P, Le Fur G. (1995)
Functional characterization of the nonpeptide neurokinin3 (NK3) receptor antagonist, SR142801 on the human NK3 receptor expressed in Chinese hamster ovary cells.
J Pharmacol Exp Ther, 274 (1): 148-54. [PMID:7616392]
7. Sarau HM, Feild JA, Ames RS, Foley JJ, Nuthulaganti P, Schmidt DB, Buckley PT, Elshourbagy NA, Brawner ME, Luttmann MA et al.. (2001)
Molecular and pharmacological characterization of the murine tachykinin NK(3) receptor.
Eur J Pharmacol, 413 (2-3): 143-50. [PMID:11226387]
8. Sarau HM, Griswold DE, Potts W, Foley JJ, Schmidt DB, Webb EF, Martin LD, Brawner ME, Elshourbagy NA, Medhurst AD et al.. (1997)
Nonpeptide tachykinin receptor antagonists: I. Pharmacological and pharmacokinetic characterization of SB 223412, a novel, potent and selective neurokinin-3 receptor antagonist.
J Pharmacol Exp Ther, 281 (3): 1303-11. [PMID:9190866]
9. Tian Y, Wu LH, Oxender DL, Chung FZ. (1996)
The unpredicted high affinities of a large number of naturally occurring tachykinins for chimeric NK1/NK3 receptors suggest a role for an inhibitory domain in determining receptor specificity.
J Biol Chem, 271 (34): 20250-7. [PMID:8702757]