clobenpropit   Click here for help

GtoPdb Ligand ID: 1223

Synonyms: VUF 9153 | VUF-9153
PDB Ligand Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Clobenpropit (dihydrobromide) is a highly potent H3 receptor antagonist and H4 receptor partial agonist.
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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 Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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 3
Hydrogen bond donors 2
Rotatable bonds 7
Topological polar surface area 92.36
Molecular weight 308.09
XLogP 2.33
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES Clc1ccc(cc1)CN=C(SCCCc1cnc[nH]1)N
Isomeric SMILES Clc1ccc(cc1)CN=C(SCCCc1cnc[nH]1)N
InChI InChI=1S/C14H17ClN4S/c15-12-5-3-11(4-6-12)8-18-14(16)20-7-1-2-13-9-17-10-19-13/h3-6,9-10H,1-2,7-8H2,(H2,16,18)(H,17,19)
InChI Key UCAIEVHKDLMIFL-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
References
1. Buckland KF, Williams TJ, Conroy DM. (2003)
Histamine induces cytoskeletal changes in human eosinophils via the H(4) receptor.
Br J Pharmacol, 140 (6): 1117-27. [PMID:14530216]
2. Chen J, Liu C, Lovenberg TW. (2003)
Molecular and pharmacological characterization of the mouse histamine H3 receptor.
Eur J Pharmacol, 467 (1-3): 57-65. [PMID:12706455]
3. Cogé F, Guénin SP, Audinot V, Renouard-Try A, Beauverger P, Macia C, Ouvry C, Nagel N, Rique H, Boutin JA et al.. (2001)
Genomic organization and characterization of splice variants of the human histamine H3 receptor.
Biochem J, 355 (Pt 2): 279-88. [PMID:11284713]
4. Esbenshade TA, Krueger KM, Miller TR, Kang CH, Denny LI, Witte DG, Yao BB, Fox GB, Faghih R, Bennani YL et al.. (2003)
Two novel and selective nonimidazole histamine H3 receptor antagonists A-304121 and A-317920: I. In vitro pharmacological effects.
J Pharmacol Exp Ther, 305 (3): 887-96. [PMID:12606603]
5. Ligneau X, Morisset S, Tardivel-Lacombe J, Gbahou F, Ganellin CR, Stark H, Schunack W, Schwartz JC, Arrang JM. (2000)
Distinct pharmacology of rat and human histamine H(3) receptors: role of two amino acids in the third transmembrane domain.
Br J Pharmacol, 131 (7): 1247-50. [PMID:11090094]
6. Lim HD, van Rijn RM, Ling P, Bakker RA, Thurmond RL, Leurs R. (2005)
Evaluation of histamine H1-, H2-, and H3-receptor ligands at the human histamine H4 receptor: identification of 4-methylhistamine as the first potent and selective H4 receptor agonist.
J Pharmacol Exp Ther, 314 (3): 1310-21. [PMID:15947036]
7. Liu C, Ma X, Jiang X, Wilson SJ, Hofstra CL, Blevitt J, Pyati J, Li X, Chai W, Carruthers N et al.. (2001)
Cloning and pharmacological characterization of a fourth histamine receptor (H(4)) expressed in bone marrow.
Mol Pharmacol, 59 (3): 420-6. [PMID:11179434]
8. Liu C, Wilson SJ, Kuei C, Lovenberg TW. (2001)
Comparison of human, mouse, rat, and guinea pig histamine H4 receptors reveals substantial pharmacological species variation.
J Pharmacol Exp Ther, 299 (1): 121-30. [PMID:11561071]
9. Lovenberg TW, Pyati J, Chang H, Wilson SJ, Erlander MG. (2000)
Cloning of rat histamine H(3) receptor reveals distinct species pharmacological profiles.
J Pharmacol Exp Ther, 293 (3): 771-8. [PMID:10869375]
10. Morisset S, Sasse A, Gbahou F, Héron A, Ligneau X, Tardivel-Lacombe J, Schwartz JC, Arrang JM. (2001)
The rat H3 receptor: gene organization and multiple isoforms.
Biochem Biophys Res Commun, 280 (1): 75-80. [PMID:11162480]
11. Morse KL, Behan J, Laz TM, West Jr RE, Greenfeder SA, Anthes JC, Umland S, Wan Y, Hipkin RW, Gonsiorek W et al.. (2001)
Cloning and characterization of a novel human histamine receptor.
J Pharmacol Exp Ther, 296 (3): 1058-66. [PMID:11181941]
12. Wieland K, Bongers G, Yamamoto Y, Hashimoto T, Yamatodani A, Menge WM, Timmerman H, Lovenberg TW, Leurs R. (2001)
Constitutive activity of histamine h(3) receptors stably expressed in SK-N-MC cells: display of agonism and inverse agonism by H(3) antagonists.
J Pharmacol Exp Ther, 299 (3): 908-14. [PMID:11714875]
13. Wulff BS, Hastrup S, Rimvall K. (2002)
Characteristics of recombinantly expressed rat and human histamine H3 receptors.
Eur J Pharmacol, 453 (1): 33-41. [PMID:12393057]