AZD8848   Click here for help

GtoPdb Ligand ID: 9256

Synonyms: DSP-3025
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: AZD8848 is an investigational agonist, selective for Toll-like receptor 7 (TLR7) [2]. It is Example 2-37 claimed in patent US20140045837 [5].
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 9
Hydrogen bond donors 2
Rotatable bonds 17
Topological polar surface area 140.83
Molecular weight 569.33
XLogP 2.42
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 CCCCOc1nc(N)c2c(n1)n(CCCN(Cc1cccc(c1)CC(=O)OC)CCCN1CCOCC1)c(=O)[nH]2
Isomeric SMILES CCCCOc1nc(N)c2c(n1)n(CCCN(Cc1cccc(c1)CC(=O)OC)CCCN1CCOCC1)c(=O)[nH]2
InChI InChI=1S/C29H43N7O5/c1-3-4-16-41-28-32-26(30)25-27(33-28)36(29(38)31-25)13-7-12-35(11-6-10-34-14-17-40-18-15-34)21-23-9-5-8-22(19-23)20-24(37)39-2/h5,8-9,19H,3-4,6-7,10-18,20-21H2,1-2H3,(H,31,38)(H2,30,32,33)
InChI Key FEFIBEHSXLKJGI-UHFFFAOYSA-N
References
1. Aryan Z, Rezaei N. (2015)
Toll-like receptors as targets for allergen immunotherapy.
Curr Opin Allergy Clin Immunol, 15 (6): 568-74. [PMID:26418475]
2. Biggadike K, Ahmed M, Ball DI, Coe DM, Dalmas Wilk DA, Edwards CD, Gibbon BH, Hardy CJ, Hermitage SA, Hessey JO et al.. (2016)
Discovery of 6-Amino-2-{[(1S)-1-methylbutyl]oxy}-9-[5-(1-piperidinyl)pentyl]-7,9-dihydro-8H-purin-8-one (GSK2245035), a Highly Potent and Selective Intranasal Toll-Like Receptor 7 Agonist for the Treatment of Asthma.
J Med Chem, 59 (5): 1711-26. [PMID:26861551]
3. Greiff L, Ahlström-Emanuelsson C, Alenäs M, Almqvist G, Andersson M, Cervin A, Dolata J, Lindgren S, Mårtensson A, Young B et al.. (2015)
Biological effects and clinical efficacy of a topical Toll-like receptor 7 agonist in seasonal allergic rhinitis: a parallel group controlled phase IIa study.
Inflamm Res, 64 (11): 903-15. [PMID:26342289]
4. Greiff L, Cervin A, Ahlström-Emanuelsson C, Almqvist G, Andersson M, Dolata J, Eriksson L, Högestätt E, Källén A, Norlén P et al.. (2012)
Repeated intranasal TLR7 stimulation reduces allergen responsiveness in allergic rhinitis.
Respir Res, 13: 53. [PMID:22726593]
5. Kurimoto A, Hashimoto K, Isobe Y, Brough S, Millichip I, Wada H, Bonnert R, McInally T. (2014)
9-Substituted 8-Oxoadenine Compound.
Patent number: US20140045837. Assignee: Astrazeneca Aktiebolag, Dainippon Sumitomo Pharma Co., Ltd.. Priority date: 26/03/2004. Publication date: 13/02/2014.