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neoceptin-3   Click here for help

GtoPdb Ligand ID: 9137

PDB Ligand Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Neoceptin-3 is a synthetic molecular Toll-like receptor 4 (TLR4) agonist mimetic [2]. It bears no structural similarity with the endogenous ligand for TLR4, LPS, and in fact the biologically relevant molecular target for neoseptin-3 is the TLR4/MD-2 (LY96) complex [3]. This is one of the compounds claimed in patent WO2014131023 [1] in which the compound's action as an immune system adjuvant is claimed. Neoceptin-3 is claimed for its ability to elicit an immune response via TLR4, without the toxicity exhibited by LPS [3]. The S stereoisomer is specified in [3]. The R stereoisomer is represented by PubChem CID 90371379.

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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 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 5
Hydrogen bond donors 3
Rotatable bonds 12
Topological polar surface area 101.65
Molecular weight 474.25
XLogP 5.67
No. Lipinski's rules broken 2

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 O=C(C(NC(=O)c1ccc(c(c1)CCc1ccc(cc1)O)N)CCc1ccccc1)OC(C)(C)C
Isomeric SMILES O=C([C@@H](NC(=O)c1ccc(c(c1)CCc1ccc(cc1)O)N)CCc1ccccc1)OC(C)(C)C
InChI InChI=1S/C29H34N2O4/c1-29(2,3)35-28(34)26(18-12-20-7-5-4-6-8-20)31-27(33)23-14-17-25(30)22(19-23)13-9-21-10-15-24(32)16-11-21/h4-8,10-11,14-17,19,26,32H,9,12-13,18,30H2,1-3H3,(H,31,33)/t26-/m0/s1
InChI Key OACODUCFPHHCIH-SANMLTNESA-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. Beutler B, Boger DL. (2014)
Neoseptins: small molecule adjuvants.
Patent number: WO2014131023 A1. Assignee: The Scripps Research Institute, The Board Of Regents Of The University Of Texas System. Priority date: 25/02/2013. Publication date: 28/08/2014.
2. Morin MD, Wang Y, Jones BT, Su L, Surakattula MM, Berger M, Huang H, Beutler EK, Zhang H, Beutler B et al.. (2016)
Discovery and Structure-Activity Relationships of the Neoseptins: A New Class of Toll-like Receptor-4 (TLR4) Agonists.
J Med Chem, 59 (10): 4812-30. [PMID:27050713]
3. Wang Y, Su L, Morin MD, Jones BT, Whitby LR, Surakattula MM, Huang H, Shi H, Choi JH, Wang KW et al.. (2016)
TLR4/MD-2 activation by a synthetic agonist with no similarity to LPS.
Proc Natl Acad Sci USA, 113 (7): E884-93. [PMID:26831104]
4. (2011)
SECTION II: NEUROPHARMACOLOGY.  In  Goodman and Gilman's The Pharmacological Basis of Therapeutics, Twelfth Edition
Edited by Brunton L, Chabner B, Knollman B (McGraw-Hill Professional) 1808. [ISBN:9780071624428]