neoceptin-4   Click here for help

GtoPdb Ligand ID: 9138

Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Neoceptin-4 is a synthetic Toll-like receptor 4 (TLR4) agonist [2]. It bears no structural similarity with the endogenous ligand for TLR4, LPS. This is one of the compounds claimed in patent WO2014131023 [1] in which the neoceptin's action as an immune system adjuvant is claimed. Neoceptins are claimed for their ability to elicit an immune response via the TLR4, without the toxicity exhibited by LPS.
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 110.88
Molecular weight 476.23
XLogP 5.16
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)OCc1ccc(cc1)O)N)CCc1ccccc1)OC(C)(C)C
Isomeric SMILES O=C([C@H](NC(=O)c1ccc(c(c1)OCc1ccc(cc1)O)N)CCc1ccccc1)OC(C)(C)C
InChI InChI=1S/C28H32N2O5/c1-28(2,3)35-27(33)24(16-11-19-7-5-4-6-8-19)30-26(32)21-12-15-23(29)25(17-21)34-18-20-9-13-22(31)14-10-20/h4-10,12-15,17,24,31H,11,16,18,29H2,1-3H3,(H,30,32)/t24-/m1/s1
InChI Key NRHPXDROGIVILZ-XMMPIXPASA-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/)
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
tert-butyl (2R)-2-({4-amino-3-[(4-hydroxyphenyl)methoxy]phenyl}formamido)-4-phenylbutanoate
Database Links Click here for help
GtoPdb PubChem SID 315661223
PubChem CID 121231399
Search Google for chemical match using the InChIKey NRHPXDROGIVILZ-XMMPIXPASA-N
Search Google for chemicals with the same backbone NRHPXDROGIVILZ
UniChem Compound Search for chemical match using the InChIKey NRHPXDROGIVILZ-XMMPIXPASA-N
UniChem Connectivity Search for chemical match using the InChIKey NRHPXDROGIVILZ-XMMPIXPASA-N