RS-102895   Click here for help

GtoPdb Ligand ID: 779

Synonyms: abaucin | RS102895
PDB Ligand Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: RS-102895 is a CCR2b antagonist [1,3]. The endogenous ligand for this GPCR is monocyte chemoattracant-1 (MCP-1), which stimulates leukocyte chemotaxis to inflammatory sites.
In the search for new antibacterials with activity against Acinetobacter baumannii (a nosocomial Gram-negative pathogen that often displays multidrug resistance), artificial intelligence (AI) algorithms were used to identify novel chemotypes. RS-102895 (renamed as abaucin) was identified using this approach, with narrow-spectrum in vitro and in vivo activity against A. baumannii [2].
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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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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 4
Hydrogen bond donors 1
Rotatable bonds 4
Topological polar surface area 41.57
Molecular weight 390.16
XLogP 4.08
No. Lipinski's rules broken 0
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=C1Nc2ccccc2C2(O1)CCN(CC2)CCc1ccc(cc1)C(F)(F)F
Isomeric SMILES O=C1Nc2ccccc2C2(O1)CCN(CC2)CCc1ccc(cc1)C(F)(F)F
InChI InChI=1S/C21H21F3N2O2/c22-21(23,24)16-7-5-15(6-8-16)9-12-26-13-10-20(11-14-26)17-3-1-2-4-18(17)25-19(27)28-20/h1-8H,9-14H2,(H,25,27)
InChI Key HIDWEYPGMLIQSN-UHFFFAOYSA-N
References
1. Clark RD, Caroon JM, Kluge AF, Repke DB, Roszkowski AP, Strosberg AM, Baker S, Bitter SM, Okada MD. (1983)
Synthesis and antihypertensive activity of 4'-substituted spiro[4H-3,1-benzoxazine-4,4'-piperidin]-2(1H)-ones.
J Med Chem, 26 (5): 657-61. [PMID:6842505]
2. Liu G, Catacutan DB, Rathod K, Swanson K, Jin W, Mohammed JC, Chiappino-Pepe A, Syed SA, Fragis M, Rachwalski K et al.. (2023)
Deep learning-guided discovery of an antibiotic targeting Acinetobacter baumannii.
Nat Chem Biol, 19 (11): 1342-1350. [PMID:37231267]
3. Mirzadegan T, Diehl F, Ebi B, Bhakta S, Polsky I, McCarley D, Mulkins M, Weatherhead GS, Lapierre JM, Dankwardt J et al.. (2000)
Identification of the binding site for a novel class of CCR2b chemokine receptor antagonists: binding to a common chemokine receptor motif within the helical bundle.
J Biol Chem, 275 (33): 25562-71. [PMID:10770925]