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DF3966A   Click here for help

GtoPdb Ligand ID: 12515

Compound class: Synthetic organic
Comment: DF3966A is the (R)-enantiomer of DF3016A [2]. It is small molecular weight C5a1 receptor antagonist [1]. It is able to cross the blood-brain barrier. Chemical name provided in [3].
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 6
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 86.77
Molecular weight 339.32
XLogP 1.14
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 C[C@H](C1=CC=C(C=C1)NC2=NC(=CS2)C(F)(F)F)C3=NN=N[N-]3
Isomeric SMILES FC(C=1N=C(SC1)NC2=CC=C(C=C2)[C@@H](C)C3=NN=N[N-]3)(F)F
InChI InChI=1S/C13H10F3N6S/c1-7(11-19-21-22-20-11)8-2-4-9(5-3-8)17-12-18-10(6-23-12)13(14,15)16/h2-7H,1H3,(H-,17,18,19,20,21,22)/q-1/t7-/m1/s1
InChI Key PAABTMXSERBYBX-SSDOTTSWSA-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. Brandolini L, Grannonico M, Bianchini G, Colanardi A, Sebastiani P, Paladini A, Piroli A, Allegretti M, Varrassi G, Di Loreto S. (2019)
The Novel C5aR Antagonist DF3016A Protects Neurons Against Ischemic Neuroinflammatory Injury.
Neurotox Res, 36 (1): 163-174. [PMID:30953275]
2. Cristiano C, Giorgio C, Cocchiaro P, Boccella S, Cesta MC, Castelli V, Liguori FM, Cuozzo MR, Brandolini L, Russo R et al.. (2023)
Inhibition of C5aR1 as a promising approach to treat taxane-induced neuropathy.
Cytokine, 171: 156370. [PMID:37722320]
3. D'Angelo R, Mangini M, Fonderico J, Fulle S, Mayo E, Aramini A, Mariggiò S. (2020)
Inhibition of osteoclast activity by complement regulation with DF3016A, a novel small-molecular-weight C5aR inhibitor.
Biomed Pharmacother, 123: 109764. [PMID:31901551]