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LB10517   Click here for help

GtoPdb Ligand ID: 14441

Synonyms: LK10517
Compound class: Synthetic organic
Comment: LB10517 is a parenteral cephalosporin antibacterial with broad-spectrum activity against Gram-positive and Gram-negative bacteria [2]. Chemically, it is a catechol-conjugated siderophore cephalosporin, a class of antibacterial compounds designed to exploit siderophore-dependent pathways of bacterial iron uptake to improve delivery of antimicrobial agents across the outer membrane of Gram-negative bacteria [1].
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 16
Hydrogen bond donors 8
Rotatable bonds 12
Topological polar surface area 340.51
Molecular weight 683.68
XLogP -2.6
No. Lipinski's rules broken 4

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\C1=C(C(=O)O)N2C(=O)[C@H]([C@H]2SC1)NC(=O)/C(=N/O[C@@H](C3=CC=C(C(=C3)O)O)C(=O)O)/C4=CSC(=N4)N)/CN5C=NC(=CC5=N)N
Isomeric SMILES C1C(=C(N2[C@H](S1)[C@@H](C2=O)NC(=O)/C(=N/O[C@@H](C3=CC(=C(C=C3)O)O)C(=O)O)/C4=CSC(=N4)N)C(=O)O)/C=C/CN5C=NC(=CC5=N)N
InChI InChI=1S/C27H25N9O9S2/c28-16-7-17(29)35(10-31-16)5-1-2-12-8-46-24-19(23(40)36(24)20(12)25(41)42)33-22(39)18(13-9-47-27(30)32-13)34-45-21(26(43)44)11-3-4-14(37)15(38)6-11/h1-4,6-7,9-10,19,21,24,29,37-38H,5,8,28H2,(H2,30,32)(H,33,39)(H,41,42)(H,43,44)/b2-1+,29-17?,34-18+/t19-,21+,24-/m1/s1
InChI Key KIRBXZCFZVFSBG-MOLNTNENSA-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. Curtis NA, Eisenstadt RL, East SJ, Cornford RJ, Walker LA, White AJ. (1988)
Iron-regulated outer membrane proteins of Escherichia coli K-12 and mechanism of action of catechol-substituted cephalosporins.
Antimicrob Agents Chemother, 32 (12): 1879-86. [PMID:3072926]
2. Song HK, Oh JI, Kim MY, Kim YZ, Kim IC, Kwak JH. (1996)
In-vitro and in-vivo antibacterial activity of LB10517, a novel catechol-substituted cephalosporin with a broad antibacterial spectrum.
J Antimicrob Chemother, 37 (4): 711-26. [PMID:8722537]