SPR741   Click here for help

GtoPdb Ligand ID: 13250

Synonyms: NAB741
Compound class: Peptide
Comment: SPR741 is a cationic peptide derived from polymyxin B. It is a potentiator molecule that acts by increasing the permeability of the outer membrane of Gram-negative bacteria [3]. It was designed to extend the spectrum and enhance the potency of existing antibacterial compounds and for use in combination therapies to treat severe infections caused by Gram-negative bacteria.
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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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 CC(C)C[C@H]1C(=O)N[C@@H](CCN)C(=O)N[C@@H](CCN)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC[C@@H](C(=O)N[C@@H](CCN)C(=O)N[C@H](CC2=CC=CC=C2)C(=O)N1)NC(=O)[C@@H](CO)NC(=O)[C@H]([C@@H](C)O)NC(=O)C
Isomeric SMILES C[C@H]([C@H]1C(=O)NCC[C@@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N1)CCN)CCN)CC(C)C)CC2=CC=CC=C2)CCN)NC(=O)[C@@H](CO)NC(=O)[C@H]([C@@H](C)O)NC(=O)C)O
InChI InChI=1S/C44H73N13O13/c1-22(2)19-31-40(66)52-27(11-15-45)36(62)51-29(13-17-47)39(65)57-34(23(3)59)43(69)48-18-14-30(53-42(68)33(21-58)56-44(70)35(24(4)60)49-25(5)61)38(64)50-28(12-16-46)37(63)55-32(41(67)54-31)20-26-9-7-6-8-10-26/h6-10,22-24,27-35,58-60H,11-21,45-47H2,1-5H3,(H,48,69)(H,49,61)(H,50,64)(H,51,62)(H,52,66)(H,53,68)(H,54,67)(H,55,63)(H,56,70)(H,57,65)/t23-,24-,27+,28+,29+,30+,31+,32-,33-,34+,35+/m1/s1
InChI Key JBFNEVNUGGFPBQ-DDMCRLCFSA-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. Butler MS, Henderson IR, Capon RJ, Blaskovich MAT. (2023)
Antibiotics in the clinical pipeline as of December 2022.
J Antibiot (Tokyo), 76 (8): 431-473. [PMID:37291465]
2. Corbett D, Wise A, Langley T, Skinner K, Trimby E, Birchall S, Dorali A, Sandiford S, Williams J, Warn P et al.. (2017)
Potentiation of Antibiotic Activity by a Novel Cationic Peptide: Potency and Spectrum of Activity of SPR741.
Antimicrob Agents Chemother, 61 (8). [PMID:28533232]
3. Vaara M, Siikanen O, Apajalahti J, Fox J, Frimodt-Møller N, He H, Poudyal A, Li J, Nation RL, Vaara T. (2010)
A novel polymyxin derivative that lacks the fatty acid tail and carries only three positive charges has strong synergism with agents excluded by the intact outer membrane.
Antimicrob Agents Chemother, 54 (8): 3341-6. [PMID:20479195]