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LFF571   Click here for help

GtoPdb Ligand ID: 14344

Synonyms: J3.333.591A | LFF 571 | LFF-571
Compound class: Peptide
Comment: LFF571 is a macrocyclic thiopetide with activity against Gram-positive bacteria and derived from the naturally occurring antibacterial GE2270 A [2]. Functionally, it inhibits bacterial protein synthesis by targeting elongation factor Tu (EF-Tu) [3]. Note that the structure shown here matches the CAS-assigned structure. The PubChem link, provided in the table below, is to their standardized chemical structure (CID 42638236), although this is not an exact structural match.
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@H]1C2=NC(=C(COC)S2)C(=O)NCC(=O)N[C@@]([H])([C@H](C3=CC=CC=C3)O)C4=NC(=CS4)C5=NC(=CS5)C6=NC(=CC=C6C7=NC(=CS7)C(=O)N[C@@H](CC(=O)NC)C8=NC(=C(C)S8)C(=O)N1)C9=NC(=CS9)N(CCCCC(=O)O)C(=O)O[C@H]%10CC[C@@H](CC%10)C(=O)O
Isomeric SMILES O=C1C=2N=C(C=3C(C=4N=C(SC4)C=5N=C(SC5)[C@]([C@@H](O)C6=CC=CC=C6)(NC(=O)CNC(=O)C7=C(COC)SC([C@H](C(C)C)NC(=O)C=8N=C([C@H](CC(NC)=O)N1)SC8C)=N7)[H])=NC(=CC3)C9=NC(N(C(O[C@@H]%10CC[C@@H](C(O)=O)CC%10)=O)CCCCC(O)=O)=CS9)SC2
InChI InChI=1S/C60H63N13O13S6/c1-28(2)44-58-72-47(39(92-58)23-85-5)51(80)62-22-42(75)69-48(49(78)30-11-7-6-8-12-30)57-67-38(26-89-57)55-65-36(24-88-55)46-33(53-66-37(25-87-53)50(79)64-35(21-41(74)61-4)56-71-45(29(3)91-56)52(81)70-44)18-19-34(63-46)54-68-40(27-90-54)73(20-10-9-13-43(76)77)60(84)86-32-16-14-31(15-17-32)59(82)83/h6-8,11-12,18-19,24-28,31-32,35,44,48-49,78H,9-10,13-17,20-23H2,1-5H3,(H,61,74)(H,62,80)(H,64,79)(H,69,75)(H,70,81)(H,76,77)(H,82,83)/t31-,32-,35-,44-,48-,49-/m0/s1
InChI Key GNLYKLDXQZHYTR-LMOGNUDZSA-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. Bhansali SG, Mullane K, Ting LS, Leeds JA, Dabovic K, Praestgaard J, Pertel P. (2015)
Pharmacokinetics of LFF571 and vancomycin in patients with moderate Clostridium difficile infections.
Antimicrob Agents Chemother, 59 (3): 1441-5. [PMID:25534724]
2. LaMarche MJ, Leeds JA, Amaral A, Brewer JT, Bushell SM, Deng G, Dewhurst JM, Ding J, Dzink-Fox J, Gamber G et al.. (2012)
Discovery of LFF571: an investigational agent for Clostridium difficile infection.
J Med Chem, 55 (5): 2376-87. [PMID:22315981]
3. Leeds JA, Sachdeva M, Mullin S, Dzink-Fox J, Lamarche MJ. (2012)
Mechanism of action of and mechanism of reduced susceptibility to the novel anti-Clostridium difficile compound LFF571.
Antimicrob Agents Chemother, 56 (8): 4463-5. [PMID:22644023]
4. Mullane K, Lee C, Bressler A, Buitrago M, Weiss K, Dabovic K, Praestgaard J, Leeds JA, Blais J, Pertel P. (2015)
Multicenter, randomized clinical trial to compare the safety and efficacy of LFF571 and vancomycin for Clostridium difficile infections.
Antimicrob Agents Chemother, 59 (3): 1435-40. [PMID:25534727]