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surotomycin   Click here for help

GtoPdb Ligand ID: 14281

Synonyms: CB-183,315 | MK-4261
Compound class: Peptide
Comment: Surotomycin is a cyclic lipopeptide analogue of daptomycin. It has activity against Gram-positive bacteria, including Clostridium difficile, but limited activity against Gram-negative pathogens [3,5].
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 CCCCCC1=CC=C(C=C1)/C(=C/C(=O)N[C@@H](CC2=CNC3=C2C=CC=C3)C(=O)N[C@H](CC(=O)N)C(=O)N[C@@H](CC(=O)O)C(=O)N[C@H]4[C@@H](C)OC(=O)[C@H](CC(=O)C5=C(C=CC=C5)N)NC(=O)[C@H]([C@H](C)CC(=O)O)NC(=O)[C@@H](CO)NC(=O)CNC(=O)[C@H](CC(=O)O)NC(=O)[C@@H](C)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](CCCN)NC(=O)CNC4=O)/C
Isomeric SMILES CCCCCC1=CC=C(C=C1)/C(=C/C(=O)N[C@@H](CC2=CNC3=CC=CC=C32)C(=O)N[C@H](CC(=O)N)C(=O)N[C@@H](CC(=O)O)C(=O)N[C@H]4[C@H](OC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](NC(=O)CNC(=O)[C@@H](NC(=O)[C@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)CNC4=O)CCCN)CC(=O)O)C)CC(=O)O)CO)[C@H](C)CC(=O)O)CC(=O)C5=CC=CC=C5N)C)/C
InChI InChI=1S/C77H101N17O26/c1-6-7-8-14-41-20-22-42(23-21-41)37(2)25-58(98)86-49(27-43-33-81-47-18-12-10-15-44(43)47)71(113)89-50(29-57(80)97)72(114)91-53(32-64(107)108)73(115)94-66-40(5)120-77(119)54(28-56(96)45-16-9-11-17-46(45)79)92-76(118)65(38(3)26-61(101)102)93-74(116)55(36-95)87-60(100)34-82-68(110)51(30-62(103)104)88-67(109)39(4)84-70(112)52(31-63(105)106)90-69(111)48(19-13-24-78)85-59(99)35-83-75(66)117/h9-12,15-18,20-23,25,33,38-40,48-55,65-66,81,95H,6-8,13-14,19,24,26-32,34-36,78-79H2,1-5H3,(H2,80,97)(H,82,110)(H,83,117)(H,84,112)(H,85,99)(H,86,98)(H,87,100)(H,88,109)(H,89,113)(H,90,111)(H,91,114)(H,92,118)(H,93,116)(H,94,115)(H,101,102)(H,103,104)(H,105,106)(H,107,108)/b37-25+/t38-,39-,40-,48+,49+,50-,51+,52+,53+,54+,55-,65+,66+/m1/s1
InChI Key DYNMYYRPPFVAKR-CWXHRMTKSA-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. Alam MZ, Wu X, Mascio C, Chesnel L, Hurdle JG. (2015)
Mode of action and bactericidal properties of surotomycin against growing and nongrowing Clostridium difficile.
Antimicrob Agents Chemother, 59 (9): 5165-70. [PMID:26055381]
2. Boix V, Fedorak RN, Mullane KM, Pesant Y, Stoutenburgh U, Jin M, Adedoyin A, Chesnel L, Guris D, Larson KB et al.. (2017)
Primary Outcomes From a Phase 3, Randomized, Double-Blind, Active-Controlled Trial of Surotomycin in Subjects With Clostridium difficile Infection.
Open Forum Infect Dis, 4 (1): ofw275. [PMID:28480267]
3. Citron DM, Tyrrell KL, Merriam CV, Goldstein EJ. (2012)
In vitro activities of CB-183,315, vancomycin, and metronidazole against 556 strains of Clostridium difficile, 445 other intestinal anaerobes, and 56 Enterobacteriaceae species.
Antimicrob Agents Chemother, 56 (3): 1613-5. [PMID:22183166]
4. Daley P, Louie T, Lutz JE, Khanna S, Stoutenburgh U, Jin M, Adedoyin A, Chesnel L, Guris D, Larson KB et al.. (2017)
Surotomycin versus vancomycin in adults with Clostridium difficile infection: primary clinical outcomes from the second pivotal, randomized, double-blind, Phase 3 trial.
J Antimicrob Chemother, 72 (12): 3462-3470. [PMID:28961905]
5. Snydman DR, Jacobus NV, McDermott LA. (2012)
Activity of a novel cyclic lipopeptide, CB-183,315, against resistant Clostridium difficile and other Gram-positive aerobic and anaerobic intestinal pathogens.
Antimicrob Agents Chemother, 56 (6): 3448-52. [PMID:22391542]