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sviceucin   Click here for help

GtoPdb Ligand ID: 14264

Synonyms: SSV-2083
Compound class: Peptide
Comment: Sviceucin is an antimicrobial lasso peptide produced by Streptomyces sviceus [2]. Note that the structure shown here matches the CAS-assigned structure.
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@H](C)[C@@]1([H])C(=O)N[C@@H](CSSC[C@@]2([H])C(=O)N[C@@]([H])([C@@H](C)O)C(=O)N[C@@]3([H])CC(=O)N[C@@]([H])(CSSC[C@@]([H])(C(=O)NCC(=O)N[C@@]([H])([C@@H](C)O)C(=O)N[C@@H](C)C(=O)N[C@@H](CC4=CNC5=C4C=CC=C5)C(=O)N1)NC(=O)CNC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC6=CC=CC=C6)NC3=O)C(=O)N[C@@H]([C@H](C)C)C(=O)N[C@@H](CC7=CNC8=C7C=CC=C8)C(=O)NCC(=O)NCC(=O)N[C@@H](CC(=O)O)C(=O)N2)C(=O)N[C@@H](C(C)C)C(=O)O
Isomeric SMILES C(C=1C=2C(NC1)=CC=CC2)[C@H]3C(=O)N[C@@]([C@H](CC)C)(C(=O)N[C@H](C(N[C@@H](C(C)C)C(O)=O)=O)CSSC[C@]4(C(=O)N[C@@]([C@@H](C)O)(C(=O)N[C@@]5(C(=O)N[C@@H](CC6=CC=CC=C6)C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N[C@](C(=O)NCC(=O)N[C@@]([C@@H](C)O)(C(=O)N[C@@H](C)C(=O)N3)[H])(CSSC[C@@](C(=O)N[C@@H]([C@H](C)C)C(=O)N[C@@H](CC=7C=8C(NC7)=CC=CC8)C(=O)NCC(=O)NCC(=O)N[C@@H](CC(O)=O)C(=O)N4)(NC(=O)C5)[H])[H])[H])[H])[H])[H]
InChI InChI=1S/C92H126N22O26S4/c1-12-45(8)74-89(136)109-65(86(133)112-73(44(6)7)92(139)140)41-144-143-40-64-87(134)114-76(48(11)116)91(138)107-60-30-66(117)101-63(85(132)111-72(43(4)5)88(135)106-58(28-50-32-93-54-24-18-16-22-52(50)54)79(126)96-34-67(118)95-35-68(119)100-61(31-71(122)123)83(130)108-64)39-142-141-38-62(102-69(120)36-97-78(125)56(26-42(2)3)104-81(128)57(105-82(60)129)27-49-20-14-13-15-21-49)80(127)98-37-70(121)110-75(47(10)115)90(137)99-46(9)77(124)103-59(84(131)113-74)29-51-33-94-55-25-19-17-23-53(51)55/h13-25,32-33,42-48,56-65,72-76,93-94,115-116H,12,26-31,34-41H2,1-11H3,(H,95,118)(H,96,126)(H,97,125)(H,98,127)(H,99,137)(H,100,119)(H,101,117)(H,102,120)(H,103,124)(H,104,128)(H,105,129)(H,106,135)(H,107,138)(H,108,130)(H,109,136)(H,110,121)(H,111,132)(H,112,133)(H,113,131)(H,114,134)(H,122,123)(H,139,140)/t45-,46-,47+,48+,56-,57-,58-,59-,60-,61-,62-,63-,64-,65-,72-,73-,74-,75-,76-/m0/s1
InChI Key SLPRSALLYDJDLY-CJSAPLTJSA-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. Boudrioua A, Baëtz B, Desmadril S, Goulard C, Groo AC, Lombard C, Gueulle S, Marugan M, Malzert-Fréon A, Hartke A et al.. (2025)
Lasso peptides sviceucin and siamycin I exhibit anti-virulence activity and restore vancomycin effectiveness in vancomycin-resistant pathogens.
iScience, 28 (3): 111922. [PMID:40034853]
2. Li Y, Ducasse R, Zirah S, Blond A, Goulard C, Lescop E, Giraud C, Hartke A, Guittet E, Pernodet JL et al.. (2015)
Characterization of Sviceucin from Streptomyces Provides Insight into Enzyme Exchangeability and Disulfide Bond Formation in Lasso Peptides.
ACS Chem Biol, 10 (11): 2641-9. [PMID:26343290]