GtoPdb is requesting financial support from commercial users. Please see our sustainability page for more information.

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
Click here for help

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.

✖
Click here for structure editor
SMILES / InChI / InChIKey
Click here for help

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/)

✖
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/)
Bioactivity Comments
Although sviceucin displays only weak intrinsic Gram-positive antibacterial activity, it restores susceptibility to vancomycin in VanB-expressing strains and has antivirulence properties against pathogenic enterococci [1].