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citrocin   Click here for help

GtoPdb Ligand ID: 14236

Compound class: Peptide
Comment: Citrocin is an antimicrobial lasso peptide discovered using genome mining from Citrobacter pasteurii and Citrobacter braakii [1].
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@@H](C(=O)NCC(=O)NCC(=O)NCC(=O)N[C@@H](C(C)C)C(=O)NCC(=O)N[C@@H](CCNC(=N)N)C(=O)N[C@@H](CC1=CC=C(C=C1)O)C(=O)NCC(=O)O)NC(=O)[C@H](CC2=CC=CC=C2)NC(=O)[C@H](CC3=CC=C(C=C3)O)NC(=O)[C@@H]4CCC(=O)NCC(=O)NCC(=O)N[C@@H](C(C)C)C(=O)NCC(=O)NC(CCCCCN)C(=O)NC([C@H](C)CC)C(=O)N[C@@H](C(C)CC)C(=O)N4
Isomeric SMILES CC[C@@H](C)C1C(=O)N[C@H](C(=O)N[C@@H](CCC(=O)NCC(=O)NCC(=O)N[C@H](C(=O)NCC(=O)NC(C(=O)N1)CCCCCN)C(C)C)C(=O)N[C@@H](CC2=CC=C(C=C2)O)C(=O)N[C@@H](CC3=CC=CC=C3)C(=O)N[C@@H]([C@H](C)CC)C(=O)NCC(=O)NCC(=O)NCC(=O)N[C@@H](C(C)C)C(=O)NCC(=O)N[C@@H](CCNC(=N)N)C(=O)N[C@@H](CC4=CC=C(C=C4)O)C(=O)NCC(=O)O)C(C)CC
InChI InChI=1S/C88H133N23O23/c1-11-49(8)74(85(132)97-41-66(117)94-40-65(116)96-43-70(121)108-73(48(6)7)84(131)99-45-68(119)102-59(33-35-92-88(90)91)79(126)104-60(77(124)100-46-71(122)123)37-53-23-27-55(112)28-24-53)109-82(129)62(36-52-20-16-14-17-21-52)106-81(128)61(38-54-25-29-56(113)30-26-54)105-78(125)58-31-32-63(114)93-39-64(115)95-42-69(120)107-72(47(4)5)83(130)98-44-67(118)101-57(22-18-15-19-34-89)80(127)110-76(51(10)13-3)87(134)111-75(50(9)12-2)86(133)103-58/h14,16-17,20-21,23-30,47-51,57-62,72-76,112-113H,11-13,15,18-19,22,31-46,89H2,1-10H3,(H,93,114)(H,94,117)(H,95,115)(H,96,116)(H,97,132)(H,98,130)(H,99,131)(H,100,124)(H,101,118)(H,102,119)(H,103,133)(H,104,126)(H,105,125)(H,106,128)(H,107,120)(H,108,121)(H,109,129)(H,110,127)(H,111,134)(H,122,123)(H4,90,91,92)/t49-,50?,51-,57?,58+,59+,60+,61+,62+,72+,73+,74+,75+,76?/m1/s1
InChI Key CNUGGUJSKKNENX-NCROSIFOSA-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. Cheung-Lee WL, Parry ME, Jaramillo Cartagena A, Darst SA, Link AJ. (2019)
Discovery and structure of the antimicrobial lasso peptide citrocin.
J Biol Chem, 294 (17): 6822-6830. [PMID:30846564]