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lassomycin   Click here for help

GtoPdb Ligand ID: 14265

Compound class: Peptide
Comment: Lassomycin is an antimicrobial lasso peptide, produced by a strain of Lentzea kentuckyensis found in soil, and with potent and selective activity against mycobacteria [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)NC(=O)[C@H](CC(=O)N)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CCCNC(=N)N)NC(=O)CNC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC(=O)N)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](C)NC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CC(C)C)NC(=O)CN
Isomeric SMILES CC[C@H](C)[C@@H](C=O)NC(=O)[C@H](CC(=O)N)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CCCNC(=N)N)NC(=O)CNC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC(=O)N)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](C)NC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CC(C)C)NC(=O)CN
InChI InChI=1S/C82H142N30O20/c1-12-45(10)59(40-113)111-75(129)57(36-61(85)115)110-70(124)51(25-19-31-97-82(92)93)102-67(121)48(22-16-28-94-79(86)87)100-63(117)39-98-78(132)65(44(8)9)112-77(131)55(34-43(6)7)108-71(125)52(26-27-60(84)114)105-76(130)58(37-64(118)119)106-66(120)46(11)99-72(126)56(35-47-20-14-13-15-21-47)109-74(128)54(33-42(4)5)107-69(123)50(24-18-30-96-81(90)91)103-68(122)49(23-17-29-95-80(88)89)104-73(127)53(32-41(2)3)101-62(116)38-83/h13-15,20-21,40-46,48-59,65H,12,16-19,22-39,83H2,1-11H3,(H2,84,114)(H2,85,115)(H,98,132)(H,99,126)(H,100,117)(H,101,116)(H,102,121)(H,103,122)(H,104,127)(H,105,130)(H,106,120)(H,107,123)(H,108,125)(H,109,128)(H,110,124)(H,111,129)(H,112,131)(H,118,119)(H4,86,87,94)(H4,88,89,95)(H4,90,91,96)(H4,92,93,97)/t45-,46-,48-,49-,50-,51-,52-,53-,54-,55-,56-,57-,58-,59+,65-/m0/s1
InChI Key NLWVIEFILMVVQV-OBXQOZEMSA-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. Gavrish E, Sit CS, Cao S, Kandror O, Spoering A, Peoples A, Ling L, Fetterman A, Hughes D, Bissell A et al.. (2014)
Lassomycin, a ribosomally synthesized cyclic peptide, kills mycobacterium tuberculosis by targeting the ATP-dependent protease ClpC1P1P2.
Chem Biol, 21 (4): 509-518. [PMID:24684906]