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alboverticillin   Click here for help

GtoPdb Ligand ID: 14256

Synonyms: triculamin
Compound class: Peptide
Comment: Alboverticillin is an antimycobacterial compound first isolated from the culture broth of a Streptomyces sp. in the 1950s [2] and recently identified as a lasso peptide [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)N[C@@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCN=C(N)N)C(=O)NCC(=O)O)NC(=O)CNC(=O)[C@@H]1CC(=O)N[C@@H](CO)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCCN)C(=O)N2CCC[C@H]2C(=O)NCC(=O)N1
Isomeric SMILES CC[C@H](C)[C@@H](C(=O)N[C@@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCN=C(N)N)C(=O)NCC(=O)O)NC(=O)CNC(=O)[C@@H]1CC(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N2CCC[C@H]2C(=O)NCC(=O)N1)CCCCN)CO)CCCCN)CCCCN)CO
InChI InChI=1S/C72H129N27O21/c1-5-40(4)58(69(119)94-42(21-14-28-81-71(77)78)60(110)83-32-52(103)88-41(17-6-10-24-73)59(109)84-34-54(105)97-57(39(2)3)68(118)93-43(22-15-29-82-72(79)80)61(111)87-36-56(107)108)98-55(106)35-85-62(112)47-31-51(102)90-48(37-100)65(115)92-44(18-7-11-25-74)63(113)91-45(19-8-12-26-75)64(114)96-49(38-101)66(116)95-46(20-9-13-27-76)70(120)99-30-16-23-50(99)67(117)86-33-53(104)89-47/h39-50,57-58,100-101H,5-38,73-76H2,1-4H3,(H,83,110)(H,84,109)(H,85,112)(H,86,117)(H,87,111)(H,88,103)(H,89,104)(H,90,102)(H,91,113)(H,92,115)(H,93,118)(H,94,119)(H,95,116)(H,96,114)(H,97,105)(H,98,106)(H,107,108)(H4,77,78,81)(H4,79,80,82)/t40-,41-,42-,43-,44-,45-,46-,47-,48-,49-,50-,57-,58-/m0/s1
InChI Key ICDIBSXJAWASKP-HESAYSFXSA-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
Alboverticillin exhibits narrow-spectrum activity against mycobacteria, with an MIC of 0.03-0.06 μg/ml for Mycobacterium phlei and 0.125-0.25 μg/ml for Mycobacterium smegmatis [1].