CB-182804   Click here for help

GtoPdb Ligand ID: 11003

Synonyms: CB-182,804 | CB182804
Compound class: Peptide
Comment: CB-182804 is a polymyxin B analogue with antibacterial activity against Gram-positive clinical isolates [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 NCC[C@@H](C(=O)N[C@H]1CCNC(=O)[C@@H](NC(=O)[C@H](CCN)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC1=O)CCN)Cc1ccccc1)CC(C)C)CCN)[C@H](O)C)NC(=O)[C@H]([C@H](O)C)NC(=O)[C@@H](NC(=O)Nc1ccccc1Cl)CCN
Isomeric SMILES NCC[C@@H](C(=O)N[C@H]1CCNC(=O)[C@@H](NC(=O)[C@H](CCN)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC1=O)CCN)Cc1ccccc1)CC(C)C)CCN)[C@H](O)C)NC(=O)[C@H]([C@H](O)C)NC(=O)[C@@H](NC(=O)Nc1ccccc1Cl)CCN
InChI InChI=1S/C54H86ClN17O13/c1-28(2)26-40-50(81)64-34(14-20-56)44(75)63-37(17-23-59)48(79)71-42(29(3)73)52(83)61-25-19-39(47(78)62-35(15-21-57)46(77)68-41(51(82)67-40)27-31-10-6-5-7-11-31)65-45(76)36(16-22-58)66-53(84)43(30(4)74)72-49(80)38(18-24-60)70-54(85)69-33-13-9-8-12-32(33)55/h5-13,28-30,34-43,73-74H,14-27,56-60H2,1-4H3,(H,61,83)(H,62,78)(H,63,75)(H,64,81)(H,65,76)(H,66,84)(H,67,82)(H,68,77)(H,71,79)(H,72,80)(H2,69,70,85)/t29-,30-,34+,35+,36+,37+,38+,39+,40+,41+,42+,43+/m1/s1
InChI Key OINMSSZOBLWDTB-SHGLBBHXSA-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
In in vitro assays the MICs of CB-182804 were generally two-fold higher than those for polymyxin B [1].