NAB739   Click here for help

GtoPdb Ligand ID: 13588

Compound class: Peptide
Comment: NAB739 is from a series of polymyxin B analogues, designed to address the need for new antibacterial compounds with activity against multidrug-resistant (MDR) Gram-negative bacteria [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 CCCCCCCC(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CO)C(=O)NC1CCNC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCN)NC(=O)[C@H](CCN)NC(=O)C(CC(C)C)NC(=O)[C@@H](CC2=CC=CC=C2)NC(=O)[C@H](CCN)NC1=O
Isomeric SMILES CCCCCCCC(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CO)C(=O)NC1CCNC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)C(NC(=O)[C@H](NC(=O)[C@@H](NC1=O)CCN)CC2=CC=CC=C2)CC(C)C)CCN)CCN)[C@@H](C)O
InChI InChI=1S/C50H85N13O13/c1-6-7-8-9-13-16-39(67)62-41(30(5)66)50(76)61-38(27-64)48(74)58-35-20-24-54-49(75)40(29(4)65)63-45(71)34(19-23-53)56-42(68)32(17-21-51)57-46(72)36(25-28(2)3)59-47(73)37(26-31-14-11-10-12-15-31)60-43(69)33(18-22-52)55-44(35)70/h10-12,14-15,28-30,32-38,40-41,64-66H,6-9,13,16-27,51-53H2,1-5H3,(H,54,75)(H,55,70)(H,56,68)(H,57,72)(H,58,74)(H,59,73)(H,60,69)(H,61,76)(H,62,67)(H,63,71)/t29-,30-,32+,33+,34+,35?,36?,37-,38+,40+,41+/m1/s1
InChI Key MDZVFKKBSGQKQR-XNUGQAHBSA-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. Vaara M, Fox J, Loidl G, Siikanen O, Apajalahti J, Hansen F, Frimodt-Møller N, Nagai J, Takano M, Vaara T. (2008)
Novel polymyxin derivatives carrying only three positive charges are effective antibacterial agents.
Antimicrob Agents Chemother, 52 (9): 3229-36. [PMID:18591267]
2. Vaara M, Sader HS, Rhomberg PR, Jones RN, Vaara T. (2013)
Antimicrobial activity of the novel polymyxin derivative NAB739 tested against Gram-negative pathogens.
J Antimicrob Chemother, 68 (3): 636-9. [PMID:23134658]
3. Vaara M, Vaara T, Vingsbo Lundberg C. (2018)
Polymyxin derivatives NAB739 and NAB815 are more effective than polymyxin B in murine Escherichia coli pyelonephritis.
J Antimicrob Chemother, 73 (2): 452-455. [PMID:29149329]