colistin   Click here for help

GtoPdb Ligand ID: 10794

Synonyms: Colobreathe® | polymyxin E | Promixin®
Approved drug
colistin is an approved drug (UK (2006))
Compound class: Natural product
Comment: Colistin is a cyclic polypeptide (IUPAC condensed sequence Unk-Dab-Thr-Dab-Dab(1)-Dab-D-Leu-Leu-Dab-Dab-Thr-(1)) antibacterial from Bacillus colistinus. It contains Polymyxins E1 and E2 and acts as a detergent on cell membranes.
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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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were 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/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 29
Hydrogen bond donors 18
Rotatable bonds 32
Topological polar surface area 490.66
Molecular weight 1154.75
XLogP 0.63
No. Lipinski's rules broken 3

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/)
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)CC(C)C)CC(C)C)CCN)[C@H](O)C)NC(=O)[C@H]([C@H](O)C)NC(=O)[C@@H](NC(=O)CCCC(CC)C)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)CC(C)C)CC(C)C)CCN)[C@H](O)C)NC(=O)[C@H]([C@H](O)C)NC(=O)[C@@H](NC(=O)CCCC(CC)C)CCN
InChI InChI=1S/C52H98N16O13/c1-9-29(6)11-10-12-40(71)59-32(13-19-53)47(76)68-42(31(8)70)52(81)64-35(16-22-56)44(73)63-37-18-24-58-51(80)41(30(7)69)67-48(77)36(17-23-57)61-43(72)33(14-20-54)62-49(78)38(25-27(2)3)66-50(79)39(26-28(4)5)65-45(74)34(15-21-55)60-46(37)75/h27-39,41-42,69-70H,9-26,53-57H2,1-8H3,(H,58,80)(H,59,71)(H,60,75)(H,61,72)(H,62,78)(H,63,73)(H,64,81)(H,65,74)(H,66,79)(H,67,77)(H,68,76)/t29?,30-,31-,32+,33+,34+,35+,36+,37+,38+,39-,41+,42+/m1/s1
InChI Key YKQOSKADJPQZHB-QNPLFGSASA-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/)
Targets where the ligand is described in the comment field
Target Comment
Peptide transporter 2 Although most di/tripeptides can bind PEPT2, not all of them are substrates. The uptake depends on the structural features (charge, hydrophobicity, size, side chain flexibility, etc.) of the di/tripeptide. Like PEPT1, PEPT2 interacts with dipeptides and drugs including D-Phe-Ala [2,8], nateglinide [7], glibenclamide [6], penicillin G (benzylpenicillin) [5], polymyxins (i.e. polymyxin B and colistin) [3] and entecavir [9]. PEPT2 has been shown to interact with dipeptides of p-borono-L-phenylalanine (BPA) and tyrosine (i.e. L-Tyr-p-L-BPA (Tyr-BPA), p-L-BPA-L-tyrosine (BPA-Tyr)) [4] and with AuIII‐peptidodithiocarbamato complexes of the type [AuIIIBr2(dtc‐AA1‐AA2‐OR), in which AA1 = N‐methylglycine (Sar), L/D‐Pro; AA2 = L/D‐Ala, α‐aminoisobutyric acid (Aib); R = OtBu, triethylene glycol methyl ether, e.g. dtc‐Pro‐Aib‐OtBu) [1].