MX-2401   Click here for help

GtoPdb Ligand ID: 13518

Compound class: Synthetic organic
Comment: MX-2401 is a lipopeptide antibacterial compound and a semisynthetic analogue of the natural product amphomycin [2].
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 37
Hydrogen bond donors 17
Rotatable bonds 32
Topological polar surface area 565.04
Molecular weight 1468.61
XLogP 2.51
No. Lipinski's rules broken 4

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 CCCCCCCCCCCC(=O)NC1=CC=C(C=C1)C(=O)NC(CC(=O)O)C(=O)NC2C(C)NC(=O)C3([H])CCCN3C(=O)C(C(C)C)NC(=O)C(C(C)NC(=O)CCN)NC(=O)CNC(=O)C(CC(=O)O)NC(=O)CNC(=O)C(CC(=O)O)NC(=O)C(C(C)C(=O)O)NC(=O)C4([H])CCCCN4C2=O
Isomeric SMILES O=C1N2C(C(=O)NC(C(C(O)=O)C)C(=O)NC(CC(O)=O)C(=O)NCC(=O)NC(CC(O)=O)C(=O)NCC(=O)NC(C(NC(CCN)=O)C)C(=O)NC(C(C)C)C(=O)N3C(C(=O)NC(C)C1NC(C(NC(=O)C4=CC=C(NC(CCCCCCCCCCC)=O)C=C4)CC(O)=O)=O)(CCC3)[H])(CCCC2)[H]
InChI InChI=1S/C67H101N15O22/c1-7-8-9-10-11-12-13-14-15-21-46(83)73-40-24-22-39(23-25-40)57(93)75-43(32-52(91)92)60(96)80-56-38(6)72-61(97)45-20-18-29-82(45)65(101)53(35(2)3)78-64(100)55(37(5)71-47(84)26-27-68)77-49(86)34-70-58(94)41(30-50(87)88)74-48(85)33-69-59(95)42(31-51(89)90)76-63(99)54(36(4)67(103)104)79-62(98)44-19-16-17-28-81(44)66(56)102/h22-25,35-38,41-45,53-56H,7-21,26-34,68H2,1-6H3,(H,69,95)(H,70,94)(H,71,84)(H,72,97)(H,73,83)(H,74,85)(H,75,93)(H,76,99)(H,77,86)(H,78,100)(H,79,98)(H,80,96)(H,87,88)(H,89,90)(H,91,92)(H,103,104)
InChI Key FVWLJHLXFKFMJA-UHFFFAOYSA-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. Dugourd D, Yang H, Elliott M, Siu R, Clement JJ, Straus SK, Hancock RE, Rubinchik E. (2011)
Antimicrobial properties of MX-2401, an expanded-spectrum lipopeptide active in the presence of lung surfactant.
Antimicrob Agents Chemother, 55 (8): 3720-8. [PMID:21576435]
2. Pasetka CJ, Erfle DJ, Cameron DR, Clement JJ, Rubinchik E. (2010)
Novel antimicrobial lipopeptides with long in vivo half-lives.
Int J Antimicrob Agents, 35 (2): 182-5. [PMID:20006467]
3. Rubinchik E, Schneider T, Elliott M, Scott WR, Pan J, Anklin C, Yang H, Dugourd D, Müller A, Gries K et al.. (2011)
Mechanism of action and limited cross-resistance of new lipopeptide MX-2401.
Antimicrob Agents Chemother, 55 (6): 2743-54. [PMID:21464247]