alafosfalin   Click here for help

GtoPdb Ligand ID: 9503

Synonyms: alaphosphin
PDB Ligand
Compound class: Peptide
Comment: Alafosfalin is a phosphonodipeptide with antibacterial and antifungal properties [1].

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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(P(=O)(O)O)NC(=O)C(N)C
Isomeric SMILES C[C@@H](P(=O)(O)O)NC(=O)[C@@H](N)C
InChI InChI=1S/C5H13N2O4P/c1-3(6)5(8)7-4(2)12(9,10)11/h3-4H,6H2,1-2H3,(H,7,8)(H2,9,10,11)/t3-,4+/m0/s1
InChI Key BHAYDBSYOBONRV-IUYQGCFVSA-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. Allen JG, Atherton FR, Hall MJ, Hassall CH, Holmes SW, Lambert RW, Nisbet LJ, Ringrose PS. (1979)
Phosphonopeptides as antibacterial agents: alaphosphin and related phosphonopeptides.
Antimicrob Agents Chemother, 15 (5): 684-95. [PMID:43113]
2. Neumann J, Bruch M, Gebauer S, Brandsch M. (2004)
Transport of the phosphonodipeptide alafosfalin by the H+/peptide cotransporters PEPT1 and PEPT2 in intestinal and renal epithelial cells.
Eur J Biochem, 271 (10): 2012-7. [PMID:15128310]