(3,5)-[19F]2-Phe-ψ-Ala   Click here for help

GtoPdb Ligand ID: 11370

Synonyms: (3,5)-difluoro Phe-ψ-Ala
 Ligand is labelled  Ligand is radioactive
Compound class: Peptide
Comment: A dipeptide probe that can be radiolabelled with the [19F] isotope to study peptide transporters [1]. Alternate probes were tested in this study by Arakawa et al. (2020). The L-phenylalanyl-ψ[CS-N]-L-alanine dipeptide backbone is resistant to cleavage by peptidases.
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 N[C@H](C(=S)NCC(=O)O)Cc1cc([19F])cc(c1)[18F]
Isomeric SMILES N[C@H](C(=S)NCC(=O)O)Cc1cc([19F])cc(c1)[19F]
InChI InChI=1S/C11H12F2N2O2S/c12-7-1-6(2-8(13)4-7)3-9(14)11(18)15-5-10(16)17/h1-2,4,9H,3,5,14H2,(H,15,18)(H,16,17)/t9-/m0/s1/i12-1,13+0
InChI Key TWLHVEKSWVLMAU-DENHMSFDSA-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. Arakawa H, Yamada H, Arai K, Kawanishi T, Nitta N, Shibata S, Matsumoto E, Yano K, Kato Y, Kumamoto T et al.. (2020)
Possible utility of peptide-transporter-targeting [19F]dipeptides for visualization of the biodistribution of cancers by nuclear magnetic resonance imaging.
Int J Pharm, 586: 119575. [PMID:32622809]