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aspartame   Click here for help

GtoPdb Ligand ID: 13899

Synonyms: Canderel® | NutraSweet® | SC18862
PDB Ligand
Compound class: Peptide
Comment: Aspartame is a widely utilised artificial sweetner. Structurally is is a aspartylphenylalanine methyl ester. Cryo-EM analysis has determined that aspartame binds to the Venus flytrap domain of the TAR2R1 subunit of the sweet receptor TAS1R2/TAS1R3 heterodimer and induces G protein-coupling [1]. This is the same binding site that is occupied by sucrose and other artificial sweetners such as sucralose.
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 COC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@H](CC(=O)O)N
Isomeric SMILES COC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@H](CC(=O)O)N
InChI InChI=1S/C14H18N2O5/c1-21-14(20)11(7-9-5-3-2-4-6-9)16-13(19)10(15)8-12(17)18/h2-6,10-11H,7-8,15H2,1H3,(H,16,19)(H,17,18)/t10-,11-/m0/s1
InChI Key IAOZJIPTCAWIRG-QWRGUYRKSA-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/)
Classification Click here for help
Compound class Peptide
IUPAC Name Click here for help
(3S)-3-amino-4-[[(2S)-1-methoxy-1-oxo-3-phenylpropan-2-yl]amino]-4-oxobutanoic acid
Synonyms Click here for help
Canderel® | NutraSweet® | SC18862
Database Links Click here for help
ChEBI CHEBI:2877
ChEMBL Ligand CHEMBL171679
DrugBank Ligand DB00168
GtoPdb PubChem SID 513757584
PubChem CID 134601
RCSB PDB Ligand PME
Search Google for chemical match using the InChIKey IAOZJIPTCAWIRG-QWRGUYRKSA-N
Search Google for chemicals with the same backbone IAOZJIPTCAWIRG
UniChem Compound Search for chemical match using the InChIKey IAOZJIPTCAWIRG-QWRGUYRKSA-N
UniChem Connectivity Search for chemical match using the InChIKey IAOZJIPTCAWIRG-QWRGUYRKSA-N