[3H]GlySar   Click here for help

GtoPdb Ligand ID: 4659

Synonyms: [3H]-GlySar | tritiated glycylsarcosine
 Ligand is labelled  Ligand is radioactive
Compound class: Synthetic organic

[3H]GlySar is commercially available from our sponsors

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 5
Hydrogen bond donors 2
Rotatable bonds 4
Topological polar surface area 83.63
Molecular weight 146.07
XLogP -4.04
No. Lipinski's rules broken 0

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 CN(C(=O)CN)CC(=O)O
Isomeric SMILES CN(C(=O)CN)CC(=O)O
InChI InChI=1S/C5H10N2O3/c1-7(3-5(9)10)4(8)2-6/h2-3,6H2,1H3,(H,9,10)
InChI Key VYAMLSCELQQRAE-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
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Interactions of the dipeptide ester prodrugs of acyclovir with the intestinal oligopeptide transporter: competitive inhibition of glycylsarcosine transport in human intestinal cell line-Caco-2.
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PepT1-mediated epithelial transport of dipeptides and cephalexin is enhanced by luminal leptin in the small intestine.
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3. Chu XY, Sánchez-Castaño GP, Higaki K, Oh DM, Hsu CP, Amidon GL. (2001)
Correlation between epithelial cell permeability of cephalexin and expression of intestinal oligopeptide transporter.
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Human dipeptide transporter, hPEPT1, stably transfected into Chinese hamster ovary cells.
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Significance and regional dependency of peptide transporter (PEPT) 1 in the intestinal permeability of glycylsarcosine: in situ single-pass perfusion studies in wild-type and Pept1 knockout mice.
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Human oligopeptide transporter 2 (PEPT2) mediates cellular uptake of polymyxins.
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Effects of frequently used pharmaceutical excipients on the organic cation transporters 1-3 and peptide transporters 1/2 stably expressed in MDCKII cells.
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10. Sala-Rabanal M, Loo DD, Hirayama BA, Turk E, Wright EM. (2006)
Molecular interactions between dipeptides, drugs and the human intestinal H+ -oligopeptide cotransporter hPEPT1.
J Physiol (Lond.), 574 (Pt 1): 149-66. [PMID:16627568]
11. Sala-Rabanal M, Loo DD, Hirayama BA, Wright EM. (2008)
Molecular mechanism of dipeptide and drug transport by the human renal H+/oligopeptide cotransporter hPEPT2.
Am J Physiol Renal Physiol, 294 (6): F1422-32. [PMID:18367661]
12. Song F, Hu Y, Jiang H, Smith DE. (2017)
Species Differences in Human and Rodent PEPT2-Mediated Transport of Glycylsarcosine and Cefadroxil in Pichia Pastoris Transformants.
Drug Metab Dispos, 45 (2): 130-136. [PMID:27836942]
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Expression profile and functional activity of peptide transporters in prostate cancer cells.
Mol Pharm, 10 (2): 477-87. [PMID:22950754]