[14C]GlySar   Click here for help

GtoPdb Ligand ID: 4599

Synonyms: [14C]-GlySar | glycylsarcosine
 Ligand is labelled  Ligand is radioactive
Compound class: Synthetic organic
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 CDK toolkit. 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
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.

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Canonical SMILES CN(C(=O)CN)CC(=O)O
Isomeric SMILES CN([14C](=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)/i4+2
InChI Key VYAMLSCELQQRAE-DOMIDYPGSA-N
References
1. Akazawa T, Yoshida S, Ohnishi S, Kanazu T, Kawai M, Takahashi K. (2018)
Application of Intestinal Epithelial Cells Differentiated from Human Induced Pluripotent Stem Cells for Studies of Prodrug Hydrolysis and Drug Absorption in the Small Intestine.
Drug Metab Dispos, 46 (11): 1497-1506. [PMID:30135242]
2. Balimane PV, Tamai I, Guo A, Nakanishi T, Kitada H, Leibach FH, Tsuji A, Sinko PJ. (1998)
Direct evidence for peptide transporter (PepT1)-mediated uptake of a nonpeptide prodrug, valacyclovir.
Biochem Biophys Res Commun, 250 (2): 246-51. [PMID:9753615]
3. Biegel A, Gebauer S, Hartrodt B, Brandsch M, Neubert K, Thondorf I. (2005)
Three-dimensional quantitative structure-activity relationship analyses of beta-lactam antibiotics and tripeptides as substrates of the mammalian H+/peptide cotransporter PEPT1.
J Med Chem, 48 (13): 4410-9. [PMID:15974593]
4. Fujita T, Kishida T, Wada M, Okada N, Yamamoto A, Leibach FH, Ganapathy V. (2004)
Functional characterization of brain peptide transporter in rat cerebral cortex: identification of the high-affinity type H+/peptide transporter PEPT2.
Brain Res, 997 (1): 52-61. [PMID:14715149]
5. Ganapathy ME, Brandsch M, Prasad PD, Ganapathy V, Leibach FH. (1995)
Differential recognition of beta -lactam antibiotics by intestinal and renal peptide transporters, PEPT 1 and PEPT 2.
J Biol Chem, 270 (43): 25672-7. [PMID:7592745]
6. Ganapathy ME, Huang W, Wang H, Ganapathy V, Leibach FH. (1998)
Valacyclovir: a substrate for the intestinal and renal peptide transporters PEPT1 and PEPT2.
Biochem Biophys Res Commun, 246 (2): 470-5. [PMID:9610386]
7. Ganapathy ME, Prasad PD, Mackenzie B, Ganapathy V, Leibach FH. (1997)
Interaction of anionic cephalosporins with the intestinal and renal peptide transporters PEPT 1 and PEPT 2.
Biochim Biophys Acta, 1324 (2): 296-308. [PMID:9092716]
8. Hu Y, Xie Y, Keep RF, Smith DE. (2014)
Divergent developmental expression and function of the proton-coupled oligopeptide transporters PepT2 and PhT1 in regional brain slices of mouse and rat.
J Neurochem, 129 (6): 955-65. [PMID:24548120]
9. Irie M, Terada T, Sawada K, Saito H, Inui K. (2001)
Recognition and transport characteristics of nonpeptidic compounds by basolateral peptide transporter in Caco-2 cells.
J Pharmacol Exp Ther, 298 (2): 711-7. [PMID:11454935]
10. Knütter I, Kottra G, Fischer W, Daniel H, Brandsch M. (2009)
High-affinity interaction of sartans with H+/peptide transporters.
Drug Metab Dispos, 37 (1): 143-9. [PMID:18824524]
11. Knütter I, Theis S, Hartrodt B, Born I, Brandsch M, Daniel H, Neubert K. (2001)
A novel inhibitor of the mammalian peptide transporter PEPT1.
Biochemistry, 40 (14): 4454-8. [PMID:11284702]
12. Knütter I, Wollesky C, Kottra G, Hahn MG, Fischer W, Zebisch K, Neubert RH, Daniel H, Brandsch M. (2008)
Transport of angiotensin-converting enzyme inhibitors by H+/peptide transporters revisited.
J Pharmacol Exp Ther, 327 (2): 432-41. [PMID:18713951]
13. Liu W, Liang R, Ramamoorthy S, Fei YJ, Ganapathy ME, Hediger MA, Ganapathy V, Leibach FH. (1995)
Molecular cloning of PEPT 2, a new member of the H+/peptide cotransporter family, from human kidney.
Biochim Biophys Acta, 1235 (2): 461-6. [PMID:7756356]
14. Luckner P, Brandsch M. (2005)
Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1.
Eur J Pharm Biopharm, 59 (1): 17-24. [PMID:15567297]
15. Mandal A, Pal D, Mitra AK. (2016)
Circumvention of P-gp and MRP2 mediated efflux of lopinavir by a histidine based dipeptide prodrug.
Int J Pharm, 512 (1): 49-60. [PMID:27543355]
16. Sawada K, Terada T, Saito H, Hashimoto Y, Inui K. (1999)
Effects of glibenclamide on glycylsarcosine transport by the rat peptide transporters PEPT1 and PEPT2.
Br J Pharmacol, 128 (6): 1159-64. [PMID:10578127]
17. Tamai I, Nakanishi T, Hayashi K, Terao T, Sai Y, Shiraga T, Miyamoto K, Takeda E, Higashida H, Tsuji A. (1997)
The predominant contribution of oligopeptide transporter PepT1 to intestinal absorption of beta-lactam antibiotics in the rat small intestine.
J Pharm Pharmacol, 49 (8): 796-801. [PMID:9379359]
18. Terada T, Saito H, Mukai M, Inui K. (1997)
Recognition of beta-lactam antibiotics by rat peptide transporters, PEPT1 and PEPT2, in LLC-PK1 cells.
Am J Physiol, 273 (5 Pt 2): F706-11. [PMID:9374833]
19. Terada T, Saito H, Mukai M, Inui KI. (1996)
Identification of the histidine residues involved in substrate recognition by a rat H+/peptide cotransporter, PEPT1.
FEBS Lett, 394 (2): 196-200. [PMID:8843163]
20. Terada T, Sawada K, Saito H, Hashimoto Y, Inui K. (2000)
Inhibitory effect of novel oral hypoglycemic agent nateglinide (AY4166) on peptide transporters PEPT1 and PEPT2.
Eur J Pharmacol, 392 (1-2): 11-7. [PMID:10748266]