[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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Physico-chemical Properties
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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
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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
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]