4-AMBA   Click here for help

GtoPdb Ligand ID: 4702

PDB Ligand
Compound class: Synthetic organic
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 2
Rotatable bonds 2
Topological polar surface area 63.32
Molecular weight 151.06
XLogP 0.76
No. Lipinski's rules broken 0
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Canonical SMILES NCc1ccc(cc1)C(=O)O
Isomeric SMILES NCc1ccc(cc1)C(=O)O
InChI InChI=1S/C8H9NO2/c9-5-6-1-3-7(4-2-6)8(10)11/h1-4H,5,9H2,(H,10,11)
1. Anderson CM, Jevons M, Thangaraju M, Edwards N, Conlon NJ, Woods S, Ganapathy V, Thwaites DT. (2010)
Transport of the photodynamic therapy agent 5-aminolevulinic acid by distinct H+-coupled nutrient carriers coexpressed in the small intestine.
J Pharmacol Exp Ther, 332 (1): 220-8. [PMID:19789362]
2. Biegel A, Knütter I, Hartrodt B, Gebauer S, Theis S, Luckner P, Kottra G, Rastetter M, Zebisch K, Thondorf I et al.. (2006)
The renal type H+/peptide symporter PEPT2: structure-affinity relationships.
Amino Acids, 31 (2): 137-56. [PMID:16868651]
3. Darcel NP, Liou AP, Tomé D, Raybould HE. (2005)
Activation of vagal afferents in the rat duodenum by protein digests requires PepT1.
J Nutr, 135 (6): 1491-5. [PMID:15930458]
4. Meredith D, Boyd CA, Bronk JR, Bailey PD, Morgan KM, Collier ID, Temple CS. (1998)
4-aminomethylbenzoic acid is a non-translocated competitive inhibitor of the epithelial peptide transporter PepT1.
J Physiol (Lond.), 512 ( Pt 3): 629-34. [PMID:9882198]
5. Theis S, Knutter I, Hartrodt B, Brandsch M, Kottra G, Neubert K, Daniel H. (2002)
Synthesis and characterization of high affinity inhibitors of the H+/peptide transporter PEPT2.
J Biol Chem, 277 (9): 7287-92. [PMID:11751927]