5-aminolevulinic acid   Click here for help

GtoPdb Ligand ID: 4784

Synonyms: 5-aminolevulinate | Ameluz® | D-aminolevulinic acid | Gliolan® | Levulan®
Approved drug PDB Ligand
5-aminolevulinic acid is an approved drug (FDA (1999)m EMA (2007))
Comment: Approved as aminolevulinic acid
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 2
Rotatable bonds 4
Topological polar surface area 80.39
Molecular weight 131.06
XLogP -1.55
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES NCC(=O)CCC(=O)O
Isomeric SMILES NCC(=O)CCC(=O)O
InChI InChI=1S/C5H9NO3/c6-3-4(7)1-2-5(8)9/h1-3,6H2,(H,8,9)
InChI Key ZGXJTSGNIOSYLO-UHFFFAOYSA-N
References
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. Bhardwaj RK, Herrera-Ruiz D, Sinko PJ, Gudmundsson OS, Knipp G. (2005)
Delineation of human peptide transporter 1 (hPepT1)-mediated uptake and transport of substrates with varying transporter affinities utilizing stably transfected hPepT1/Madin-Darby canine kidney clones and Caco-2 cells.
J Pharmacol Exp Ther, 314 (3): 1093-100. [PMID:15901802]
3. Döring F, Walter J, Will J, Föcking M, Boll M, Amasheh S, Clauss W, Daniel H. (1998)
Delta-aminolevulinic acid transport by intestinal and renal peptide transporters and its physiological and clinical implications.
J Clin Invest, 101 (12): 2761-7. [PMID:9637710]
4. 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]
5. Neumann J, Brandsch M. (2003)
Delta-aminolevulinic acid transport in cancer cells of the human extrahepatic biliary duct.
J Pharmacol Exp Ther, 305 (1): 219-24. [PMID:12649372]
6. 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]
7. Thwaites DT, Anderson CM. (2011)
The SLC36 family of proton-coupled amino acid transporters and their potential role in drug transport.
Br J Pharmacol, 164 (7): 1802-16. [PMID:21501141]
8. Xiang J, Hu Y, Smith DE, Keep RF. (2006)
PEPT2-mediated transport of 5-aminolevulinic acid and carnosine in astrocytes.
Brain Res, 1122 (1): 18-23. [PMID:17034769]