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))
Compound class: Metabolite or derivative
Comment: Approved as aminolevulinic acid
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species
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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Click here for structure editor
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 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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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 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. Kinoshita H, Kanda T, Takata T, Sugihara T, Mae Y, Yamashita T, Onoyama T, Takeda Y, Isomoto H. (2020)
Oligopeptide Transporter-1 is Associated with Fluorescence Intensity of 5-Aminolevulinic Acid-Based Photodynamic Diagnosis in Pancreatic Cancer Cells.
Yonago Acta Med, 63 (3): 154-162. [PMID:32884434]
6. Labib PL, Yaghini E, Davidson BR, MacRobert AJ, Pereira SP. (2021)
5-Aminolevulinic acid for fluorescence-guided surgery in pancreatic cancer: Cellular transport and fluorescence quantification studies.
Transl Oncol, 14 (1): 100886. [PMID:33059124]
7. 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]
8. 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]
9. 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]
10. 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]