L-phenylalanine   Click here for help

GtoPdb Ligand ID: 3313

Abbreviated name: L-Phe
PDB Ligand
Compound class: Metabolite
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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 3
Hydrogen bond donors 2
Rotatable bonds 3
Topological polar surface area 63.32
Molecular weight 165.08
XLogP -1.38
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 NC(C(=O)O)Cc1ccccc1
Isomeric SMILES N[C@H](C(=O)O)Cc1ccccc1
InChI InChI=1S/C9H11NO2/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5,8H,6,10H2,(H,11,12)/t8-/m0/s1
InChI Key COLNVLDHVKWLRT-QMMMGPOBSA-N
References
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Identification of a novel system L amino acid transporter structurally distinct from heterodimeric amino acid transporters.
J Biol Chem, 278 (44): 43838-45. [PMID:12930836]
2. Bröer S. (2006)
The SLC6 orphans are forming a family of amino acid transporters.
Neurochem Int, 48 (6-7): 559-67. [PMID:16540203]
3. Conigrave AD, Quinn SJ, Brown EM. (2000)
L-amino acid sensing by the extracellular Ca2+-sensing receptor.
Proc Natl Acad Sci USA, 97 (9): 4814-9. [PMID:10781086]
4. Hatanaka T, Huang W, Ling R, Prasad PD, Sugawara M, Leibach FH, Ganapathy V. (2001)
Evidence for the transport of neutral as well as cationic amino acids by ATA3, a novel and liver-specific subtype of amino acid transport system A.
Biochim Biophys Acta, 1510 (1-2): 10-7. [PMID:11342143]
5. Hatanaka T, Huang W, Wang H, Sugawara M, Prasad PD, Leibach FH, Ganapathy V. (2000)
Primary structure, functional characteristics and tissue expression pattern of human ATA2, a subtype of amino acid transport system A.
Biochim Biophys Acta, 1467 (1): 1-6. [PMID:10930503]
6. Isberg V, Andersen KB, Bisig C, Dietz GP, Bräuner-Osborne H, Gloriam DE. (2014)
Computer-aided discovery of aromatic l-α-amino acids as agonists of the orphan G protein-coupled receptor GPR139.
J Chem Inf Model, 54 (6): 1553-7. [PMID:24826842]
7. Liu C, Bonaventure P, Lee G, Nepomuceno D, Kuei C, Wu J, Li Q, Joseph V, Sutton SW, Eckert W et al.. (2015)
GPR139, an Orphan Receptor Highly Enriched in the Habenula and Septum, Is Activated by the Essential Amino Acids L-Tryptophan and L-Phenylalanine.
Mol Pharmacol, 88 (5): 911-25. [PMID:26349500]
8. Sloan JL, Mager S. (1999)
Cloning and functional expression of a human Na(+) and Cl(-)-dependent neutral and cationic amino acid transporter B(0+).
J Biol Chem, 274 (34): 23740-5. [PMID:10446133]
9. Vanslambrouck JM, Bröer A, Thavyogarajah T, Holst J, Bailey CG, Bröer S, Rasko JE. (2010)
Renal imino acid and glycine transport system ontogeny and involvement in developmental iminoglycinuria.
Biochem J, 428 (3): 397-407. [PMID:20377526]