L-phenylalanine   Click here for help

GtoPdb Ligand ID: 3313

Abbreviated name: L-Phe
PDB Ligand
Compound class: Metabolite or derivative
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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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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
Natural/Endogenous Targets
Target
GPR139
Enzymes Catalysing Reactions with this Compound as a Substrate or Product
Enzyme EC number Reaction Reference
L-Phenylalanine hydroxylase 1.14.16.1 L-phenylalanine + O2 -> L-tyrosine
Transporters Moving this Compound Across a Lipid Membrane
Transporter EC number Reaction Reference
Monocarboxylate transporter 10
L-type amino acid transporter 3 1
L-type amino acid transporter 4
ATB0,+ 8
B0AT1 2
B0AT2 2
B0AT3 9
sodium-coupled neutral amino acid transporter 2 5
sodium-coupled neutral amino acid transporter 4 4
Selectivity at GPCRs
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
GPR139 Primary target of this compound Ligand is endogenous in the given species Hs Agonist Agonist 3.1 pKi - 7
⤷ pKi 3.1 (Ki 8.72x10-4 M) [7]
Description: Inhibition equilibrium constant from a radioligand membrane binding assay.
GPR139 Primary target of this compound Ligand is endogenous in the given species Hs Agonist Agonist 3.5 pEC50 - 6
⤷ pEC50 3.5 (EC50 3.2x10-4 M) [6]
GPR139 Primary target of this compound Ligand is endogenous in the given species Hs Agonist Agonist 4.5 pIC50 - 7
⤷ pIC50 4.5 (IC50 3.1x10-5 M) [7]
Description: Measured using a GTPγS assay in transfected COS7 cells.
Additional information and targets (data relate to human unless otherwise stated)
Description Data Reference
Endogenous substrates at ATB0,+ L-isoleucine > L-leucine, L-methionine > L-phenylalanine > L-tryptophan > L-valine > L-serine 8
Endogenous substrates at B0AT1 L-leucine, L-methionine, L-isoleucine, L-valine > L-asparagine, L-phenylalanine, L-alanine, L-serine > L-threonine, glycine, L-proline 2
Endogenous substrates at B0AT2 L-proline > L-alanine, L-valine, L-methionine, L-leucine > L-isoleucine, L-threonine, L-asparagine, L-serine, L-phenylalanine > glycine 2
Endogenous substrates at B0AT3 L-alanine, glycine > L-methionine, L-phenylalanine, L-leucine, L-histidine, L-glutamine 9
Substrates at sodium-coupled neutral amino acid transporter 2 L-alanine, L-methionine > L-asparagine, L-glutamine, L-serine, L-proline, glycine > L-threonine, L-leucine, L-phenylalanine 5
Substrates at sodium-coupled neutral amino acid transporter 4 L-histidine > L-arginine, L-alanine, L-asparagine, L-lysine > glycine, L-glutamine, L-serine, L-proline, L-leucine, L-phenylalanine 4
Amino-acid rank order of potency at CaS receptor L-phenylalanine, L-tryptophan, L-histidine > L-alanine > L-serine, L-proline, L-glutamic acid > L-aspartic acid (not L-lysine, L-arginine, L-leucine and L-isoleucine) 3
Ligand mentioned in the following text fields
Catecholamine turnover overview