phloretin   Click here for help

GtoPdb Ligand ID: 4285

PDB Ligand
Compound class: Natural product
Comment: Found in apple tree leaves and in the Manchurian apricot. Another naturally occuring organic molecule, phlorizin, which is found in the bark of several types of fruit tree, is converted into phloretin in the body by hydrolytic enzymes.
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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

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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 Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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 1
Hydrogen bond donors 4
Rotatable bonds 4
Topological polar surface area 97.99
Molecular weight 274.08
XLogP 2.83
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES Oc1ccc(cc1)CCC(=O)c1c(O)cc(cc1O)O
Isomeric SMILES Oc1ccc(cc1)CCC(=O)c1c(O)cc(cc1O)O
InChI InChI=1S/C15H14O5/c16-10-4-1-9(2-5-10)3-6-12(18)15-13(19)7-11(17)8-14(15)20/h1-2,4-5,7-8,16-17,19-20H,3,6H2
InChI Key VGEREEWJJVICBM-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Selectivity at GPCRs
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
TAS2R14 Hs Agonist Agonist 4.5 pEC50 - 2
⤷ pEC50 4.5 (EC50 3.02x10-5 M) [2]
TAS2R39 Hs Agonist Agonist 4.4 pEC50 - 2
⤷ pEC50 4.4 (EC50 4.13x10-5 M) [2]
Selectivity at ion channels
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
ClC-3 Hs Channel blocker - 4.5 pIC50 -
⤷ pIC50 4.5 (IC50 3x10-5 M)
AQP9 Hs Inhibitor - - - -
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Selectivity at transporters
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
Sodium-dependent vitamin C transporter 1 Hs Inhibitor Inhibition 4.2 pKi - 3
⤷ pKi 4.2 (Ki 6.5x10-5 M) [3]
major facilitator superfamily domain containing 4B Rn Inhibitor Inhibition - - - 1
⤷ [1]
Ligand mentioned in the following text fields
Class I transporters overview
Proton-coupled inositol transporter overview
SLC23 family of ascorbic acid transporters overview