LIPID MAPS

Structure Database (LMSD)

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Common Name

Phloretin

Systematic Name

Synonyms

LM ID

LMPK12120525

Formula

C₁₅H₁₄O₅

Exact Mass

Calculate m/z

274.084125

Status

Curated

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Classification

Category

Main Class

Sub Class

Polyketides [PK]

Flavonoids [PK12]

Chalcones and dihydrochalcones [PK1212]

Biological Context

Phloretin is a natural phenol which inhibits a variety of transporters. It inhibits the monocarboxylate transporters MCT1 and MCT2 (IC50 = 28 and 14 µM, respectively), restricting the rapid transport of monocarboxylates like lactate and pyruvate across the plasma membrane.¹ Phloretin also blocks the sodium/D-glucose cotransporter (Ki = 86 µM) and the human concentrative nucleoside transporter 3 (Ki = 32 µM).^2,3

This information has been provided by Cayman Chemical

References

1. Bröer, S., Bröer, A., Schneider, H.P., et al. Characterization of the high-affinity monocarboxylate transporter MCT2 in Xenopus laevis oocytes. Biochem. J. 341(Pt 3), 529-535 (1999).

2. Gupte, A., and Buolamwini, J.K. Synthesis and biological evaluation of phloridzin analogs as human concentrative nucleoside transporter 3 (hCNT3) inhibitors. Bioorg. Med. Chem. Lett. 19(3), 917-921 (2009).

3. Wielert-Badt, S., Lin, J.T., Lorenz, M., et al. Probing the conformation of the sugar transport inhibitor phlorizin by 2D-NMR, molecular dynamics studies, and pharmacophore analysis. J. Med. Chem. 43(9), 1692-1698 (2000).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Viridiplantae (#33090)

Flavonoid imported from http://metabolomics.jp/

String Representations

InChiKey (Click to copy)

VGEREEWJJVICBM-UHFFFAOYSA-N

InChi (Click to copy)

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

SMILES (Click to copy)

C1(O)C=C(O)C(C(=O)CCC2C=CC(O)=CC=2)=C(O)C=1

Other Databases

Wikipedia

KEGG ID

HMDB ID

CHEBI ID

METABOLOMICS ID

PubChem CID

Cayman ID

PDB ID

GuidePharm ID

Calculated Physicochemical Properties

Heavy Atoms 20

Rings 2

Aromatic Rings 2

Rotatable Bonds 4

Van der Waals Molecular Volume 247.01

Topological Polar Surface Area 97.99

Hydrogen Bond Donors 4

Hydrogen Bond Acceptors 5

logP 2.32

Molar Refractivity 72.19

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