Explore a selection of our essential drug information below, or:
Identification
- Generic Name
- Phloretin
- DrugBank Accession Number
- DB07810
- Background
Phloretin is a natural dihydrochalcone found in apples and many other fruits.
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for Phloretin (DB07810)
- Weight
- Average: 274.2687
Monoisotopic: 274.084123558 - Chemical Formula
- C15H14O5
- Synonyms
- 2',4,4',6'-Tetrahydroxy-Dihydrochalcone
- 2',4,4',6'-Tetrahydroxydihydrochalcone
- Dihydronaringenin
- Phloretol
- External IDs
- FEMA NO. 4390
Pharmacology
- Indication
Not Available
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Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism ASolute carrier family 23 member 1 inhibitorHumans UHTH-type transcriptional regulator TtgR Not Available Pseudomonas putida (strain DOT-T1E) - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as 2'-hydroxy-dihydrochalcones. These are organic compounds containing dihydrochalcone skeleton that carries a hydroxyl group at the 2'-position.
- Kingdom
- Organic compounds
- Super Class
- Phenylpropanoids and polyketides
- Class
- Linear 1,3-diarylpropanoids
- Sub Class
- Chalcones and dihydrochalcones
- Direct Parent
- 2'-Hydroxy-dihydrochalcones
- Alternative Parents
- Cinnamylphenols / Alkyl-phenylketones / Butyrophenones / Acylphloroglucinols and derivatives / Benzoyl derivatives / Aryl alkyl ketones / 1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / Vinylogous acids / Polyols show 2 more
- Substituents
- 1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / 2'-hydroxy-dihydrochalcone / Acylphloroglucinol derivative / Alkyl-phenylketone / Aromatic homomonocyclic compound / Aryl alkyl ketone / Aryl ketone / Benzenetriol / Benzenoid show 14 more
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- dihydrochalcones (CHEBI:17276) / dihydrochalcones, Chalcones and dihydrochalcones (C00774) / Chalcones and dihydrochalcones (LMPK12120525) / a small molecule (PHLORETIN)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- S5J5OE47MK
- CAS number
- 60-82-2
- InChI Key
- VGEREEWJJVICBM-UHFFFAOYSA-N
- 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
- IUPAC Name
- 3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)propan-1-one
- SMILES
- OC1=CC=C(CCC(=O)C2=C(O)C=C(O)C=C2O)C=C1
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0003306
- KEGG Compound
- C00774
- PubChem Compound
- 4788
- PubChem Substance
- 99444281
- ChemSpider
- 4624
- BindingDB
- 23446
- 1368167
- ChEBI
- 17276
- ChEMBL
- CHEMBL45068
- ZINC
- ZINC000000047553
- Guide to Pharmacology
- GtP Drug Page
- PDBe Ligand
- G50
- Wikipedia
- Phloretin
- PDB Entries
- 2uxi / 6l5r / 6l5s
Clinical Trials
- Clinical Trials
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Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.132 mg/mL ALOGPS logP 2.23 ALOGPS logP 3.9 Chemaxon logS -3.3 ALOGPS pKa (Strongest Acidic) 7.96 Chemaxon pKa (Strongest Basic) -4.6 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 4 Chemaxon Polar Surface Area 97.99 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 73.71 m3·mol-1 Chemaxon Polarizability 27.75 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.8742 Blood Brain Barrier + 0.699 Caco-2 permeable + 0.8866 P-glycoprotein substrate Non-substrate 0.5748 P-glycoprotein inhibitor I Non-inhibitor 0.9427 P-glycoprotein inhibitor II Non-inhibitor 0.8578 Renal organic cation transporter Non-inhibitor 0.8001 CYP450 2C9 substrate Non-substrate 0.7142 CYP450 2D6 substrate Non-substrate 0.8806 CYP450 3A4 substrate Non-substrate 0.5785 CYP450 1A2 substrate Inhibitor 0.9108 CYP450 2C9 inhibitor Inhibitor 0.8948 CYP450 2D6 inhibitor Non-inhibitor 0.7867 CYP450 2C19 inhibitor Inhibitor 0.8993 CYP450 3A4 inhibitor Inhibitor 0.7961 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.7172 Ames test Non AMES toxic 0.9132 Carcinogenicity Non-carcinogens 0.9099 Biodegradation Not ready biodegradable 0.6501 Rat acute toxicity 2.0976 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8407 hERG inhibition (predictor II) Non-inhibitor 0.8737
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 175.5077611 predictedDarkChem Lite v0.1.0 [M-H]- 175.6950611 predictedDarkChem Lite v0.1.0 [M-H]- 175.4200611 predictedDarkChem Lite v0.1.0 [M-H]- 164.93633 predictedDeepCCS 1.0 (2019) [M+H]+ 176.9809611 predictedDarkChem Lite v0.1.0 [M+H]+ 177.8200611 predictedDarkChem Lite v0.1.0 [M+H]+ 177.6072611 predictedDarkChem Lite v0.1.0 [M+H]+ 167.29433 predictedDeepCCS 1.0 (2019) [M+Na]+ 177.3145611 predictedDarkChem Lite v0.1.0 [M+Na]+ 177.2860611 predictedDarkChem Lite v0.1.0 [M+Na]+ 177.6440611 predictedDarkChem Lite v0.1.0 [M+Na]+ 173.38748 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Sodium:ascorbate cotransporter. Mediates electrogenic uptake of vitamin C, with a stoichiometry of 2 Na(+) for each ascorbate (PubMed:10556483, PubMed:10556521, PubMed:10631088, PubMed:36749388). Has retained some ancestral activity toward nucleobases such as urate, an oxidized purine. Low-affinity high-capacity sodium:urate cotransporter, may regulate serum urate levels by serving as a renal urate re-absorber (PubMed:36749388)
- Specific Function
- Dehydroascorbic acid transmembrane transporter activity
- Gene Name
- SLC23A1
- Uniprot ID
- Q9UHI7
- Uniprot Name
- Solute carrier family 23 member 1
- Molecular Weight
- 64814.445 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Pseudomonas putida (strain DOT-T1E)
- Pharmacological action
- Unknown
- General Function
- Dna binding
- Specific Function
- Represses expression from the ttgABC operon promoter and its own expression. Binds to a promoter region between the divergently transcribed ttgR and ttgABC genes/operons; in the presence of chloram...
- Gene Name
- ttgR
- Uniprot ID
- Q9AIU0
- Uniprot Name
- HTH-type transcriptional regulator TtgR
- Molecular Weight
- 23854.075 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Drug created at September 15, 2010 21:26 / Updated at August 26, 2024 19:21