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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 15:12:49 UTC
Update Date2022-03-07 02:49:18 UTC
HMDB IDHMDB0003306
Secondary Accession Numbers
  • HMDB03306
Metabolite Identification
Common NamePhloretin
DescriptionPhloretin is the aglucone of phlorizin, a plant-derived dihydrochalcone phytochemical reported to promote potent antioxidative activities in peroxynitrite scavenging and the inhibition of lipid peroxidation. Phloretin, which is present in apples, pears and tomatoes, has been found to inhibit the growth of several cancer cells and induce apoptosis of B16 melanoma and HL60 human leukemia cells. Phloretin also inhibits HT-29 cell growth by inducing apoptosis, which may be mediated through changes in mitochondrial membrane permeability and activation of the caspase pathways. Phloretin is a well-known inhibitor of eukaryotic urea transporters, blocks VacA-mediated urea and ion transport (PMID:18158826 , 11560962 , 18063724 , 15671209 , 12083758 ). Phloretin is a biomarker for the consumption of apples. Phloretin has been found to be a metabolite of Escherichia (PMID:23542617 ).
Structure
Data?1582752269
Synonyms
ValueSource
3-(4-Hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)-1-propanoneChEBI
2,6-Dihydroxy-4-methoxyacetophenoneHMDB
4-O-MethylphloracetophenoneHMDB
DihydronaringeninHMDB
PhloretolHMDB
Chemical FormulaC15H14O5
Average Molecular Weight274.2687
Monoisotopic Molecular Weight274.084123558
IUPAC Name3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)propan-1-one
Traditional Namephloretin
CAS Registry Number60-82-2
SMILES
OC1=CC=C(CCC(=O)C2=C(O)C=C(O)C=C2O)C=C1
InChI Identifier
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 KeyVGEREEWJJVICBM-UHFFFAOYSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassLinear 1,3-diarylpropanoids
Sub ClassChalcones and dihydrochalcones
Direct Parent2'-Hydroxy-dihydrochalcones
Alternative Parents
Substituents
  • 2'-hydroxy-dihydrochalcone
  • Cinnamylphenol
  • Alkyl-phenylketone
  • Acylphloroglucinol derivative
  • Butyrophenone
  • Benzenetriol
  • Phloroglucinol derivative
  • Phenylketone
  • Aryl alkyl ketone
  • Aryl ketone
  • Benzoyl
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Benzenoid
  • Monocyclic benzene moiety
  • Vinylogous acid
  • Ketone
  • Polyol
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point263.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.12 mg/mL at 16 °CNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available160.699http://allccs.zhulab.cn/database/detail?ID=AllCCS00001447
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.13 g/LALOGPS
logP2.23ALOGPS
logP3.9ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)7.96ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity73.71 m³·mol⁻¹ChemAxon
Polarizability27.75 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+164.8531661259
DarkChem[M-H]-165.1831661259
DeepCCS[M+H]+167.29430932474
DeepCCS[M-H]-164.93630932474
DeepCCS[M-2H]-197.82230932474
DeepCCS[M+Na]+173.38730932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
PhloretinOC1=CC=C(CCC(=O)C2=C(O)C=C(O)C=C2O)C=C14116.8Standard polar33892256
PhloretinOC1=CC=C(CCC(=O)C2=C(O)C=C(O)C=C2O)C=C12681.0Standard non polar33892256
PhloretinOC1=CC=C(CCC(=O)C2=C(O)C=C(O)C=C2O)C=C12884.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Phloretin,1TMS,isomer #1C[Si](C)(C)OC1=CC=C(CCC(=O)C2=C(O)C=C(O)C=C2O)C=C12703.2Semi standard non polar33892256
Phloretin,1TMS,isomer #2C[Si](C)(C)OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C12768.5Semi standard non polar33892256
Phloretin,1TMS,isomer #3C[Si](C)(C)OC1=CC(O)=C(C(=O)CCC2=CC=C(O)C=C2)C(O)=C12769.1Semi standard non polar33892256
Phloretin,2TMS,isomer #1C[Si](C)(C)OC1=CC=C(CCC(=O)C2=C(O)C=C(O)C=C2O[Si](C)(C)C)C=C12662.5Semi standard non polar33892256
Phloretin,2TMS,isomer #2C[Si](C)(C)OC1=CC=C(CCC(=O)C2=C(O)C=C(O[Si](C)(C)C)C=C2O)C=C12638.2Semi standard non polar33892256
Phloretin,2TMS,isomer #3C[Si](C)(C)OC1=CC(O)=C(C(=O)CCC2=CC=C(O)C=C2)C(O[Si](C)(C)C)=C12704.9Semi standard non polar33892256
Phloretin,2TMS,isomer #4C[Si](C)(C)OC1=CC(O)=CC(O[Si](C)(C)C)=C1C(=O)CCC1=CC=C(O)C=C12742.2Semi standard non polar33892256
Phloretin,3TMS,isomer #1C[Si](C)(C)OC1=CC=C(CCC(=O)C2=C(O[Si](C)(C)C)C=C(O)C=C2O[Si](C)(C)C)C=C12699.4Semi standard non polar33892256
Phloretin,3TMS,isomer #2C[Si](C)(C)OC1=CC=C(CCC(=O)C2=C(O)C=C(O[Si](C)(C)C)C=C2O[Si](C)(C)C)C=C12653.9Semi standard non polar33892256
Phloretin,3TMS,isomer #3C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=C(C(=O)CCC2=CC=C(O)C=C2)C(O[Si](C)(C)C)=C12672.1Semi standard non polar33892256
Phloretin,4TMS,isomer #1C[Si](C)(C)OC1=CC=C(CCC(=O)C2=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C2O[Si](C)(C)C)C=C12742.9Semi standard non polar33892256
Phloretin,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(CCC(=O)C2=C(O)C=C(O)C=C2O)C=C12987.5Semi standard non polar33892256
Phloretin,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C13050.3Semi standard non polar33892256
Phloretin,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC(O)=C(C(=O)CCC2=CC=C(O)C=C2)C(O)=C13043.3Semi standard non polar33892256
Phloretin,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(CCC(=O)C2=C(O)C=C(O)C=C2O[Si](C)(C)C(C)(C)C)C=C13194.3Semi standard non polar33892256
Phloretin,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C(CCC(=O)C2=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C2O)C=C13179.8Semi standard non polar33892256
Phloretin,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC(O)=C(C(=O)CCC2=CC=C(O)C=C2)C(O[Si](C)(C)C(C)(C)C)=C13222.0Semi standard non polar33892256
Phloretin,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC1=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C1C(=O)CCC1=CC=C(O)C=C13282.2Semi standard non polar33892256
Phloretin,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(CCC(=O)C2=C(O[Si](C)(C)C(C)(C)C)C=C(O)C=C2O[Si](C)(C)C(C)(C)C)C=C13460.0Semi standard non polar33892256
Phloretin,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C(CCC(=O)C2=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C2O[Si](C)(C)C(C)(C)C)C=C13412.1Semi standard non polar33892256
Phloretin,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC(O[Si](C)(C)C(C)(C)C)=C(C(=O)CCC2=CC=C(O)C=C2)C(O[Si](C)(C)C(C)(C)C)=C13411.3Semi standard non polar33892256
Phloretin,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(CCC(=O)C2=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C=C2O[Si](C)(C)C(C)(C)C)C=C13679.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Phloretin GC-EI-TOF (Non-derivatized)splash10-002f-0915000000-2cd118505cf4ff16b6642017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Phloretin GC-EI-TOF (Non-derivatized)splash10-002f-0915000000-2cd118505cf4ff16b6642018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Phloretin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-2920000000-ce9a5fce0e77c981b6d32017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Phloretin GC-MS (4 TMS) - 70eV, Positivesplash10-00r2-2207490000-670b5b16c28fb6b692e32017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Phloretin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Phloretin Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-0006-1900000000-b990d3eca878be81222b2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phloretin Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-014i-2900000000-4eb9bf83b7d70a97bd0b2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phloretin Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-0w2c-4900000000-77d3779ddd5455f0b9a32012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phloretin LC-ESI-ITTOF (LCMS-IT-TOF) , Positive-QTOFsplash10-004i-0090000000-a2a168a2f04c479df8ed2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phloretin LC-ESI-ITTOF (LCMS-IT-TOF) , Negative-QTOFsplash10-00dj-0090050000-15d417468db5c396463e2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phloretin LC-ESI-ITTOF (LCMS-IT-TOF) , Positive-QTOFsplash10-0a4i-0900000000-bc6e2e1009d1b50ad9f72012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phloretin LC-ESI-QTOF , negative-QTOFsplash10-00xr-0690000000-e5774d71d08a1df833362017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phloretin LC-ESI-QTOF , negative-QTOFsplash10-014i-0900000000-d051b74295a78047c5f02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phloretin LC-ESI-QTOF , negative-QTOFsplash10-01b9-0900000000-6e6539df4cbbef8d26b32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phloretin Linear Ion Trap , negative-QTOFsplash10-01b9-0940000000-e06c676ae64bfbb5107b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phloretin Linear Ion Trap , negative-QTOFsplash10-014i-0900000000-949e95a0767d512e3d042017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phloretin Linear Ion Trap , negative-QTOFsplash10-014i-0910000000-bb2134d05e29fff0bc782017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phloretin Linear Ion Trap , negative-QTOFsplash10-014i-0910000000-eb3ed13a8222a6f196222017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phloretin 10V, Positive-QTOFsplash10-004i-0290000000-826fa92be2be280f2e5e2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phloretin 20V, Positive-QTOFsplash10-0zfr-0930000000-6abeede53ef1753e26132015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phloretin 40V, Positive-QTOFsplash10-0udi-2900000000-a2ba5d714e72373837bb2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phloretin 10V, Negative-QTOFsplash10-00di-0290000000-8a18e7ae5b70f7a0683f2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phloretin 20V, Negative-QTOFsplash10-00b9-0930000000-66ecbda03ca96ea053b32015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phloretin 40V, Negative-QTOFsplash10-004i-3910000000-831048d96d049d47cd922015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phloretin 10V, Positive-QTOFsplash10-004i-0290000000-826fa92be2be280f2e5e2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phloretin 20V, Positive-QTOFsplash10-0zfr-0930000000-6abeede53ef1753e26132015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phloretin 40V, Positive-QTOFsplash10-0udi-2900000000-a2ba5d714e72373837bb2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phloretin 10V, Negative-QTOFsplash10-00di-0290000000-8a18e7ae5b70f7a0683f2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phloretin 20V, Negative-QTOFsplash10-00b9-0930000000-66ecbda03ca96ea053b32015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phloretin 40V, Negative-QTOFsplash10-004i-3910000000-831048d96d049d47cd922015-05-27Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)2012-12-05Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Fibroblasts
  • Intestine
  • Platelet
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.0152 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.0420 +/- 0.0500 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.0487 +/- 0.127 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 108 details
UrineDetected and Quantified50 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified40 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.098 +/- 0.10 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.046 +/- 0.026 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.0247 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.0525 +/- 0.0510 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB07810
Phenol Explorer Compound ID108
FooDB IDFDB015553
KNApSAcK IDC00007936
Chemspider ID4624
KEGG Compound IDC00774
BioCyc IDPHLORETIN
BiGG IDNot Available
Wikipedia LinkPhloretin
METLIN ID3405
PubChem Compound4788
PDB IDNot Available
ChEBI ID17276
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00000417
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Sharif NA, Crider JY, Davis TL: AL-3138 antagonizes FP prostanoid receptor-mediated inositol phosphates generation: comparison with some purported FP antagonists. J Pharm Pharmacol. 2000 Dec;52(12):1529-39. [PubMed:11197083 ]
  2. DuPont MS, Bennett RN, Mellon FA, Williamson G: Polyphenols from alcoholic apple cider are absorbed, metabolized and excreted by humans. J Nutr. 2002 Feb;132(2):172-5. [PubMed:11823574 ]
  3. Ito H, Gonthier MP, Manach C, Morand C, Mennen L, Remesy C, Scalbert A: Polyphenol levels in human urine after intake of six different polyphenol-rich beverages. Br J Nutr. 2005 Oct;94(4):500-9. [PubMed:16197573 ]
  4. Nielsen SE, Freese R, Kleemola P, Mutanen M: Flavonoids in human urine as biomarkers for intake of fruits and vegetables. Cancer Epidemiol Biomarkers Prev. 2002 May;11(5):459-66. [PubMed:12010860 ]
  5. Fan HT, Morishima S, Kida H, Okada Y: Phloretin differentially inhibits volume-sensitive and cyclic AMP-activated, but not Ca-activated, Cl(-) channels. Br J Pharmacol. 2001 Aug;133(7):1096-106. [PubMed:11487521 ]
  6. Stangl V, Lorenz M, Ludwig A, Grimbo N, Guether C, Sanad W, Ziemer S, Martus P, Baumann G, Stangl K: The flavonoid phloretin suppresses stimulated expression of endothelial adhesion molecules and reduces activation of human platelets. J Nutr. 2005 Feb;135(2):172-8. [PubMed:15671209 ]
  7. Rasmussen SE, Breinholt VM: Non-nutritive bioactive food constituents of plants: bioavailability of flavonoids. Int J Vitam Nutr Res. 2003 Mar;73(2):101-11. [PubMed:12747217 ]
  8. Zerbini G, Podesta F, Meregalli G, Deferrari G, Pontremoli R: Fibroblast Na+-Li+ countertransport rate is elevated in essential hypertension. J Hypertens. 2001 Jul;19(7):1263-9. [PubMed:11446716 ]
  9. Park SY, Kim EJ, Shin HK, Kwon DY, Kim MS, Surh YJ, Park JH: Induction of apoptosis in HT-29 colon cancer cells by phloretin. J Med Food. 2007 Dec;10(4):581-6. [PubMed:18158826 ]
  10. Tombola F, Morbiato L, Del Giudice G, Rappuoli R, Zoratti M, Papini E: The Helicobacter pylori VacA toxin is a urea permease that promotes urea diffusion across epithelia. J Clin Invest. 2001 Sep;108(6):929-37. [PubMed:11560962 ]
  11. Pajor AM, Randolph KM, Kerner SA, Smith CD: Inhibitor binding in the human renal low- and high-affinity Na+/glucose cotransporters. J Pharmacol Exp Ther. 2008 Mar;324(3):985-91. Epub 2007 Dec 6. [PubMed:18063724 ]
  12. Rezk BM, Haenen GR, van der Vijgh WJ, Bast A: The antioxidant activity of phloretin: the disclosure of a new antioxidant pharmacophore in flavonoids. Biochem Biophys Res Commun. 2002 Jul 5;295(1):9-13. [PubMed:12083758 ]
  13. Pandey RP, Li TF, Kim EH, Yamaguchi T, Park YI, Kim JS, Sohng JK: Enzymatic synthesis of novel phloretin glucosides. Appl Environ Microbiol. 2013 Jun;79(11):3516-21. doi: 10.1128/AEM.00409-13. Epub 2013 Mar 29. [PubMed:23542617 ]

Enzymes

General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
Phloretin → 3,4,5-trihydroxy-6-{4-[3-oxo-3-(2,4,6-trihydroxyphenyl)propyl]phenoxy}oxane-2-carboxylic aciddetails
Phloretin → 6-{3,5-dihydroxy-2-[3-(4-hydroxyphenyl)propanoyl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Phloretin → 6-{3,5-dihydroxy-4-[3-(4-hydroxyphenyl)propanoyl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
General function:
sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:
SULT1A3
Uniprot ID:
P0DMM9
Molecular weight:
34195.96
Reactions
Phloretin → Dihydronaringenin-O-sulphatedetails