ChemSpider 2D Image | Phloretin | C15H14O5


  • Molecular FormulaC15H14O5
  • Average mass274.269 Da
  • Monoisotopic mass274.084137 Da
  • ChemSpider ID4624

More details:

Featured data source

Validated by Experts, Validated by Users, Non-Validated, Removed by Users

1-Propanone, 3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)- [ACD/Index Name]
200-488-7 [EINECS]
3-(4-Hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)-1-propanon [German] [ACD/IUPAC Name]
3-(4-Hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)-1-propanone [ACD/IUPAC Name]
3-(4-Hydroxyphényl)-1-(2,4,6-trihydroxyphényl)-1-propanone [French] [ACD/IUPAC Name]
3-(4-Hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)propan-1-one [ACD/IUPAC Name]
60-82-2 [RN]

Validated by Experts, Validated by Users, Non-Validated, Removed by Users

MFCD00002288 [DBID]
79310_FLUKA [DBID]
AIDS052153 [DBID]
AIDS-052153 [DBID]
C00774 [DBID]
CHEBI:17276 [DBID]
DivK1c_006429 [DBID]
EU-0101012 [DBID]
KBio1_001373 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      26-37 Alfa Aesar L10991
      36/37/38 Alfa Aesar L10991
      GHS07 Biosynth Q-100701
      H315; H319; H335 Biosynth Q-100701
      H315-H319-H335 Alfa Aesar L10991
      IRRITANT Alfa Aesar L10991
      IRRITANT Matrix Scientific 002894
      P261; P280; P302+P352; P304+P340; P305+P351+P338; P312 Biosynth Q-100701
      P261-P280-P305+P351+P338-P304+P340-P405-P501a Alfa Aesar L10991
      Warning Alfa Aesar L10991
      Warning Biosynth Q-100701
      WARNING: Irritates lungs, eyes, skin Alfa Aesar L10991
    • Target Organs:

      SGLT inhibitor TargetMol T2924
    • Chemical Class:

      A member of the class of dihydrochalcones that is dihydrochalcone substituted by hydroxy groups at positions 4, 2', 4' and 6'. ChEBI CHEBI:17276,
      chalcone Microsource [00300554]
      Dihydrochalcones Phenol-Explorer 108
      Flavonoids Phenol-Explorer 108
    • Drug Status:

      undetermined activity Microsource [00300554]
    • Compound Source:

      Found in free state in Helichrysum splendidum Zerenex Molecular [ZBioX-0253]
      Prunus spp Microsource [00300554]
    • Bio Activity:

      Antioxidant; Zerenex Molecular [ZBioX-0253]
      Biochemicals & small molecules/Antagonists & inhibitors Hello Bio HB0500
      Enzymes/Kinase/PKC Hello Bio HB0500
      Membrane Tranporter/Ion Channel MedChem Express HY-N0142
      Membrane Tranporter/Ion Channel; MedChem Express HY-N0142
      Membrane Transporter/Ion Channel TargetMol T2924
      Phloretin(NSC 407292; RJC 02792) is a dihydrochalcone, a type of natural phenols. MedChem Express, HY-N0142
      Phloretin(NSC 407292; RJC 02792) is a dihydrochalcone, a type of natural phenols. Phloretin inhibits the active transport of glucose into cells by SGLT1 and SGLT2.;IC50 Value: 49 +/- 12 microM [4];Target: SGLT1/2;In vitro: Phlorizin blocks glucose transport across the renal tubule at concentrations in renal blood and tissue in the range of 10-5 to 10-7 M [1]. PT significantly enhanced glycerol release and inhibited the adipogenesis-related transcription factors. PT also promoted phosphorylation of AMP-activated protein kinase and increased activity of adipose triglyceride lipase and hormone-sensitive lipase in 3T3-L1 cells [2]. Phloretin induced obvious cytotoxicity against BEL-7402 cells with IC50 of 89.23 microg/mL. The growth curve demonstrated decreased growth of the cells as phloretin concentration increased [3]. D-glucose-transport activity was observed with a Km for D-glucose of 3.4 +/- 0.2 mM (mean +/- S.E.M.) and was inhibited by cytochalasin B (IC50= 0.44 +/- 0.03 micr MedChem Express HY-N0142
      PKC inhibitor Hello Bio HB0500
      Protein kinase C (PKC) inhibitor. PGF<sub>2a</sub> receptor antagonist (IC<sub>50</sub> = 16 &micro;M). Inhibits GLUT2 glucose transport. Shows apoptotic, antitumor, antioxidant and immunomodulatory actions. Hello Bio HB0500
      SGLT MedChem Express HY-N0142
      SGLT1;SGLT2 TargetMol T2924
  • Gas Chromatography

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module

Density: 1.4±0.1 g/cm3
Boiling Point: 534.4±29.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.5 mmHg at 25°C
Enthalpy of Vaporization: 84.1±3.0 kJ/mol
Flash Point: 291.1±20.8 °C
Index of Refraction: 1.685
Molar Refractivity: 72.9±0.3 cm3
#H bond acceptors: 5
#H bond donors: 4
#Freely Rotating Bonds: 4
#Rule of 5 Violations: 0
ACD/LogP: 3.50
ACD/LogD (pH 5.5): 3.05
ACD/BCF (pH 5.5): 121.42
ACD/KOC (pH 5.5): 1071.89
ACD/LogD (pH 7.4): 2.53
ACD/BCF (pH 7.4): 36.66
ACD/KOC (pH 7.4): 323.64
Polar Surface Area: 98 Å2
Polarizability: 28.9±0.5 10-24cm3
Surface Tension: 74.9±3.0 dyne/cm
Molar Volume: 191.9±3.0 cm3

Predicted data is generated using the US Environmental Protection Agency’s EPISuite™

 Log Octanol-Water Partition Coef (SRC):
    Log Kow (KOWWIN v1.67 estimate) =  3.51

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  467.47  (Adapted Stein & Brown method)
    Melting Pt (deg C):  197.40  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.26E-011  (Modified Grain method)
    MP  (exp database):  263.5 dec deg C
    Subcooled liquid VP: 5.16E-009 mm Hg (25 deg C, Mod-Grain method)

 Water Solubility Estimate from Log Kow (WSKOW v1.41):
    Water Solubility at 25 deg C (mg/L):  66.62
       log Kow used: 3.51 (estimated)
       no-melting pt equation used
     Water Sol (Exper. database match) =  123 mg/L (16 deg C)
        Exper. Ref:  BEILSTEIN

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  960.61 mg/L
    Wat Sol (Exper. database match) =  123.00
       Exper. Ref:  BEILSTEIN

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.95E-016  atm-m3/mole
   Group Method:   7.39E-023  atm-m3/mole
 Henrys LC [VP/WSol estimate using EPI values]:  6.826E-014 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  3.51  (KowWin est)
  Log Kaw used:  -14.098  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  17.608
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.1417
   Biowin2 (Non-Linear Model)     :   0.9465
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.7212  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.5200  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.3138
   Biowin6 (MITI Non-Linear Model):   0.1709
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.0987
 Ready Biodegradability Prediction:   NO

Hydrocarbon Biodegradation (BioHCwin v1.01):
    Structure incompatible with current estimation method!

 Sorption to aerosols (25 Dec C)[AEROWIN v1.00]:
  Vapor pressure (liquid/subcooled):  6.88E-007 Pa (5.16E-009 mm Hg)
  Log Koa (Koawin est  ): 17.608
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  4.36 
       Octanol/air (Koa) model:  9.95E+004 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.994 
       Mackay model           :  0.997 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 205.0642 E-12 cm3/molecule-sec
      Half-Life =     0.052 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.626 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Reaction With Nitrate Radicals May Be Important!
   Fraction sorbed to airborne particulates (phi): 0.995 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  2.574E+004
      Log Koc:  4.411 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
    Rate constants can NOT be estimated for this structure!

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 1.159 (BCF = 14.43)
       log Kow used: 3.51 (estimated)

 Volatilization from Water:
    Henry LC:  1.95E-016 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 4.973E+012  hours   (2.072E+011 days)
    Half-Life from Model Lake : 5.425E+013  hours   (2.26E+012 days)

 Removal In Wastewater Treatment:
    Total removal:              13.26  percent
    Total biodegradation:        0.19  percent
    Total sludge adsorption:    13.08  percent
    Total to Air:                0.00  percent
      (using 10000 hr Bio P,A,S)

 Level III Fugacity Model:
           Mass Amount    Half-Life    Emissions
            (percent)        (hr)       (kg/hr)
   Air       2.04e-006       1.25         1000       
   Water     11.6            900          1000       
   Soil      87.6            1.8e+003     1000       
   Sediment  0.86            8.1e+003     0          
     Persistence Time: 1.84e+003 hr


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