ChemSpider 2D Image | vitexin | C21H20O10

vitexin

  • Molecular FormulaC21H20O10
  • Average mass432.378 Da
  • Monoisotopic mass432.105652 Da
  • ChemSpider ID4444098
  • defined stereocentres - 5 of 5 defined stereocentres


More details:






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

(1S)-1,5-Anhydro-1-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-8-yl]-D-glucitol [ACD/IUPAC Name]
(1S)-1,5-Anhydro-1-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-8-yl]-D-glucitol [German] [ACD/IUPAC Name]
(1S)-1,5-Anhydro-1-[5,7-dihydroxy-2-(4-hydroxyphényl)-4-oxo-4H-chromén-8-yl]-D-glucitol [French] [ACD/IUPAC Name]
222-963-8 [EINECS]
3681-93-4 [RN]
4H-1-Benzopyran-4-one, 5,7-dihydroxy-8-β-D- glucopyranosyl-2-(4-hydroxyphenyl)-
4H-1-Benzopyran-4-one, 5,7-dihydroxy-8-β-D-glucopyranosyl-2-(4-hydroxyphenyl)-
4H-1-Benzopyran-4-one, 8-β-D-glucopyranosyl-5,7-dihydroxy-2-(4-hydroxyphenyl)-
4H-1-Benzopyran-4-one, 8-β-D-glucopyranosyl-5,7-dihydroxy-2-(4-hydroxyphenyl)-
5,7-Dihydroxy-2-(4-hydroxyphenyl)-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]-4H-chromen-4-on
More...

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

49513_FLUKA [DBID]
AIDS026705 [DBID]
AIDS-026705 [DBID]
C01460 [DBID]
CHEBI:16954 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      P261; P262 Biosynth Q-100437
    • Chemical Class:

      An apigenin flavone glycoside, which is found in the passion flower, bamboo leaves and pearl millet ChEBI CHEBI:16954, https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:16954
    • Compound Source:

      Aegilops tauschii PlantCyc VITEXIN
      Ananas comosus PlantCyc VITEXIN
      Brachypodium distachyon PlantCyc VITEXIN
      Camptotheca acuminata PlantCyc VITEXIN
      Citrus clementina PlantCyc VITEXIN
      Citrus sinensis PlantCyc VITEXIN
      flavonoid di-C-glucosylation PlantCyc VITEXIN
      Glycine max PlantCyc VITEXIN
      Gossypium raimondii PlantCyc VITEXIN
      Hordeum vulgare subsp. vulgare PlantCyc VITEXIN
      Isolated from a plant Susan Richardson [Structure found in ChEMBL, confirmed from ChEBI and DOI: 10.1590/S0100-40422009000500005]
      Leersia perrieri PlantCyc VITEXIN
      Linum usitatissimum PlantCyc VITEXIN
      Miscanthus sinensis PlantCyc VITEXIN
      naringenin C-glucosylation PlantCyc VITEXIN
      Oryza brachyantha PlantCyc VITEXIN
      Oryza glaberrima PlantCyc VITEXIN
      Oryza punctata PlantCyc VITEXIN
      Oryza rufipogon PlantCyc VITEXIN
      Oryza sativa Japonica Group PlantCyc VITEXIN
      Panicum hallii PlantCyc VITEXIN
      Panicum virgatum PlantCyc VITEXIN
      Piper umbellata (Piperaceae) Susan Richardson [Structure found in ChEMBL, confirmed from ChEBI and DOI: 10.1590/S0100-40422009000500005]
      Setaria italica PlantCyc VITEXIN
      Setaria viridis PlantCyc VITEXIN
      Sorghum bicolor PlantCyc VITEXIN
      Triticum aestivum PlantCyc VITEXIN
      Triticum urartu PlantCyc VITEXIN
      vitexin and derivatives biosynthesis PlantCyc VITEXIN
      Zea mays subsp. mays PlantCyc VITEXIN
    • Bio Activity:

      α-Glucosidase inhibitor Hello Bio [HB4123]
      3-C-glucosyl-2,4,4',6-tetrahydroxydibenzoylmethane -> vitexin + H2O PlantCyc VITEXIN
      alpha-Glucosidase inhibitor. Antioxidant. HIF-1 alpha inhibitor. Anti-metastatic. Apoptosis inducer. Tumor suppressor. Adipogenesis inhibitor. Inhibits SIRT6 in vitro. Inhibits polyubiquitin synthesis by the ubiquitin-conjugating enzyme E2-25K. Cardioprotective. Anti-inflammatory. Shows analgesic effect by targeting TRPV1 channel activity. Neuroprotective. Inhibits NMDA receptors. Hello Bio [HB4123]
      apigenin + UDP-alpha-D-glucose -> vitexin + UDP + H+ PlantCyc VITEXIN
      Biochemicals & small molecules/Antagonists & inhibitors Hello Bio [HB4123]
      Enzymes/Glycosylase/Glucosidase/α Hello Bio [HB4123]
      UDP-alpha-D-glucose + vitexin -> vitexin 2''-O-beta-D-glucoside + UDP + H+ PlantCyc VITEXIN
      vitexin + UDP-beta-L-rhamnose -> vitexin 2''-O-beta-L-rhamnoside + UDP + H+ PlantCyc VITEXIN

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

Density: 1.7±0.1 g/cm3
Boiling Point: 767.7±60.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.7 mmHg at 25°C
Enthalpy of Vaporization: 117.3±3.0 kJ/mol
Flash Point: 273.1±26.4 °C
Index of Refraction: 1.743
Molar Refractivity: 103.7±0.3 cm3
#H bond acceptors: 10
#H bond donors: 7
#Freely Rotating Bonds: 3
#Rule of 5 Violations: 2
ACD/LogP: 1.28
ACD/LogD (pH 5.5): 0.85
ACD/BCF (pH 5.5): 2.45
ACD/KOC (pH 5.5): 61.37
ACD/LogD (pH 7.4): -0.65
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.95
Polar Surface Area: 177 Å2
Polarizability: 41.1±0.5 10-24cm3
Surface Tension: 99.1±3.0 dyne/cm
Molar Volume: 256.3±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) =  -1.68

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  730.89  (Adapted Stein & Brown method)
    Melting Pt (deg C):  320.45  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.22E-022  (Modified Grain method)
    Subcooled liquid VP: 2.6E-019 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):  1.985e+005
       log Kow used: -1.68 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1e+006 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Phenols
       Vinyl/Allyl Ketones
       Vinyl/Allyl Ethers
       Vinyl/Allyl Alcohols

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   5.97E-024  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  3.497E-028 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -1.68  (KowWin est)
  Log Kaw used:  -21.612  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  19.932
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.9220
   Biowin2 (Non-Linear Model)     :   0.0559
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   3.2200  (weeks       )
   Biowin4 (Primary Survey Model) :   3.9986  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.7344
   Biowin6 (MITI Non-Linear Model):   0.0755
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.5015
 Ready Biodegradability Prediction:   YES

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

 Sorption to aerosols (25 Dec C)[AEROWIN v1.00]:
  Vapor pressure (liquid/subcooled):  3.47E-017 Pa (2.6E-019 mm Hg)
  Log Koa (Koawin est  ): 19.932
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  8.65E+010 
       Octanol/air (Koa) model:  2.1E+007 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  1 
       Mackay model           :  1 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 281.3175 E-12 cm3/molecule-sec
      Half-Life =     0.038 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    27.375 Min
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    65.455002 E-17 cm3/molecule-sec
      Half-Life =     0.018 Days (at 7E11 mol/cm3)
      Half-Life =     25.212 Min
   Reaction With Nitrate Radicals May Be Important!
   Fraction sorbed to airborne particulates (phi): 1 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  14.2
      Log Koc:  1.152 

 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 = 0.500 (BCF = 3.162)
       log Kow used: -1.68 (estimated)

 Volatilization from Water:
    Henry LC:  5.97E-024 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 2.039E+020  hours   (8.497E+018 days)
    Half-Life from Model Lake : 2.225E+021  hours   (9.269E+019 days)

 Removal In Wastewater Treatment:
    Total removal:               1.85  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.75  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       0.0012          0.288        1000       
   Water     39.2            360          1000       
   Soil      60.7            720          1000       
   Sediment  0.0718          3.24e+003    0          
     Persistence Time: 568 hr




                    

Click to predict properties on the Chemicalize site






Advertisement