ChemSpider 2D Image | Loganin | C17H26O10

Loganin

  • Molecular FormulaC17H26O10
  • Average mass390.382 Da
  • Monoisotopic mass390.152588 Da
  • ChemSpider ID79111
  • defined stereocentres - 10 of 10 defined stereocentres


More details:






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

(-)-Loganin
(1S,4aS,6S,7R,7aS)-1-(β-D-Glucopyranosyloxy)-6-hydroxy-7-méthyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate de méthyle
(1S,4aS,6S,7R,7aS)-1-(β-D-Glucopyranosyloxy)-6-hydroxy-7-méthyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyrane-4-carboxylate de méthyle [French] [ACD/IUPAC Name]
(1S,4aS,6S,7R,7aS)-6-Hydroxy-7-méthyl-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxyméthyl)tétrahydro-2H-pyran-2-yl]oxy}-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate de méthyle
1-(b-D-Glucopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-6-hydroxy-7-methylcyclopenta[c]pyran-4-carboxylic Acid Methyl Ester
18524-94-2 [RN]
Cyclopenta[c]pyran-4-carboxylic acid, 1-(β-D-glucopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-6-hydroxy-7-methyl-, methyl ester, (1S,4aS,6S,7R,7aS)- [ACD/Index Name]
Loganin [Wiki]
Loganin, loganoside
Loganoside
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

55724 [DBID]
H7WJ16Q93C [DBID]
C01433 [DBID]
CHEBI:15771 [DBID]
DivK1c_006659 [DBID]
KBio1_001603 [DBID]
KBio2_001983 [DBID]
KBio2_004551 [DBID]
KBio2_007119 [DBID]
KBio3_002852 [DBID]
More...
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Target Organs:

      NF-??B inhibitor TargetMol T2759
    • Chemical Class:

      An iridoid monoterpenoid with formula C<smallsub>17</smallsub>H<smallsub>26</smallsub>O<smallsub>10</smallsub> that is isolated from several plant species and exhibits neuroprotective and anti-inflam matory properties. ChEBI CHEBI:15771
      An iridoid monoterpenoid with formula C17H26O10 that is isolated from several plant species and exhibits neuroprotective and anti-inflam; matory properties. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:15771
      An iridoid monoterpenoid with formula C17H26O10 that is isolated from several plant species and exhibits neuroprotective and anti-inflammatory properties. ChEBI CHEBI:15771
    • Compound Source:

      Calotropis gigantea PlantCyc LOGANIN
      Calycophyllum spruceanum (Rubiaceae) Susan Richardson [Structure found on ChemSpider, confirmed from ACD/Dictionary, ChEBI and ChEMBL]
      Camptotheca acuminata PlantCyc LOGANIN
      camptothecin biosynthesis PlantCyc LOGANIN
      Catharanthus roseus PlantCyc LOGANIN
      Isolated from a plant Susan Richardson [Structure found on ChemSpider, confirmed from ACD/Dictionary, ChEBI and ChEMBL]
      Linum usitatissimum PlantCyc LOGANIN
      secologanin and strictosidine biosynthesis PlantCyc LOGANIN
    • Bio Activity:

      7-deoxyloganin + NADPH + H+ + oxygen -> loganin + NADP+ + H2O PlantCyc LOGANIN
      7-deoxyloganin + NADPH + oxygen + H+ -> loganin + NADP+ + H2O PlantCyc LOGANIN
      Immunology/Inflammation TargetMol T2759
      loganin + NADPH + H+ + oxygen -> secologanin + NADP+ + 2 H2O PlantCyc LOGANIN
      loganin + NADPH + oxygen + H+ -> secologanin + NADP+ + 2 H2O PlantCyc LOGANIN
      Loganin, a major iridoid glycoside obtained from Corni fructus, has been shown to have anti-inflammatory and anti-shock effects. MedChem Express HY-N0512
      NF-??B TargetMol T2759
      Others MedChem Express HY-N0512
      S-adenosyl-L-methionine + loganate -> S-adenosyl-L-homocysteine + loganin PlantCyc LOGANIN

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module, version: 14.00

Density: 1.5±0.1 g/cm3
Boiling Point: 608.8±55.0 °C at 760 mmHg
Vapour Pressure: 0.0±4.0 mmHg at 25°C
Enthalpy of Vaporization: 103.7±6.0 kJ/mol
Flash Point: 217.9±25.0 °C
Index of Refraction: 1.600
Molar Refractivity: 88.8±0.4 cm3
#H bond acceptors: 10
#H bond donors: 5
#Freely Rotating Bonds: 5
#Rule of 5 Violations: 2
ACD/LogP: -2.73
ACD/LogD (pH 5.5): -2.03
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.89
ACD/LogD (pH 7.4): -2.03
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.89
Polar Surface Area: 155 Å2
Polarizability: 35.2±0.5 10-24cm3
Surface Tension: 72.2±5.0 dyne/cm
Molar Volume: 259.9±5.0 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) =  -2.35

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  558.86  (Adapted Stein & Brown method)
    Melting Pt (deg C):  240.09  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.01E-015  (Modified Grain method)
    Subcooled liquid VP: 2.13E-013 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):  3.536e+005
       log Kow used: -2.35 (estimated)
       no-melting pt equation used
     Water Sol (Exper. database match) =  1e+005 mg/L (20 deg C)
        Exper. Ref:  BEILSTEIN

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1e+006 mg/L
    Wat Sol (Exper. database match) =  100000.00
       Exper. Ref:  BEILSTEIN

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   8.35E-020  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.467E-021 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -2.35  (KowWin est)
  Log Kaw used:  -17.467  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  15.117
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.4874
   Biowin2 (Non-Linear Model)     :   0.0409
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   3.2505  (days-weeks  )
   Biowin4 (Primary Survey Model) :   4.1315  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.9052
   Biowin6 (MITI Non-Linear Model):   0.1034
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.9678
 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):  2.84E-011 Pa (2.13E-013 mm Hg)
  Log Koa (Koawin est  ): 15.117
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  1.06E+005 
       Octanol/air (Koa) model:  321 
   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 = 124.3798 E-12 cm3/molecule-sec
      Half-Life =     0.086 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.032 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     5.687500 E-17 cm3/molecule-sec
      Half-Life =     0.201 Days (at 7E11 mol/cm3)
      Half-Life =      4.836 Hrs
   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    :  10
      Log Koc:  1.000 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
  Total Kb for pH > 8 at 25 deg C :  2.069E-003  L/mol-sec
  Kb Half-Life at pH 8:      10.614  years  
  Kb Half-Life at pH 7:     106.143  years  

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 0.500 (BCF = 3.162)
       log Kow used: -2.35 (estimated)

 Volatilization from Water:
    Henry LC:  8.35E-020 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.385E+016  hours   (5.773E+014 days)
    Half-Life from Model Lake : 1.511E+017  hours   (6.297E+015 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       1.96e-005       1.45         1000       
   Water     34.5            208          1000       
   Soil      65.5            416          1000       
   Sediment  0.0596          1.87e+003    0          
     Persistence Time: 387 hr




                    

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