ChemSpider 2D Image | secologanin | C17H24O10

secologanin

  • Molecular FormulaC17H24O10
  • Average mass388.366 Da
  • Monoisotopic mass388.136932 Da
  • ChemSpider ID141670

  • defined stereocentres - 8 of 8 defined stereocentres

More details:

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

(-)-secologanin
(2S,3R,4S)-2-(β-D-Glucopyranosyloxy)-4-(2-oxoéthyl)-3-vinyl-3,4-dihydro-2H-pyrane-5-carboxylate de méthyle [French] [ACD/IUPAC Name]
19351-63-4 [RN]
2H-Pyran-5-carboxylic acid, 3-ethenyl-2-(β-D-glucopyranosyloxy)-3,4-dihydro-4-(2-oxoethyl)-, methyl ester, (2S,3R,4S)- [ACD/Index Name]
LONICEROSIDE
Methyl (2S,3R,4S)-2-(β-D-glucopyranosyloxy)-4-(2-oxoethyl)-3-vinyl-3,4-dihydro-2H-pyran-5-carboxylate [ACD/IUPAC Name]
methyl (2S,3R,4S)-3-ethenyl-2-(β-D-glucopyranosyloxy)-4-(2-oxoethyl)-3,4-dihydro-2H-pyran-5-carboxylate
Methyl (2S,3R,4S)-4-(2-oxoethyl)-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy}-3-vinyl-3,4-dihydro-2H-pyran-5-carboxylate
Methyl-(2S,3R,4S)-2-(β-D-glucopyranosyloxy)-4-(2-oxoethyl)-3-vinyl-3,4-dihydro-2H-pyran-5-carboxylat [German] [ACD/IUPAC Name]
MFCD16661163
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

1441446 [DBID]
50741_FLUKA [DBID]
C01852 [DBID]
CHEBI:18002 [DBID]
NSC 640525 [DBID]
  • Miscellaneous

    • Chemical Class:

      An iridoid monoterpenoid that is acetaldehyde in which on of the hydrogens of the methyl group has been replaced by a 2-(<stereo>beta</stereo>-<stereo>D</stereo>-glucopyranosyloxy)-3,4-dihydro-2H-pyra n-4-yl group which is substituted at positions 3 and 5 by a vinyl and a methoxycarbonyl group, respectively (the 2<stereo>S</stereo>,3<stereo>R</stereo>,4<stereo>S</stereo> stereoisomer). ChEBI CHEBI:18002
      An iridoid monoterpenoid that is acetaldehyde in which on of the hydrogens of the methyl group has been replaced by a 2-(beta-D-glucopyranosyloxy)-3,4-dihydro-2H-pyra; n-4-yl group which is substitute d at positions 3 and 5 by a vinyl and a methoxycarbonyl group, respectively (the 2S,3R,4S stereoisomer). ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:18002
      An iridoid monoterpenoid that is acetaldehyde in which on of the hydrogens of the methyl group has been replaced by a 2-(beta-D-glucopyranosyloxy)-3,4-dihydro-2H-pyran-4-yl group which is substituted at positions 3 and 5 by a vinyl and a methoxycarbonyl group, respectively (the 2S,3R,4S stereoisomer). ChEBI CHEBI:18002

    • Compound Source:

      Calotropis gigantea PlantCyc SECOLOGANIN-CPD
      Camptotheca acuminata PlantCyc SECOLOGANIN-CPD
      camptothecin biosynthesis PlantCyc SECOLOGANIN-CPD
      Catharanthus roseus PlantCyc SECOLOGANIN-CPD
      emetine biosynthesis PlantCyc SECOLOGANIN-CPD
      Linum usitatissimum PlantCyc SECOLOGANIN-CPD
      secologanin and strictosidine biosynthesis PlantCyc SECOLOGANIN-CPD

    • Bio Activity:

      dopamine + secologanin -> deacetylisoipecoside + H2O PlantCyc SECOLOGANIN-CPD
      loganin + NADPH + H+ + oxygen -> secologanin + NADP+ + 2 H2O PlantCyc SECOLOGANIN-CPD
      loganin + NADPH + oxygen + H+ -> secologanin + NADP+ + 2 H2O PlantCyc SECOLOGANIN-CPD
      tryptamine + secologanin -> 3-alpha(S)-strictosidine + H2O PlantCyc SECOLOGANIN-CPD

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

Density: 1.4±0.1 g/cm3
Boiling Point: 595.5±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±3.8 mmHg at 25°C
Enthalpy of Vaporization: 101.8±6.0 kJ/mol
Flash Point: 212.2±23.6 °C
Index of Refraction: 1.571
Molar Refractivity: 89.5±0.4 cm3
#H bond acceptors: 10
#H bond donors: 4
#Freely Rotating Bonds: 8
#Rule of 5 Violations: 1
ACD/LogP: -1.89
ACD/LogD (pH 5.5): -1.68
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 2.90
ACD/LogD (pH 7.4): -1.68
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 2.90
Polar Surface Area: 152 Å2
Polarizability: 35.5±0.5 10-24cm3
Surface Tension: 64.6±5.0 dyne/cm
Molar Volume: 272.4±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) =  -1.91

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  549.10  (Adapted Stein & Brown method)
    Melting Pt (deg C):  235.53  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.43E-015  (Modified Grain method)
    Subcooled liquid VP: 4.53E-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):  1.531e+005
       log Kow used: -1.91 (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:
       Acrylates
       Aldehydes
       Vinyl/Allyl Ethers

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.68E-021  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  8.111E-021 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -1.91  (KowWin est)
  Log Kaw used:  -18.960  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  17.050
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.6143
   Biowin2 (Non-Linear Model)     :   0.9496
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   3.1173  (weeks       )
   Biowin4 (Primary Survey Model) :   4.2016  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   1.1844
   Biowin6 (MITI Non-Linear Model):   0.5388
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.8837
 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):  6.04E-011 Pa (4.53E-013 mm Hg)
  Log Koa (Koawin est  ): 17.050
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  4.97E+004 
       Octanol/air (Koa) model:  2.75E+004 
   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 = 170.6892 E-12 cm3/molecule-sec
      Half-Life =     0.063 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.752 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     6.887500 E-17 cm3/molecule-sec
      Half-Life =     0.166 Days (at 7E11 mol/cm3)
      Half-Life =      3.993 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: -1.91 (estimated)

 Volatilization from Water:
    Henry LC:  2.68E-021 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 4.305E+017  hours   (1.794E+016 days)
    Half-Life from Model Lake : 4.697E+018  hours   (1.957E+017 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       1.94e-007       1.09         1000       
   Water     39              360          1000       
   Soil      60.9            720          1000       
   Sediment  0.0713          3.24e+003    0          
     Persistence Time: 579 hr

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