ChemSpider 2D Image | multiplolide B | C14H18O6

multiplolide B

  • Molecular FormulaC14H18O6
  • Average mass282.289 Da
  • Monoisotopic mass282.110352 Da
  • ChemSpider ID9953199

  • Double-bond stereo - Double-bond stereo

    defined stereocentres - 3 of 5 defined stereocentres

More details:

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

(2E)-2-Buténoate de (4R,6R,7S,8E)-7-hydroxy-4-méthyl-2-oxo-3,11-dioxabicyclo[8.1.0]undéc-8-én-6-yle [French] [ACD/IUPAC Name]
(4R,6R,7S,8E)-7-Hydroxy-4-methyl-2-oxo-3,11-dioxabicyclo[8.1.0]undec-8-en-6-yl (2E)-2-butenoate [ACD/IUPAC Name]
(4R,6R,7S,8E)-7-Hydroxy-4-methyl-2-oxo-3,11-dioxabicyclo[8.1.0]undec-8-en-6-yl-(2E)-2-butenoat [German] [ACD/IUPAC Name]
multiplolide B
(4R,6R,7S,8E)-7-hydroxy-4-methyl-2-oxo-3,11-dioxabicyclo[8.1.0]undec-8-en-6-yl (2E)-but-2-enoate
(4R,6R,7S,8E)-7-hydroxy-4-methyl-2-oxo-3,11-dioxabicyclo[8.1.0]undec-8-en-6-yl (2E)-but-2-enoate (non-preferred name)
https://www.ebi.ac.uk/chembl/compoundreportcard/CHEMBL459619/
  • Miscellaneous

    • Chemical Class:

      A 10-membered lactone obtained from 10-methyl-9,10-dihydro-2<element>H</element>-oxecin-2-one by the epoxidation of the double bond at position 3-4 and <stereo>cis</stereo>-dihydroxylation of the doub le bond at position 7-8, with further acylation of the hydroxy group at position 8 by a but-2-enoyl group. Multiplolide B was first isolated from the fungus <ital>Xylaria multiplex</ital> BCC 1111. It shows antifungal activity against <ital>Candida albicans</ital>. The epoxide group has <stereo>cis</stereo>-configuration, but its configuration relative to the other substituents was not established . ChEBI CHEBI:66412
      A 10-membered lactone obtained from 10-methyl-9,10-dihydro-2H-oxecin-2-one by the epoxidation of the double bond at position 3-4 and cis-dihydroxylation of the double bond at position 7-8, with furthe r acylation of the hydroxy group at position 8 by a but-2-enoyl group. Multiplolide B was first isolated from the fungus Xylaria multiplex BCC 1111. It shows antifungal activity against Candida albica ns. The epoxide group has cis-configuration, but its configuration relative to the other substituents was not established. ChEBI CHEBI:66412

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

Density: 1.3±0.1 g/cm3
Boiling Point: 452.4±45.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.5 mmHg at 25°C
Enthalpy of Vaporization: 82.1±6.0 kJ/mol
Flash Point: 168.9±22.2 °C
Index of Refraction: 1.539
Molar Refractivity: 69.5±0.4 cm3
#H bond acceptors: 6
#H bond donors: 1
#Freely Rotating Bonds: 3
#Rule of 5 Violations: 0
ACD/LogP: 0.18
ACD/LogD (pH 5.5): 0.40
ACD/BCF (pH 5.5): 1.18
ACD/KOC (pH 5.5): 39.18
ACD/LogD (pH 7.4): 0.40
ACD/BCF (pH 7.4): 1.18
ACD/KOC (pH 7.4): 39.18
Polar Surface Area: 85 Å2
Polarizability: 27.5±0.5 10-24cm3
Surface Tension: 48.4±5.0 dyne/cm
Molar Volume: 221.9±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) =  0.53

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  418.59  (Adapted Stein & Brown method)
    Melting Pt (deg C):  142.73  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  3.38E-009  (Modified Grain method)
    Subcooled liquid VP: 5.24E-008 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):  1.766e+004
       log Kow used: 0.53 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  44964 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   3.09E-013  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  7.109E-014 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  0.53  (KowWin est)
  Log Kaw used:  -10.898  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  11.428
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.7729
   Biowin2 (Non-Linear Model)     :   0.9922
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   3.0071  (weeks       )
   Biowin4 (Primary Survey Model) :   4.0181  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.8299
   Biowin6 (MITI Non-Linear Model):   0.4769
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.6793
 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):  6.99E-006 Pa (5.24E-008 mm Hg)
  Log Koa (Koawin est  ): 11.428
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.429 
       Octanol/air (Koa) model:  0.0658 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.939 
       Mackay model           :  0.972 
       Octanol/air (Koa) model:  0.84 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  95.2434 E-12 cm3/molecule-sec [Cis-isomer]
      OVERALL OH Rate Constant =  97.9034 E-12 cm3/molecule-sec [Trans-isomer]
      Half-Life =    1.348 Hrs (12-hr day; 1.5E6 OH/cm3) [Cis-isomer]
      Half-Life =    1.311 Hrs (12-hr day; 1.5E6 OH/cm3) [Trans-isomer]
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    20.568750 E-17 cm3/molecule-sec [Cis-]
      OVERALL Ozone Rate Constant =    21.137501 E-17 cm3/molecule-sec [Trans-]
      Half-Life =     1.337 Hrs (at 7E11 mol/cm3) [Cis-isomer]
      Half-Life =     1.301 Hrs (at 7E11 mol/cm3) [Trans-isomer]
   Fraction sorbed to airborne particulates (phi): 0.956 (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]:
    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: 0.53 (estimated)

 Volatilization from Water:
    Henry LC:  3.09E-013 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 3.184E+009  hours   (1.326E+008 days)
    Half-Life from Model Lake : 3.473E+010  hours   (1.447E+009 days)

 Removal In Wastewater Treatment:
    Total removal:               1.86  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.77  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       0.000137        0.894        1000       
   Water     37.3            360          1000       
   Soil      62.6            720          1000       
   Sediment  0.0704          3.24e+003    0          
     Persistence Time: 590 hr

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