ChemSpider 2D Image | (+)-brefeldin A | C16H24O4

(+)-brefeldin A

  • Molecular FormulaC16H24O4
  • Average mass280.359 Da
  • Monoisotopic mass280.167450 Da
  • ChemSpider ID4449949

  • Double-bond stereo - Double-bond stereo

    defined stereocentres - 5 of 5 defined stereocentres

More details:

Featured data source
The Merck Index Online

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

(+)-brefeldin A
(1R,2E,6S,10E,11aS,13S,14aR)-1,13-Dihydroxy-6-methyl-1,6,7,8,9,11a,12,13,14,14a-decahydro-4H-cyclopenta[f]oxacyclotridecin-4-on [German] [ACD/IUPAC Name]
(1R,2E,6S,10E,11aS,13S,14aR)-1,13-Dihydroxy-6-methyl-1,6,7,8,9,11a,12,13,14,14a-decahydro-4H-cyclopenta[f]oxacyclotridecin-4-one [ACD/IUPAC Name]
(1R,2E,6S,10E,11aS,13S,14aR)-1,13-Dihydroxy-6-méthyl-1,6,7,8,9,11a,12,13,14,14a-décahydro-4H-cyclopenta[f]oxacyclotridécin-4-one [French] [ACD/IUPAC Name]
(1R,6S,11aS,13S,14aR)-1,13-dihydroxy-6-methyl-1H,4H,6H,7H,8H,9H,11aH,12H,13H,14H,14aH-cyclopenta[f]oxacyclotridecan-4-one
1,6,7,8,9,11ab,12,13,14,14aa-Decahydro-1b,13a-dihydroxy-6b-methyl-4H-cyclopent(f)oxacyclotridecin-4-one
20350-15-6 [RN]
25191 [Beilstein]
4H-Cyclopent[f]oxacyclotridecin-4-one, 1,6,7,8,9,11a,12,13,14,14a-decahydro-1,13-dihydroxy-6-methyl-, (1R,2E,6S,10E,11aS,13S,14aR)- [ACD/Index Name]
ASCOTOXIN
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

25191; 5282047 [DBID]
B6542_SIGMA [DBID]
B7651_SIGMA [DBID]
  • Miscellaneous

    • Chemical Class:

      A metabolite from <ital>Penicillium brefeldianum</ital> that exhibits a wide range of antibiotic activity. ChEBI CHEBI:48080
      A metabolite from Penicillium brefeldianum that exhibits a wide range of antibiotic activity. ChEBI CHEBI:48080

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

Density: 1.1±0.1 g/cm3
Boiling Point: 492.7±45.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.8 mmHg at 25°C
Enthalpy of Vaporization: 87.5±6.0 kJ/mol
Flash Point: 180.8±22.2 °C
Index of Refraction: 1.513
Molar Refractivity: 76.1±0.3 cm3
#H bond acceptors: 4
#H bond donors: 2
#Freely Rotating Bonds: 0
#Rule of 5 Violations: 0
ACD/LogP: 1.61
ACD/LogD (pH 5.5): 1.60
ACD/BCF (pH 5.5): 9.76
ACD/KOC (pH 5.5): 177.74
ACD/LogD (pH 7.4): 1.60
ACD/BCF (pH 7.4): 9.76
ACD/KOC (pH 7.4): 177.74
Polar Surface Area: 67 Å2
Polarizability: 30.2±0.5 10-24cm3
Surface Tension: 40.1±3.0 dyne/cm
Molar Volume: 252.9±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) =  1.07

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  443.86  (Adapted Stein & Brown method)
    Melting Pt (deg C):  151.46  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.79E-010  (Modified Grain method)
    Subcooled liquid VP: 3.48E-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):  1946
       log Kow used: 1.07 (estimated)
       no-melting pt equation used
     Water Sol (Exper. database match) =  0.6 mg/L (26 deg C)
        Exper. Ref:  BEILSTEIN

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  2504.4 mg/L
    Wat Sol (Exper. database match) =  0.60
       Exper. Ref:  BEILSTEIN

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   7.48E-010  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  3.393E-014 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  1.07  (KowWin est)
  Log Kaw used:  -7.515  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  8.585
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.1057
   Biowin2 (Non-Linear Model)     :   0.9952
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   3.0397  (weeks       )
   Biowin4 (Primary Survey Model) :   3.9311  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.7301
   Biowin6 (MITI Non-Linear Model):   0.3906
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.4970
 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):  4.64E-007 Pa (3.48E-009 mm Hg)
  Log Koa (Koawin est  ): 8.585
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  6.47 
       Octanol/air (Koa) model:  9.44E-005 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.996 
       Mackay model           :  0.998 
       Octanol/air (Koa) model:  0.0075 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  96.8438 E-12 cm3/molecule-sec
      Half-Life =     0.110 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.325 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    21.137501 E-17 cm3/molecule-sec
      Half-Life =     0.054 Days (at 7E11 mol/cm3)
      Half-Life =      1.301 Hrs
   Fraction sorbed to airborne particulates (phi): 0.997 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  22.82
      Log Koc:  1.358 

 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 = 0.124 (BCF = 1.33)
       log Kow used: 1.07 (estimated)

 Volatilization from Water:
    Henry LC:  7.48E-010 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.311E+006  hours   (5.461E+004 days)
    Half-Life from Model Lake :  1.43E+007  hours   (5.957E+005 days)

 Removal In Wastewater Treatment:
    Total removal:               1.89  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.80  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       0.103           0.873        1000       
   Water     41.8            360          1000       
   Soil      58              720          1000       
   Sediment  0.085           3.24e+003    0          
     Persistence Time: 383 hr

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