ChemSpider 2D Image | (+)-Cerulenin | C12H17NO3

(+)-Cerulenin

  • Molecular FormulaC12H17NO3
  • Average mass223.268 Da
  • Monoisotopic mass223.120850 Da
  • ChemSpider ID4445281
  • Double-bond stereo - Double-bond stereo

    defined stereocentres - 2 of 2 defined stereocentres


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(+)-Cerulenin
(2R,3S)-3-(1-oxonona-4,7-dienyl)-2-oxiranecarboxamide
(2R,3S)-3-[(4E,7E)-4,7-Nonadienoyl]-2-oxirancarboxamid [German] [ACD/IUPAC Name]
(2R,3S)-3-[(4E,7E)-4,7-Nonadienoyl]-2-oxirancarboximidsäure [German] [ACD/IUPAC Name]
(2R,3S)-3-[(4E,7E)-4,7-Nonadienoyl]-2-oxiranecarboxamide [ACD/IUPAC Name]
(2R,3S)-3-[(4E,7E)-4,7-Nonadienoyl]-2-oxiranecarboxamide [French] [ACD/IUPAC Name]
(2R,3S)-3-[(4E,7E)-4,7-Nonadienoyl]-2-oxiranecarboximidic acid [ACD/IUPAC Name]
(2R,3S)-3-[(4E,7E)-Nona-4,7-dienoyl]oxirane-2-carboxamide
[2R-[2a,3a(4E,7E)]]-3-(1-Oxo-4,7-nonadienyl)oxiranecarboxamide
17397-89-6 [RN]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

MF286Y830Q [DBID]
AIDS000236 [DBID]
AIDS-000236 [DBID]
Bio2_000478 [DBID]
Bio2_000958 [DBID]
C12058 [DBID]
KBio2_000616 [DBID]
KBio2_003184 [DBID]
KBio2_005752 [DBID]
KBio3_001091 [DBID]
More...
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      Harmful SynQuest 4348-1-19
    • Chemical Class:

      An epoxydodecadienamide isolated from several species, including <ital>Acremonium</ital>, <ital>Acrocylindrum</ital> and <ital>Helicoceras</ital>. It inhibits the biosynthesis of several lipids by int erfering with enzyme function. ChEBI CHEBI:171741

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

Density: 1.1±0.1 g/cm3
Boiling Point: 456.1±45.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.1 mmHg at 25°C
Enthalpy of Vaporization: 71.6±3.0 kJ/mol
Flash Point: 241.1±25.0 °C
Index of Refraction: 1.529
Molar Refractivity: 60.7±0.3 cm3
#H bond acceptors: 4
#H bond donors: 2
#Freely Rotating Bonds: 7
#Rule of 5 Violations: 0
ACD/LogP: 0.94
ACD/LogD (pH 5.5): 0.49
ACD/BCF (pH 5.5): 1.38
ACD/KOC (pH 5.5): 43.92
ACD/LogD (pH 7.4): 0.49
ACD/BCF (pH 7.4): 1.38
ACD/KOC (pH 7.4): 43.93
Polar Surface Area: 73 Å2
Polarizability: 24.1±0.5 10-24cm3
Surface Tension: 46.1±3.0 dyne/cm
Molar Volume: 196.7±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) =  1.74

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  384.60  (Adapted Stein & Brown method)
    Melting Pt (deg C):  142.12  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  4.27E-006  (Modified Grain method)
    MP  (exp database):  93.5 deg C
    Subcooled liquid VP: 1.96E-005 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):  1079
       log Kow used: 1.74 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1.6015e+005 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Epoxides

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   3.46E-012  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.163E-009 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  1.74  (KowWin est)
  Log Kaw used:  -9.849  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  11.589
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.6193
   Biowin2 (Non-Linear Model)     :   0.6203
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.9187  (weeks       )
   Biowin4 (Primary Survey Model) :   3.9681  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.4920
   Biowin6 (MITI Non-Linear Model):   0.2414
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.9155
 Ready Biodegradability Prediction:   NO

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

 Sorption to aerosols (25 Dec C)[AEROWIN v1.00]:
  Vapor pressure (liquid/subcooled):  0.00261 Pa (1.96E-005 mm Hg)
  Log Koa (Koawin est  ): 11.589
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.00115 
       Octanol/air (Koa) model:  0.0953 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.0398 
       Mackay model           :  0.0841 
       Octanol/air (Koa) model:  0.884 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 121.7588 E-12 cm3/molecule-sec [Cis-isomer]
      OVERALL OH Rate Constant = 136.9588 E-12 cm3/molecule-sec [Trans-isomer]
      Half-Life =    1.054 Hrs (12-hr day; 1.5E6 OH/cm3) [Cis-isomer]
      Half-Life =    0.937 Hrs (12-hr day; 1.5E6 OH/cm3) [Trans-isomer]
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    26.000000 E-17 cm3/molecule-sec [Cis-]
      OVERALL Ozone Rate Constant =    40.000000 E-17 cm3/molecule-sec [Trans-]
      Half-Life =     1.058 Hrs (at 7E11 mol/cm3) [Cis-isomer]
      Half-Life =     0.688 Hrs (at 7E11 mol/cm3) [Trans-isomer]
   Reaction With Nitrate Radicals May Be Important!
   Fraction sorbed to airborne particulates (phi): 0.062 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  23.73
      Log Koc:  1.375 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
  Total Ka (acid-catalyzed) at 25 deg C :  4.581E-009  L/mol-sec
  Ka Half-Life at pH 7: 4.794E+007  years  

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 0.640 (BCF = 4.368)
       log Kow used: 1.74 (estimated)

 Volatilization from Water:
    Henry LC:  3.46E-012 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 2.528E+008  hours   (1.054E+007 days)
    Half-Life from Model Lake : 2.758E+009  hours   (1.149E+008 days)

 Removal In Wastewater Treatment:
    Total removal:               2.07  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.97  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       7.04e-005       0.704        1000       
   Water     26              360          1000       
   Soil      74              720          1000       
   Sediment  0.072           3.24e+003    0          
     Persistence Time: 679 hr




                    

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