ChemSpider 2D Image | (-)-salinosporamide A | C15H20ClNO4

(-)-salinosporamide A

  • Molecular FormulaC15H20ClNO4
  • Average mass313.777 Da
  • Monoisotopic mass313.108093 Da
  • ChemSpider ID9522473

  • 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

(-)-salinosporamide A
(1R,4R,5S)-4-(2-Chlorethyl)-1-[(S)-(1S)-2-cyclohexen-1-yl(hydroxy)methyl]-5-methyl-6-oxa-2-azabicyclo[3.2.0]heptan-3,7-dion [German] [ACD/IUPAC Name]
(1R,4R,5S)-4-(2-Chloroethyl)-1-[(S)-(1S)-2-cyclohexen-1-yl(hydroxy)methyl]-5-methyl-6-oxa-2-azabicyclo[3.2.0]heptane-3,7-dione [ACD/IUPAC Name]
(1R,4R,5S)-4-(2-Chloroéthyl)-1-[(S)-(1S)-2-cyclohexén-1-yl(hydroxy)méthyl]-5-méthyl-6-oxa-2-azabicyclo[3.2.0]heptane-3,7-dione [French] [ACD/IUPAC Name]
(1R,4R,5S)-4-(2-chloroethyl)-1-[(S)-(1S)-cyclohex-2-en-1-yl(hydroxy)methyl]-3-hydroxy-5-methyl-6-oxa-2-azabicyclo[3.2.0]hept-2-en-7-one
(1R,4R,5S)-4-(2-chloroethyl)-1-[(S)-[(1S)-cyclohex-2-en-1-yl](hydroxy)methyl]-5-methyl-6-oxa-2-azabicyclo[3.2.0]heptane-3,7-dione
437742-34-2 [RN]
6-Oxa-2-azabicyclo[3.2.0]heptane-3,7-dione, 4-(2-chloroethyl)-1-[(S)-(1S)-2-cyclohexen-1-ylhydroxymethyl]-5-methyl-, (1R,4R,5S)- [ACD/Index Name]
703P9YDP7F
marizomib [INN] [USAN]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

9205 [DBID]
nchembio.2007.56-comp1 [DBID]
  • Miscellaneous

    • Chemical Class:

      A salinosporamide in which the core (1<stereo>R</stereo>)-6-oxa-2-azabicyclo[3.2.0]heptane-3,7-dione skeleton is substituted at positions 1, 4, and 5 by (1<stereo>S</stereo>)-cyclohex-2-en-1-yl(hydrox y)methyl, 2-chloroethyl, and methyl groups, respectively (the 1<stereo>R</stereo>,4<stereo>R</stereo>,5<stereo>S</stereo> diastereoisomer). A potent proteasome inhibitor, it has attracted interest for potential use in the treatment of various cancers. ChEBI CHEBI:48045
      A salinosporamide in which the core (1R)-6-oxa-2-azabicyclo[3.2.0]heptane-3,7-dione skeleton is substituted at positions 1, 4, and 5 by (1S)-cyclohex-2-en-1-yl(hydrox; y)methyl, 2-chloroethyl, and met hyl groups, respectively (the 1R,4R,5S diastereoisomer). A potent proteasome inhibitor, it has attracted interest for; potential use in the treatment of various cancers. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:48045
      A salinosporamide in which the core (1R)-6-oxa-2-azabicyclo[3.2.0]heptane-3,7-dione skeleton is substituted at positions 1, 4, and 5 by (1S)-cyclohex-2-en-1-yl(hydroxy)methyl, 2-chloroethyl, and methy l groups, respectively (the 1R,4R,5S diastereoisomer). A potent proteasome inhibitor, it has attracted interest for potential use in the treatment of various cancers. ChEBI CHEBI:48045

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

Density: 1.3±0.1 g/cm3
Boiling Point: 547.0±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±3.3 mmHg at 25°C
Enthalpy of Vaporization: 95.0±6.0 kJ/mol
Flash Point: 284.6±30.1 °C
Index of Refraction: 1.571
Molar Refractivity: 76.4±0.3 cm3
#H bond acceptors: 5
#H bond donors: 2
#Freely Rotating Bonds: 4
#Rule of 5 Violations: 0
ACD/LogP: 0.28
ACD/LogD (pH 5.5): 0.76
ACD/BCF (pH 5.5): 2.22
ACD/KOC (pH 5.5): 61.52
ACD/LogD (pH 7.4): 0.76
ACD/BCF (pH 7.4): 2.22
ACD/KOC (pH 7.4): 61.52
Polar Surface Area: 76 Å2
Polarizability: 30.3±0.5 10-24cm3
Surface Tension: 54.2±3.0 dyne/cm
Molar Volume: 232.7±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) =  0.65

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  509.38  (Adapted Stein & Brown method)
    Melting Pt (deg C):  216.98  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  8.66E-013  (Modified Grain method)
    Subcooled liquid VP: 9.65E-011 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):  2840
       log Kow used: 0.65 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  4692.8 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.93E-014  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.259E-016 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  0.65  (KowWin est)
  Log Kaw used:  -12.103  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  12.753
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.6620
   Biowin2 (Non-Linear Model)     :   0.7581
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.1543  (months      )
   Biowin4 (Primary Survey Model) :   3.5514  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.6915
   Biowin6 (MITI Non-Linear Model):   0.3205
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.7319
 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):  1.29E-008 Pa (9.65E-011 mm Hg)
  Log Koa (Koawin est  ): 12.753
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  233 
       Octanol/air (Koa) model:  1.39 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  1 
       Mackay model           :  1 
       Octanol/air (Koa) model:  0.991 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  82.5465 E-12 cm3/molecule-sec
      Half-Life =     0.130 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.555 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    20.000000 E-17 cm3/molecule-sec
      Half-Life =     0.057 Days (at 7E11 mol/cm3)
      Half-Life =      1.375 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    :  144.9
      Log Koc:  2.161 

 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: 0.65 (estimated)

 Volatilization from Water:
    Henry LC:  1.93E-014 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 5.374E+010  hours   (2.239E+009 days)
    Half-Life from Model Lake : 5.862E+011  hours   (2.443E+010 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       0.00269         0.954        1000       
   Water     46.7            1.44e+003    1000       
   Soil      53.2            2.88e+003    1000       
   Sediment  0.0949          1.3e+004     0          
     Persistence Time: 1.19e+003 hr

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