ChemSpider 2D Image | latrunculin B | C20H29NO5S

latrunculin B

  • Molecular FormulaC20H29NO5S
  • Average mass395.513 Da
  • Monoisotopic mass395.176636 Da
  • ChemSpider ID10192733
  • Double-bond stereo - Double-bond stereo

    defined stereocentres - 5 of 5 defined stereocentres


More details:






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

(4R)-4-[(1R,8Z,10S,13R,15R)-15-Hydroxy-5,10-dimethyl-3-oxo-2,14-dioxabicyclo[11.3.1]heptadeca-4,8-dien-15-yl]-1,3-thiazolidin-2-on [German] [ACD/IUPAC Name]
(4R)-4-[(1R,8Z,10S,13R,15R)-15-Hydroxy-5,10-dimethyl-3-oxo-2,14-dioxabicyclo[11.3.1]heptadeca-4,8-dien-15-yl]-1,3-thiazolidin-2-one [ACD/IUPAC Name]
(4R)-4-[(1R,8Z,10S,13R,15R)-15-Hydroxy-5,10-diméthyl-3-oxo-2,14-dioxabicyclo[11.3.1]heptadéca-4,8-dién-15-yl]-1,3-thiazolidin-2-one [French] [ACD/IUPAC Name]
2-Thiazolidinone, 4-[(1R,8Z,10S,13R,15R)-15-hydroxy-5,10-dimethyl-3-oxo-2,14-dioxabicyclo[11.3.1]heptadeca-4,8-dien-15-yl]-, (4R)- [ACD/Index Name]
latrunculin B
(+)-latrunculin B
(4R)-4-[(1R,4S,5Z,9Z,13R,15R)-15-hydroxy-11-keto-4,9-dimethyl-12,16-dioxabicyclo[11.3.1]heptadeca-5,9-dien-15-yl]thiazolidin-2-one
(4R)-4-[(1R,4S,5Z,9Z,13R,15R)-15-hydroxy-4,9-dimethyl-11-oxo-12,16-dioxabicyclo[11.3.1]heptadeca-5,9-dien-15-yl]-1,3-thiazolidin-2-one
(4R)-4-[(1R,4S,5Z,9Z,13R,15R)-15-hydroxy-4,9-dimethyl-11-oxo-12,16-dioxabicyclo[11.3.1]heptadeca-5,9-dien-15-yl]-2-thiazolidinone
(4R)-4-[(1R,4S,5Z,9Z,13R,15R)-15-hydroxy-4,9-dimethyl-11-oxo-12,16-dioxabicyclo[11.3.1]heptadeca-5,9-dien-15-yl]thiazolidin-2-one
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

AIDS023786 [DBID]
AIDS-023786 [DBID]
LW7U308U7U [DBID]
NSC 339663 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Chemical Class:

      A macrolide consisting of a 14-membered bicyclic lactone attached to the rare 2-thiazolidinone moiety. It is obtained from the Red Sea sponge <ital>Latrunculia magnifica</ital>. ChEBI CHEBI:49703
    • Bio Activity:

      Actin Tocris Bioscience 3974
      Cytoskeleton and Motor Proteins Tocris Bioscience 3974
      Inhibitor of actin polymerization Tocris Bioscience 3974
      Inhibitor of actin polymerization. Interacts with G-actin in a 1:1 ratio to inhibit polymerization into F-actin in vitro (IC50 values are ~60 and ~900 nM in absence and presence of calf serum, respectively). Marine toxin. Tocris Bioscience 3974

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

Density: 1.2±0.1 g/cm3
Boiling Point:
Vapour Pressure:
Enthalpy of Vaporization:
Flash Point:
Index of Refraction: 1.533
Molar Refractivity: 104.2±0.3 cm3
#H bond acceptors: 6
#H bond donors: 2
#Freely Rotating Bonds: 1
#Rule of 5 Violations: 0
ACD/LogP: 3.51
ACD/LogD (pH 5.5): 2.75
ACD/BCF (pH 5.5): 72.19
ACD/KOC (pH 5.5): 744.60
ACD/LogD (pH 7.4): 2.75
ACD/BCF (pH 7.4): 72.19
ACD/KOC (pH 7.4): 744.53
Polar Surface Area: 110 Å2
Polarizability: 41.3±0.5 10-24cm3
Surface Tension: 41.4±3.0 dyne/cm
Molar Volume: 335.5±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) =  3.94

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  597.48  (Adapted Stein & Brown method)
    Melting Pt (deg C):  258.13  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  5.01E-016  (Modified Grain method)
    Subcooled liquid VP: 1.76E-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):  1.406
       log Kow used: 3.94 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  345.88 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   4.80E-016  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.854E-016 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  3.94  (KowWin est)
  Log Kaw used:  -13.707  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  17.647
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.2817
   Biowin2 (Non-Linear Model)     :   0.0647
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.1978  (months      )
   Biowin4 (Primary Survey Model) :   3.5365  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.1121
   Biowin6 (MITI Non-Linear Model):   0.0113
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.6456
 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):  2.35E-011 Pa (1.76E-013 mm Hg)
  Log Koa (Koawin est  ): 17.647
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  1.28E+005 
       Octanol/air (Koa) model:  1.09E+005 
   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 = 159.6312 E-12 cm3/molecule-sec
      Half-Life =     0.067 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.804 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    27.393749 E-17 cm3/molecule-sec
      Half-Life =     0.042 Days (at 7E11 mol/cm3)
      Half-Life =      1.004 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    :  161.3
      Log Koc:  2.208 

 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 = 2.335 (BCF = 216.1)
       log Kow used: 3.94 (estimated)

 Volatilization from Water:
    Henry LC:  4.8E-016 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 2.426E+012  hours   (1.011E+011 days)
    Half-Life from Model Lake : 2.646E+013  hours   (1.103E+012 days)

 Removal In Wastewater Treatment:
    Total removal:              27.40  percent
    Total biodegradation:        0.30  percent
    Total sludge adsorption:    27.10  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       0.0092          0.618        1000       
   Water     11.2            1.44e+003    1000       
   Soil      85.9            2.88e+003    1000       
   Sediment  2.89            1.3e+004     0          
     Persistence Time: 2.09e+003 hr




                    

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