ChemSpider 2D Image | Latrunculin A | C22H31NO5S

Latrunculin A

  • Molecular FormulaC22H31NO5S
  • Average mass421.550 Da
  • Monoisotopic mass421.192291 Da
  • ChemSpider ID393069
  • Double-bond stereo - Double-bond stereo

    defined stereocentres - 5 of 5 defined stereocentres


More details:



Featured data source



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

(4R)-4-[(1R,4Z,8E,10Z,12S,15R,17R)-17-Hydroxy-5,12-dimethyl-3-oxo-2,16-dioxabicyclo[13.3.1]nonadeca-4,8,10-trien-17-yl]-1,3-thiazolidin-2-on [German] [ACD/IUPAC Name]
(4R)-4-[(1R,4Z,8E,10Z,12S,15R,17R)-17-Hydroxy-5,12-dimethyl-3-oxo-2,16-dioxabicyclo[13.3.1]nonadeca-4,8,10-trien-17-yl]-1,3-thiazolidin-2-one [ACD/IUPAC Name]
(4R)-4-[(1R,4Z,8E,10Z,12S,15R,17R)-17-Hydroxy-5,12-diméthyl-3-oxo-2,16-dioxabicyclo[13.3.1]nonadéca-4,8,10-trién-17-yl]-1,3-thiazolidin-2-one [French] [ACD/IUPAC Name]
2-Thiazolidinone, 4-((1R,4Z,8E,10Z,12S,15R,17R)-17-hydroxy-5,12-dimethyl-3-oxo-2,16-dioxabicyclo(13.3.1)nonadeca-4,8,10-trien-17-yl)-, (4R)-
2-Thiazolidinone, 4-[(1R,4Z,8E,10Z,12S,15R,17R)-17-hydroxy-5,12-dimethyl-3-oxo-2,16-dioxabicyclo[13.3.1]nonadeca-4,8,10-trien-17-yl]-, (4R)- [ACD/Index Name]
76343-93-6 [RN]
Latrunculin A
latrunculin A (incomplete stereochemistry)
(+)-latrunculin A
(4R)-[(1R,4Z,8E,10Z,12S,15R,17R)-17-hydroxy-5,12-dimethyl-3-oxo-2,16-dioxabicyclo[13.3.1]nonadeca-4,8,10-trien-17-yl]-2-thiazolidinone
More...

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

SRQ9WWM084 [DBID]
AIDS112130 [DBID]
AIDS-112130 [DBID]
CCRIS 4693 [DBID]
NSC 613011 [DBID]
NSC613011 [DBID]
UNII:SRQ9WWM084 [DBID]
UNII-SRQ9WWM084 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Chemical Class:

      A bicyclic macrolide natural product consisting of a 16-membered bicyclic lactone attached to the rare 2-thiazolidinone moiety. It is obtained from the Red Sea sponge <ital>Latrunculia magnifica</ital > and from the Fiji Islands sponge <ital>Cacospongia mycofijiensis</ital>. Latrunculin A inhibits actin polymerisation, microfilament organsation and microfilament-mediated processes. ChEBI CHEBI:69136
    • Bio Activity:

      Actin Tocris Bioscience 3973
      Cytoskeleton and Motor Proteins Tocris Bioscience 3973
      Inhibitor of actin assembly and polymerization Tocris Bioscience 3973
      Reversible inhibitor of actin assembly; blocks actin adenine nucleotide exchange. Complexes with actin in vitro and interacts with actin monomers only, unlike cytochalasins. Prevents actin repolymeriz ation into filaments and disrupts the actin cytoskeleton. Tocris Bioscience 3973
      Reversible inhibitor of actin assembly; blocks actin adenine nucleotide exchange. Complexes with actin in vitro and interacts with actin monomers only, unlike cytochalasins. Prevents actin repolymerization into filaments and disrupts the actin cytoskeleton. Tocris Bioscience 3973

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: 113.0±0.3 cm3
#H bond acceptors: 6
#H bond donors: 2
#Freely Rotating Bonds: 1
#Rule of 5 Violations: 0
ACD/LogP: 4.14
ACD/LogD (pH 5.5): 3.22
ACD/BCF (pH 5.5): 166.02
ACD/KOC (pH 5.5): 1351.47
ACD/LogD (pH 7.4): 3.22
ACD/BCF (pH 7.4): 166.01
ACD/KOC (pH 7.4): 1351.34
Polar Surface Area: 110 Å2
Polarizability: 44.8±0.5 10-24cm3
Surface Tension: 40.5±3.0 dyne/cm
Molar Volume: 364.3±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) =  4.71

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  624.34  (Adapted Stein & Brown method)
    Melting Pt (deg C):  270.68  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  4.96E-017  (Modified Grain method)
    Subcooled liquid VP: 2.5E-014 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):  0.2143
       log Kow used: 4.71 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  68.772 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   6.07E-016  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.284E-016 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  4.71  (KowWin est)
  Log Kaw used:  -13.605  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  18.315
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.2693
   Biowin2 (Non-Linear Model)     :   0.0456
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.1403  (months      )
   Biowin4 (Primary Survey Model) :   3.4989  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.0470
   Biowin6 (MITI Non-Linear Model):   0.0057
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.7926
 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):  3.33E-012 Pa (2.5E-014 mm Hg)
  Log Koa (Koawin est  ): 18.315
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  9E+005 
       Octanol/air (Koa) model:  5.07E+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 = 245.2312 E-12 cm3/molecule-sec
      Half-Life =     0.044 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.523 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    39.393749 E-17 cm3/molecule-sec
      Half-Life =     0.029 Days (at 7E11 mol/cm3)
      Half-Life =     41.891 Min
   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    :  548.6
      Log Koc:  2.739 

 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 = 2.925 (BCF = 842.2)
       log Kow used: 4.71 (estimated)

 Volatilization from Water:
    Henry LC:  6.07E-016 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River:  1.98E+012  hours   (8.252E+010 days)
    Half-Life from Model Lake :  2.16E+013  hours   (9.002E+011 days)

 Removal In Wastewater Treatment:
    Total removal:              66.44  percent
    Total biodegradation:        0.60  percent
    Total sludge adsorption:    65.84  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       0.00954         0.419        1000       
   Water     10.5            1.44e+003    1000       
   Soil      72.6            2.88e+003    1000       
   Sediment  16.9            1.3e+004     0          
     Persistence Time: 1.99e+003 hr




                    

Click to predict properties on the Chemicalize site





Feedback Form