ChemSpider 2D Image | (+)-Ophiobolin A | C25H36O4

(+)-Ophiobolin A

  • Molecular FormulaC25H36O4
  • Average mass400.551 Da
  • Monoisotopic mass400.261353 Da
  • ChemSpider ID4444744

  • Double-bond stereo - Double-bond stereo

    defined stereocentres - 8 of 8 defined stereocentres

More details:

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

(+)-Ophiobolin A
(2'S,3'S,3aR,5'R,6aS,9R,9aS,10aR)-1,3a,4,4',5',6a,7,8,9,9a,10,10a-dodecahydro-9-hydroxy-3',9,10a-trimethyl-5'-spiro[dicyclopenta[a,d]cyclooctene-3(2H),2'(3'H)-furan]-6-carboxaldehyde
(7E,18R)-3-Hydroxy-5-oxo-14,18-epoxyophiobola-7,19-dien-25-al [ACD/IUPAC Name]
(7E,18R)-3-Hydroxy-5-oxo-14,18-epoxyophiobola-7,19-dien-25-al [German] [ACD/IUPAC Name]
(7E,18R)-3-Hydroxy-5-oxo-14,18-époxyophiobola-7,19-dién-25-al [French] [ACD/IUPAC Name]
4611-05-6 [RN]
Ophiobolin A
RL1576000
Spiro[dicyclopenta[a,d]cyclooctene-3(2H),2'(3'H)-furan]-6-carboxaldehyde, 1,3a,4,4',5',6a,7,8,9,9a,10,10a-dodecahydro-9-hydroxy-3',9,10a-trimethyl-5'-(2-methyl-1-propen-1-yl)-7-oxo-, (3S,3'S,3aR,5E,5' R,6aS,9R,9aS,10aR)- [ACD/Index Name]
spiro[dicyclopenta[a,d]cyclooctene-3(2H),2'(3'H)-furan]-6-carboxaldehyde, 1,3a,4,4',5',6a,7,8,9,9a,10,10a-dodecahydro-9-hydroxy-3',9,10a-trimethyl-5'-(2-methyl-1-propen-1-yl)-7-oxo-, (3S,3'S,3aR,5E,5'R,6aS,9R,9aS,10aR)-
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

C09145 [DBID]
CHEBI:7777 [DBID]
NSC 114340 [DBID]
NSC-114340 [DBID]
O1380_SIGMA [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Chemical Class:

      A sesterterpenoid that is ophiobolane with a hydroxy group at position 3, oxo groups at positions 5 and 25, double bonds at positions 7-8 and 19-20, and an oxygen link between positions 14 and 18. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:7777, CHEBI:7777

    • Bio Activity:

      Biochemicals & small molecules/Antagonists & inhibitors Hello Bio HB0474
      Irreversible calmodulin antagonist Hello Bio HB0474
      Irreversible calmodulin antagonist that reacts with lysine residues (IC<sub>50</sub> 0.87-3.7 &micro;M). Also inhibits calcium-dependent human growth hormone (hGH) release (approx K<sub>i</sub> = 10 &micro;M). A membrane permeable fungal metabolite and a phytotoxin. Displays antitumor and apoptotic inducing properties. Hello Bio HB0474
      Proteins - Other/Calmodulin Hello Bio HB0474

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

Density: 1.1±0.1 g/cm3
Boiling Point: 539.4±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±3.3 mmHg at 25°C
Enthalpy of Vaporization: 93.9±6.0 kJ/mol
Flash Point: 177.8±23.6 °C
Index of Refraction: 1.554
Molar Refractivity: 112.6±0.4 cm3
#H bond acceptors: 4
#H bond donors: 1
#Freely Rotating Bonds: 2
#Rule of 5 Violations: 0
ACD/LogP: 3.75
ACD/LogD (pH 5.5): 3.63
ACD/BCF (pH 5.5): 336.03
ACD/KOC (pH 5.5): 2238.64
ACD/LogD (pH 7.4): 3.63
ACD/BCF (pH 7.4): 336.03
ACD/KOC (pH 7.4): 2238.63
Polar Surface Area: 64 Å2
Polarizability: 44.7±0.5 10-24cm3
Surface Tension: 45.3±5.0 dyne/cm
Molar Volume: 351.3±5.0 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) =  4.55

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  487.00  (Adapted Stein & Brown method)
    Melting Pt (deg C):  206.52  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  5.55E-012  (Modified Grain method)
    Subcooled liquid VP: 4.65E-010 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):  1.284
       log Kow used: 4.55 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  29.258 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Aldehydes
       Vinyl/Allyl Ketones
       Vinyl/Allyl Ethers

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.54E-014  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  2.278E-012 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  4.55  (KowWin est)
  Log Kaw used:  -12.201  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  16.751
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :  -0.0508
   Biowin2 (Non-Linear Model)     :   0.0104
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.6688  (recalcitrant)
   Biowin4 (Primary Survey Model) :   2.9742  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.4489
   Biowin6 (MITI Non-Linear Model):   0.0309
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.7609
 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):  6.2E-008 Pa (4.65E-010 mm Hg)
  Log Koa (Koawin est  ): 16.751
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  48.4 
       Octanol/air (Koa) model:  1.38E+004 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.999 
       Mackay model           :  1 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 188.2482 E-12 cm3/molecule-sec
      Half-Life =     0.057 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.682 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    44.182999 E-17 cm3/molecule-sec
      Half-Life =     0.026 Days (at 7E11 mol/cm3)
      Half-Life =     37.350 Min
   Reaction With Nitrate Radicals May Be Important!
   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    :  381.6
      Log Koc:  2.582 

 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 = 2.802 (BCF = 634)
       log Kow used: 4.55 (estimated)

 Volatilization from Water:
    Henry LC:  1.54E-014 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 7.609E+010  hours   (3.17E+009 days)
    Half-Life from Model Lake : 8.301E+011  hours   (3.459E+010 days)

 Removal In Wastewater Treatment:
    Total removal:              58.63  percent
    Total biodegradation:        0.54  percent
    Total sludge adsorption:    58.09  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       6.22e-005       0.427        1000       
   Water     3.55            4.32e+003    1000       
   Soil      90.3            8.64e+003    1000       
   Sediment  6.1             3.89e+004    0          
     Persistence Time: 8.55e+003 hr

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