ChemSpider 2D Image | 5'-S-Isobutyl-5'-thioadenosine | C14H21N5O3S

5'-S-Isobutyl-5'-thioadenosine

  • Molecular FormulaC14H21N5O3S
  • Average mass339.413 Da
  • Monoisotopic mass339.136505 Da
  • ChemSpider ID110251
  • defined stereocentres - 4 of 4 defined stereocentres


More details:






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

35899-54-8 [RN]
5'-Deoxy-5'-isobutylthioadenosine
5'-S-(2-methylpropyl)-5'-thioadenosine
5'-S-Isobutyl-5'-thioadenosin [German] [ACD/IUPAC Name]
5'-S-Isobutyl-5'-thioadenosine [ACD/IUPAC Name]
5'-S-Isobutyl-5'-thioadénosine [French] [ACD/IUPAC Name]
Adenosine, 5'-S-(2-methylpropyl)-5'-thio- [ACD/Index Name]
(2R,3R,4S,5S)-2-(6-amino-9H-purin-9-yl)-5-((isobutylthio)methyl)tetrahydrofuran-3,4-diol
(2R,3R,4S,5S)-2-(6-aminopurin-9-yl)-5-(2-methylpropylsulfanylmethyl)oxolane-3,4-diol
(2R,3R,4S,5S)-2-(6-Amino-purin-9-yl)-5-isobutylsulfanylmethyl-tetrahydro-furan-3,4-diol
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  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Bio Activity:

      SIBA selectively inhibits spermine synthase, IC50=8 uM. MedChem Express
      SIBA selectively inhibits spermine synthase, IC50=8 uM.;IC50 value: 8 uM;Target: spermine synthaseSIBA is a powerful antiproliferative drug. SIBA has been reported to inhibit cell transformation induced by oncogenic RNA or DNA viruses, the growth of transformed mouse mammary cells, the mitogen-stimulated blastogenesis of lymphocytes and the capping of herpes virus mRNA 161. It has also been demonstrated that an antimalarial activity is exerted by SIBA against Plasmodium falciparum in cultures. MedChem Express HY-18684

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

Density: 1.6±0.1 g/cm3
Boiling Point: 631.2±65.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.9 mmHg at 25°C
Enthalpy of Vaporization: 98.1±3.0 kJ/mol
Flash Point: 335.5±34.3 °C
Index of Refraction: 1.753
Molar Refractivity: 85.0±0.5 cm3
#H bond acceptors: 8
#H bond donors: 4
#Freely Rotating Bonds: 5
#Rule of 5 Violations: 0
ACD/LogP: 2.08
ACD/LogD (pH 5.5): 1.05
ACD/BCF (pH 5.5): 3.68
ACD/KOC (pH 5.5): 87.60
ACD/LogD (pH 7.4): 1.07
ACD/BCF (pH 7.4): 3.81
ACD/KOC (pH 7.4): 90.73
Polar Surface Area: 145 Å2
Polarizability: 33.7±0.5 10-24cm3
Surface Tension: 67.4±7.0 dyne/cm
Molar Volume: 208.0±7.0 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) =  0.51

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  566.56  (Adapted Stein & Brown method)
    Melting Pt (deg C):  243.69  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.88E-015  (Modified Grain method)
    Subcooled liquid VP: 4.4E-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):  2648
       log Kow used: 0.51 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1e+006 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Aromatic Amines
       Imidazoles

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   7.60E-023  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  3.171E-019 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  0.51  (KowWin est)
  Log Kaw used:  -20.508  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  21.018
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.3223
   Biowin2 (Non-Linear Model)     :   0.0073
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.6254  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.4988  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.0164
   Biowin6 (MITI Non-Linear Model):   0.0023
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.2605
 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):  5.87E-011 Pa (4.4E-013 mm Hg)
  Log Koa (Koawin est  ): 21.018
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  5.11E+004 
       Octanol/air (Koa) model:  2.56E+008 
   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 = 256.5453 E-12 cm3/molecule-sec
      Half-Life =     0.042 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    30.019 Min
   Ozone Reaction:
      No Ozone Reaction Estimation
   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    :  10
      Log Koc:  1.000 

 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: 0.51 (estimated)

 Volatilization from Water:
    Henry LC:  7.6E-023 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.419E+019  hours   (5.914E+017 days)
    Half-Life from Model Lake : 1.548E+020  hours   (6.451E+018 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       3.41e-009       1            1000       
   Water     44.3            900          1000       
   Soil      55.6            1.8e+003     1000       
   Sediment  0.0878          8.1e+003     0          
     Persistence Time: 1e+003 hr




                    

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