ChemSpider 2D Image | SN-38 | C22H20N2O5

SN-38

  • Molecular FormulaC22H20N2O5
  • Average mass392.405 Da
  • Monoisotopic mass392.137207 Da
  • ChemSpider ID94634
  • defined stereocentres - 1 of 1 defined stereocentres


More details:






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

(4S)-4,11-Diethyl-4,9-dihydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]chinolin-3,14(4H,12H)-dion [German] [ACD/IUPAC Name]
(4S)-4,11-Diéthyl-4,9-dihydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoléine-3,14(4H,12H)-dione [French] [ACD/IUPAC Name]
(4S)-4,11-Diethyl-4,9-dihydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione [ACD/IUPAC Name]
1H-Pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione, 4,11-diethyl-4,9-dihydroxy-, (4S)- [ACD/Index Name]
7-Ethyl-10-hydroxycamptothecine
86639-52-3 [RN]
SN38
SN-38 [Wiki]
(+)-7-ETHYL-10-HYDROXYCAMPTOTHECIN
(19S)-10,19-diethyl-7,19-dihydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2(11),3,5,7,9,15(20)-heptaene-14,18-dione
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

AIDS058635 [DBID]
AIDS-058635 [DBID]
C11173 [DBID]
NCI60_026056 [DBID]
NSC673596 [DBID]
SN 38 [DBID]
TL8005626 [DBID]
  • Experimental Physico-chemical Properties
  • Predicted Physico-chemical Properties
  • Miscellaneous
    • Safety:

      P261; P262 Biosynth Q-100871
    • Target Organs:

      Topoisomerase inhibitor TargetMol T1703
    • Bio Activity:

      Active metabolite of CPT-11 (Cat. No. 2688) that inhibits DNA topoisomerase I (IC50 values are 0.74 and 1.9 ?M in P388 and Ehrlich cells respectively). Inhibits DNA and RNA synthesis (IC50 values are 0.077 and 1.3 ?M respectively) but does not affect protein synthesis. Displays potent antitumor activity against a range of human tumor cell lines (IC50 values are 3.3, 13, 19 and 22 nM for HCT-116, B EL-7402, HL60 and HELA cells respectively). Tocris Bioscience 2684
      Cell Cycle/DNA Damage MedChem Express HY-13704
      DNA Damage/DNA Repair TargetMol T1703
      DNA topoisomerase I TargetMol T1703
      DNA topoisomerase I inhibitor; antitumor Tocris Bioscience 2684
      SN-38(NK-012) is an active metabolite of CPT-11, inhibits DNA topoisomerase I, DNA synthesis and causes frequent DNA single-strand breaks. MedChem Express
      SN-38(NK-012) is an active metabolite of CPT-11, inhibits DNA topoisomerase I, DNA synthesis and causes frequent DNA single-strand breaks.; IC50 Value:; Target: topoisomerase I; in vitro: Among TIs, SN-38 had the highest cytotoxicity towards OSCC cell lines, with a tumor specificity index of 1321 compared to mesenchymal cells and 22 compared with epithelial cells. MedChem Express HY-13704
      Topoisomerase MedChem Express HY-13704

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

Density: 1.5±0.1 g/cm3
Boiling Point: 810.3±65.0 °C at 760 mmHg
Vapour Pressure: 0.0±3.0 mmHg at 25°C
Enthalpy of Vaporization: 123.5±3.0 kJ/mol
Flash Point: 443.8±34.3 °C
Index of Refraction: 1.738
Molar Refractivity: 104.2±0.4 cm3
#H bond acceptors: 7
#H bond donors: 2
#Freely Rotating Bonds: 2
#Rule of 5 Violations: 0
ACD/LogP: 2.31
ACD/LogD (pH 5.5): 1.81
ACD/BCF (pH 5.5): 11.76
ACD/KOC (pH 5.5): 166.48
ACD/LogD (pH 7.4): 2.09
ACD/BCF (pH 7.4): 22.54
ACD/KOC (pH 7.4): 319.09
Polar Surface Area: 100 Å2
Polarizability: 41.3±0.5 10-24cm3
Surface Tension: 83.4±5.0 dyne/cm
Molar Volume: 258.9±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) =  0.41

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  631.95  (Adapted Stein & Brown method)
    Melting Pt (deg C):  274.23  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.57E-017  (Modified Grain method)
    Subcooled liquid VP: 1.43E-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):  5808
       log Kow used: 0.41 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  327.52 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Esters
       Phenols
       Acrylamides
       Vinyl/Allyl Alcohols

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   4.25E-021  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  2.285E-021 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  0.41  (KowWin est)
  Log Kaw used:  -18.760  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  19.170
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.9316
   Biowin2 (Non-Linear Model)     :   0.9815
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.1874  (months      )
   Biowin4 (Primary Survey Model) :   3.5337  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.1363
   Biowin6 (MITI Non-Linear Model):   0.0232
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.5556
 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):  1.91E-012 Pa (1.43E-014 mm Hg)
  Log Koa (Koawin est  ): 19.170
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  1.57E+006 
       Octanol/air (Koa) model:  3.63E+006 
   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 = 188.1455 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 =    63.180000 E-17 cm3/molecule-sec
      Half-Life =     0.018 Days (at 7E11 mol/cm3)
      Half-Life =     26.120 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    :  1.313E+004
      Log Koc:  4.118 

 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: 0.41 (estimated)

 Volatilization from Water:
    Henry LC:  4.25E-021 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 2.729E+017  hours   (1.137E+016 days)
    Half-Life from Model Lake : 2.977E+018  hours   (1.24E+017 days)

 Removal In Wastewater Treatment:
    Total removal:               1.86  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.76  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       5.79e-006       0.33         1000       
   Water     47.7            1.44e+003    1000       
   Soil      52.2            2.88e+003    1000       
   Sediment  0.0951          1.3e+004     0          
     Persistence Time: 1.2e+003 hr




                    

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