ChemSpider 2D Image | Camptothecin | C20H16N2O4

Camptothecin

  • Molecular FormulaC20H16N2O4
  • Average mass348.352 Da
  • Monoisotopic mass348.110992 Da
  • ChemSpider ID22775
  • defined stereocentres - 1 of 1 defined stereocentres


More details:



Featured data source



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

(+)-Camptothecin
(+)-Camptothecine
(4S)-4-Ethyl-4-hydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]chinolin-3,14(4H,12H)-dion [German] [ACD/IUPAC Name]
(4S)-4-Éthyl-4-hydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoléine-3,14(4H,12H)-dione [French] [ACD/IUPAC Name]
(4S)-4-Ethyl-4-hydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione [ACD/IUPAC Name]
(S)-(+)-Camptothecin
(S)-4-ethyl-4-hydroxy-1H-Pyrano(3',4':6,7)indolizino(1,2-b)quinoline-3,14(4H,12H)-dione
(S)-4-ethyl-4-hydroxy-1H-Pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione
1H-Pyrano(3',4':6,7)indolizino(1,2-b)quinoline-3,14(4H,12H)-dione, 4-ethyl-4-hydroxy-, (4S)-
1H-Pyrano(3',4':6,7)indolizino(1,2-b)quinoline-3,14(4H,12H)-dione, 4-ethyl-4-hydroxy-, (S)-
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

AI3-62475 [DBID]
AIDS001995 [DBID]
AIDS-001995 [DBID]
Bio1_000400 [DBID]
Bio1_000889 [DBID]
Bio1_001378 [DBID]
BRN 0631069 [DBID]
C01897 [DBID]
C9911_SIGMA [DBID]
CCRIS 8162 [DBID]
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  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      Danger Biosynth Q-200786
      GHS06 Biosynth Q-200786
      H301; H315; H319; H335 Biosynth Q-200786
      IRRITANT Matrix Scientific 074699
      P101; P280; P301+P310; P305+P351+P338 Biosynth Q-200786
      Toxic/Keep Cold SynQuest 4H56-1-S1, 59979
    • Target Organs:

      Topoisomerase inhibitor TargetMol [T1123]
    • Chemical Class:

      A pyranoindolizinoquinoline that is pyrano[3',4':6,7]indolizino[1,2-<ital>b</ital>]quinoline which is substituted by oxo groups at positions 3 and 14, and by an ethyl group and a hydroxy group at posi tion 4 (the <stereo>S</stereo> enantiomer). ChEBI CHEBI:27656
      alkaloid Microsource [01502232]
    • Drug Status:

      experimental Microsource [01502232]
      pre-clinical BIONET-Key Organics KS-5235
    • Compound Source:

      Alkaloid from Camptotheca acuminata, Mappia foetida, Ervatamia heyneana and Ophiorrhiza mungos (Nyssaceae, Rubiaceae, Apocynaceae) Zerenex Molecular [ZBioX-0483]
      Camptotheca acuminata Microsource [01502232]
    • Bio Activity:

      ADCs cytotoxin MedChem Express HY-16560
      ADCs cytotoxin Topoisomerase MedChem Express HY-16560
      Antibody-drug conjugates/ADCs Related MedChem Express HY-16560
      Antibody-drug conjugates/ADCs Related; Cell Cycle/DNA Damage; MedChem Express HY-16560
      Camptothecin (CPT) is a potent DNA enzyme topoisomerase I (topo I) inhibitor with an IC50 and IC70 of 50 nM and 0.225 ?M for breast cancer cell line MDA-MB-231.; IC50 Value: 50 nM(in MDA-MB-231 cell line); Target: topoisomerase; Camptothecin (CPT) has recently been undergoing phase I clinical trials. MedChem Express HY-16560
      Cytotoxic plant alkaloid with antitumor properties; prototypic DNA topoisomerase I inhibitor. Induces single strand DNA breaks and protein-DNA crosslinks. Tocris Bioscience 1100
      DNA Damage/DNA Repair TargetMol [T1123]
      DNA Topoisomerase Tocris Bioscience 1100
      DNA topoisomerase inhibitor Tocris Bioscience 1100
      Enzymes Tocris Bioscience 1100
      Isomerases Tocris Bioscience 1100
      Shows potent antineoplastic activity in exp. animals; Zerenex Molecular [ZBioX-0483]
      Topoisomerase I TargetMol [T1123]

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

Density: 1.5±0.1 g/cm3
Boiling Point: 757.0±60.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.7 mmHg at 25°C
Enthalpy of Vaporization: 115.7±3.0 kJ/mol
Flash Point: 411.6±32.9 °C
Index of Refraction: 1.746
Molar Refractivity: 93.4±0.4 cm3
#H bond acceptors: 6
#H bond donors: 1
#Freely Rotating Bonds: 1
#Rule of 5 Violations: 0
ACD/LogP: 1.60
ACD/LogD (pH 5.5): 1.82
ACD/BCF (pH 5.5): 13.63
ACD/KOC (pH 5.5): 216.69
ACD/LogD (pH 7.4): 1.88
ACD/BCF (pH 7.4): 15.73
ACD/KOC (pH 7.4): 249.99
Polar Surface Area: 80 Å2
Polarizability: 37.0±0.5 10-24cm3
Surface Tension: 80.2±5.0 dyne/cm
Molar Volume: 230.2±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) =  -0.15
    Log Kow (Exper. database match) =  1.74
       Exper. Ref:  Hansch,C et al. (1995)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  573.91  (Adapted Stein & Brown method)
    Melting Pt (deg C):  247.12  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  3.76E-015  (Modified Grain method)
    Subcooled liquid VP: 9.69E-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):  207
       log Kow used: 1.74 (expkow database)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  39991 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.79E-017  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  8.326E-018 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  1.74  (exp database)
  Log Kaw used:  -14.943  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  16.683
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.7821
   Biowin2 (Non-Linear Model)     :   0.9573
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.3032  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.6261  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.2749
   Biowin6 (MITI Non-Linear Model):   0.0685
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.6258
 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):  1.29E-010 Pa (9.69E-013 mm Hg)
  Log Koa (Koawin est  ): 16.683
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  2.32E+004 
       Octanol/air (Koa) model:  1.18E+004 
   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 =  92.6270 E-12 cm3/molecule-sec
      Half-Life =     0.115 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.386 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
   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    :  2485
      Log Koc:  3.395 

 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 = 0.640 (BCF = 4.363)
       log Kow used: 1.74 (expkow database)

 Volatilization from Water:
    Henry LC:  2.79E-017 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 3.917E+013  hours   (1.632E+012 days)
    Half-Life from Model Lake : 4.273E+014  hours   (1.78E+013 days)

 Removal In Wastewater Treatment:
    Total removal:               2.07  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.97  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       0.00044         0.376        1000       
   Water     28.2            900          1000       
   Soil      71.7            1.8e+003     1000       
   Sediment  0.0841          8.1e+003     0          
     Persistence Time: 1.28e+003 hr




                    

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