ChemSpider 2D Image | LAPACHONE | C15H14O3

LAPACHONE

  • Molecular FormulaC15H14O3
  • Average mass242.270 Da
  • Monoisotopic mass242.094299 Da
  • ChemSpider ID3748

More details:






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

2,2-Dimethyl-3,4-dihydro-2H-benzo[h]chromen-5,6-dion [German] [ACD/IUPAC Name]
2,2-Dimethyl-3,4-dihydro-2H-benzo[h]chromene-5,6-dione [ACD/IUPAC Name]
2,2-Diméthyl-3,4-dihydro-2H-benzo[h]chromène-5,6-dione [French] [ACD/IUPAC Name]
2H-Naphtho[1,2-b]pyran-5,6-dione, 3,4-dihydro-2,2-dimethyl- [ACD/Index Name]
3,4-Dihydro-2,2-dimethyl-2H-naphtho[2,3-b]pyran-5,10-dione
4707-32-8 [RN]
6N4FA2QQ6A
LAPACHONE
MFCD01712233
QL6127400
More...

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

ARQ 501 [DBID]
C014638 [DBID]
L2037_SIGMA [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Chemical Class:

      A benzochromenone that is 3,4-dihydro-2<element>H</element>-benzo[<ital>h</ital>]chromene-5,6-dione substituted by geminal methyl groups at position 2. Isolated from <ital>Tabebuia avellanedae</ital>, it exhibits antineoplastic and anti-inflammatory activities. ChEBI CHEBI:10429
      A benzochromenone that is 3,4-dihydro-2H-benzo[h]chromene-5,6-dione substituted by geminal methyl groups at position 2. Isolated from Tabebuia avellanedae,; it exhibits antineoplastic and anti-inflam matory activities. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:10429
      Apoptosis EU-OpenScreen [L 2037]
    • Bio Activity:

      ?-Lapachone(ARQ-501; beta-lapachone) is a naturally occurring quinone obtained from the bark of the lapacho tree (Tabebuia avellanedae) with cancer chemopreventive properties; potent inhibitor of IDO1(IC50=0.44 uM).; IC50 value: 0.44 uM (IDO1); Target: IDO1 inhibitor; anticancer agent; in vitro: ?-Lapachone markedly induced cell death without caspase activation. MedChem Express HY-13555
      Cell Cycle/DNA Damage MedChem Express HY-13555
      Cell Cycle/DNA Damage; Metabolic Enzyme/Protease; MedChem Express HY-13555
      DNA Topoisomerase Tocris Bioscience 1293
      DNA topoisomerase I inhibitor Tocris Bioscience 1293
      DNA topoisomerase I inhibitor. Exhibits a different inhibitory mechanism to camptothecin (Cat. No. 1100). Induces apoptosis in a variety of cell lines, including prostate cancer and promyelocytic leuk emia cells; blocks the cell cycle in G0/G1. Also has effects on DNA topoisomerase II, NF-?B, AP-1, and JNK. Tocris Bioscience 1293
      DNA topoisomerase I inhibitor. Exhibits a different inhibitory mechanism to camptothecin (Cat. No. 1100). Induces apoptosis in a variety of cell lines, including prostate cancer and promyelocytic leukemia cells; blocks the cell cycle in G0/G1. Also has effects on DNA topoisomerase II, NF-?B, AP-1, and JNK. Tocris Bioscience 1293
      DNA topoisomerase I inhibitor. Exhibits a different inhibitory mechanism to camptothecin (Cat. No. 1100). Induces apoptosis in a variety of cell lines, including prostate cancer and promyelocytic leukemia cells; blocks the cell cycle in G0/G1. Also has effects on DNA topoisomerase II, NF-kappaB, AP-1, and JNK. Tocris Bioscience 1293
      Enzymes Tocris Bioscience 1293
      Isomerases Tocris Bioscience 1293
      Topoisomerase MedChem Express HY-13555
  • Gas Chromatography

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

Density: 1.3±0.1 g/cm3
Boiling Point: 381.4±42.0 °C at 760 mmHg
Vapour Pressure: 0.0±0.9 mmHg at 25°C
Enthalpy of Vaporization: 63.0±3.0 kJ/mol
Flash Point: 169.7±27.9 °C
Index of Refraction: 1.595
Molar Refractivity: 65.8±0.4 cm3
#H bond acceptors: 3
#H bond donors: 0
#Freely Rotating Bonds: 0
#Rule of 5 Violations: 0
ACD/LogP: 2.82
ACD/LogD (pH 5.5): 2.77
ACD/BCF (pH 5.5): 75.01
ACD/KOC (pH 5.5): 765.28
ACD/LogD (pH 7.4): 2.77
ACD/BCF (pH 7.4): 75.01
ACD/KOC (pH 7.4): 765.28
Polar Surface Area: 43 Å2
Polarizability: 26.1±0.5 10-24cm3
Surface Tension: 48.4±5.0 dyne/cm
Molar Volume: 193.5±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) =  3.20

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  373.97  (Adapted Stein & Brown method)
    Melting Pt (deg C):  137.84  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.58E-006  (Modified Grain method)
    Subcooled liquid VP: 3.54E-005 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):  48.47
       log Kow used: 3.20 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  89.373 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   6.29E-010  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.697E-008 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  3.20  (KowWin est)
  Log Kaw used:  -7.590  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  10.790
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.1009
   Biowin2 (Non-Linear Model)     :   0.0037
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.4430  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.3350  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.1336
   Biowin6 (MITI Non-Linear Model):   0.0398
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.5363
 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):  0.00472 Pa (3.54E-005 mm Hg)
  Log Koa (Koawin est  ): 10.790
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.000636 
       Octanol/air (Koa) model:  0.0151 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.0224 
       Mackay model           :  0.0484 
       Octanol/air (Koa) model:  0.548 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  57.8428 E-12 cm3/molecule-sec
      Half-Life =     0.185 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     2.219 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    68.249992 E-17 cm3/molecule-sec
      Half-Life =     0.017 Days (at 7E11 mol/cm3)
      Half-Life =     24.179 Min
   Fraction sorbed to airborne particulates (phi): 0.0354 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  29.92
      Log Koc:  1.476 

 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 = 1.762 (BCF = 57.87)
       log Kow used: 3.20 (estimated)

 Volatilization from Water:
    Henry LC:  6.29E-010 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.449E+006  hours   (6.037E+004 days)
    Half-Life from Model Lake : 1.581E+007  hours   (6.586E+005 days)

 Removal In Wastewater Treatment:
    Total removal:               7.80  percent
    Total biodegradation:        0.14  percent
    Total sludge adsorption:     7.66  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       0.00379         0.369        1000       
   Water     13.7            900          1000       
   Soil      85.8            1.8e+003     1000       
   Sediment  0.491           8.1e+003     0          
     Persistence Time: 1.55e+003 hr




                    

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