ChemSpider 2D Image | Plumbagin | C11H8O3

Plumbagin

  • Molecular FormulaC11H8O3
  • Average mass188.179 Da
  • Monoisotopic mass188.047348 Da
  • ChemSpider ID9790

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Featured data source



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

1,4-Naphthalenedione, 5-hydroxy-2-methyl- [ACD/Index Name]
1,4-Naphthalenedione, 5-hydroxy-2-methyl- (9CI)
207-569-6 [EINECS]
481-42-5 [RN]
5-Hydroxy-2-methyl-1,4-naphthochinon [German] [ACD/IUPAC Name]
5-Hydroxy-2-methyl-1,4-naphthochinone
5-Hydroxy-2-methyl-1,4-naphthoquinone [ACD/IUPAC Name]
5-Hydroxy-2-méthyl-1,4-naphtoquinone [French] [ACD/IUPAC Name]
5-hydroxy-2-methylnaphthalene-1,4-dione
L66 BV EVJ C1 GQ [WLN]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

AI3-38055 [DBID]
AIDS009323 [DBID]
AIDS-009323 [DBID]
AP-782/41885488 [DBID]
BRN 1870475 [DBID]
C10387 [DBID]
CCRIS 6671 [DBID]
CHEBI:8273 [DBID]
NCI60_001904 [DBID]
NSC 236613 [DBID]
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  • Experimental Physico-chemical Properties
  • Predicted Physico-chemical Properties
  • Miscellaneous
    • Safety:

      Corrosive/Toxic/keep cold SynQuest 2920-1-X2, 66149
      Danger Biosynth W-202844
      GHS05; GHS06 Biosynth W-202844
      H301; H314 Biosynth W-202844
      P280; P305+P351+P338; P310 Biosynth W-202844
      R25,R34,R41 SynQuest 2920-1-X2, 66149
      S13,S22,S24/25,S26,S27,S36/37/39,S45 SynQuest 2920-1-X2, 66149
    • Target Organs:

      ROS TargetMol T2841
    • Chemical Class:

      A hydroxy-1,4-naphthoquinone that is 1,4-naphthoquinone in which the hydrogens at positions 2 and 5 are substituted by methyl and hydroxy groups, respectively. ChEBI CHEBI:8273
      quinone Microsource [01505129]
    • Drug Status:

      experimental Microsource [01505129]
    • Compound Source:

      Aristea, Diospyros & Plumbago spp; Dyerophyton, Drosera, Dioncophyllum, Nepenthe, Sisyrinchium and Sparaxis tricolor Microsource [01505129]
      Constit. of various Plumbago spp., Dyerophyton africanum, Drosera congolana , many Diospyros spp., roots of Dioncophyllum thollonii, Nepenthe rafflesiana, Aristea ecklonii a Zerenex Molecular [ZBioX-0223]
    • Bio Activity:

      Anticancer agent. Induces G2/M cell cycle arrest and apoptosis in A549 cells through JNK-dependent p53 Ser15 phosphorylation; inhibits A549 and MDA-MD-231 tumour xenograft growth in nude mice. Promote s autophagic cell death in MDA-MB-231 and MCF-7 cells and inhibits Akt/mTOR signaling. Induces intracellular ROS generation in a PI 5-kinase-dependent manner. Also inhibits p300-mediated acetylation o f p53. Tocris Bioscience 4761
      Anticancer agent. Induces G2/M cell cycle arrest and apoptosis in A549 cells through JNK-dependent p53 Ser15 phosphorylation; inhibits A549 and MDA-MD-231 tumour xenograft growth in nude mice. Promotes autophagic cell death in MDA-MB-231 and MCF-7 cells and inhibits Akt/mTOR signaling. Induces intracellular ROS generation in a PI 5-kinase-dependent manner. Also inhibits p300-mediated acetylation of p53. Tocris Bioscience 4761
      Cell Biology Tocris Bioscience 4761
      Cell Cycle Tocris Bioscience 4761
      Cell Cycle Inhibitors Tocris Bioscience 4761
      Exhibits bactericidal; Zerenex Molecular [ZBioX-0223]
      Immunology/Inflammation TargetMol T2841
      Induces G2/M cell cycle arrest; anticancer Tocris Bioscience 4761
      ROS TargetMol T2841
  • Gas Chromatography
    • Retention Index (Kovats):

      1801 (estimated with error: 89) NIST Spectra mainlib_221591, replib_90114
    • Retention Index (Normal Alkane):

      1600 (Program type: Ramp; Column cl... (show more) ass: Semi-standard non-polar; Column diameter: 0.25 mm; Column length: 30 m; Column type: Capillary; Heat rate: 3 K/min; Start T: 50 C; End T: 250 C; Start time: 5 min; CAS no: 481425; Active phase: DB-5; Carrier gas: He; Phase thickness: 0.25 um; Data type: Normal alkane RI; Authors: Najafpour Navaei, M.; Mirza, M.; Dini, M., Chemical composition of the essential oil of Plumbago europaea L. roots from Iran, Flavour Fragr. J., 20, 2005, 213-214.) NIST Spectra nist ri

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

Density: 1.4±0.1 g/cm3
Boiling Point: 383.9±42.0 °C at 760 mmHg
Vapour Pressure: 0.0±0.9 mmHg at 25°C
Enthalpy of Vaporization: 65.7±3.0 kJ/mol
Flash Point: 200.2±24.4 °C
Index of Refraction: 1.631
Molar Refractivity: 49.5±0.3 cm3
#H bond acceptors: 3
#H bond donors: 1
#Freely Rotating Bonds: 0
#Rule of 5 Violations: 0
ACD/LogP: 2.45
ACD/LogD (pH 5.5): 2.25
ACD/BCF (pH 5.5): 29.64
ACD/KOC (pH 5.5): 386.89
ACD/LogD (pH 7.4): 1.49
ACD/BCF (pH 7.4): 5.22
ACD/KOC (pH 7.4): 68.19
Polar Surface Area: 54 Å2
Polarizability: 19.6±0.5 10-24cm3
Surface Tension: 57.2±3.0 dyne/cm
Molar Volume: 139.0±3.0 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) =  2.50

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  351.74  (Adapted Stein & Brown method)
    Melting Pt (deg C):  125.30  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  9.84E-006  (Modified Grain method)
    MP  (exp database):  78.5 deg C
    Subcooled liquid VP: 3.18E-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):  1385
       log Kow used: 2.50 (estimated)
       no-melting pt equation used
     Water Sol (Exper. database match) =  300 mg/L (15 deg C)
        Exper. Ref:  BEILSTEIN

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  4970.5 mg/L
    Wat Sol (Exper. database match) =  300.00
       Exper. Ref:  BEILSTEIN

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Phenols
       Quinone/Hydroquinone

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   4.04E-010  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.759E-009 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  2.50  (KowWin est)
  Log Kaw used:  -7.782  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  10.282
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.7874
   Biowin2 (Non-Linear Model)     :   0.5840
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.7947  (weeks       )
   Biowin4 (Primary Survey Model) :   3.5715  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.4833
   Biowin6 (MITI Non-Linear Model):   0.4150
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.3064
 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):  0.00424 Pa (3.18E-005 mm Hg)
  Log Koa (Koawin est  ): 10.282
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.000708 
       Octanol/air (Koa) model:  0.0047 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.0249 
       Mackay model           :  0.0536 
       Octanol/air (Koa) model:  0.273 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  23.7269 E-12 cm3/molecule-sec
      Half-Life =     0.451 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     5.410 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     1.137500 E-17 cm3/molecule-sec
      Half-Life =     1.007 Days (at 7E11 mol/cm3)
      Half-Life =     24.179 Hrs
   Reaction With Nitrate Radicals May Be Important!
   Fraction sorbed to airborne particulates (phi): 0.0392 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  43.88
      Log Koc:  1.642 

 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 = 0.389 (BCF = 2.448)
       log Kow used: 2.50 (estimated)

 Volatilization from Water:
    Henry LC:  4.04E-010 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.988E+006  hours   (8.283E+004 days)
    Half-Life from Model Lake : 2.169E+007  hours   (9.036E+005 days)

 Removal In Wastewater Treatment:
    Total removal:               3.10  percent
    Total biodegradation:        0.10  percent
    Total sludge adsorption:     2.99  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       0.00731         7.47         1000       
   Water     18.8            360          1000       
   Soil      81.1            720          1000       
   Sediment  0.131           3.24e+003    0          
     Persistence Time: 748 hr




                    

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