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Inherent Properties, Identifiers and References
ChemSpider ID: 9790
Empirical Formula: C11H8O3
Molecular Weight: 188.1794
Nominal Mass: 188 Da
Average Mass: 188.1794 Da
Monoisotopic Mass: 188.047344 Da
Quick Links: Permalink Similar Isomers
Systematic Name: 5-hydroxy-2-methyl-naphthalene-1,4-dione
SMILES: O=C\2c1c(O)cccc1C(=O)/C(=C/2)C
InChI: InChI=1/C11H8O3/c1-6-5-9(13)10-7(11(6)14)3-2-4-8(10)12/h2-5,12H,1​H3
InChIKey: VCMMXZQDRFWYSE-UHFFFAOYAB
(Details...) Wikipedia Article(s)
Plumbagin (5-Hydroxy-2-methyl-1,4-naphthoquinone) is a plant-derived naphthoquinone possessing a number of pharmacological activities. A yellow pigment.antimicrobial activity. In animals, it has antimalarial, anticarcinogenic, cardiotonic, antifertilityaction, and anti-atherosclerosis effects. Plumbagin is named after the plant genus Plumbago, from which it was originally isolated. Regarded as a toxin.[http://www.drugs.com/npp/black-walnut.html">It has been shown to have antimicrobial activity. In animals, it has antimalarial, anticarcinogenic, cardiotonic, antifertilityaction, and anti-atherosclerosis effects. Plumbagin is named after the plant genus Plumbago, from which it was originally isolated. Regarded as a toxin.[http://www.drugs.com/npp/black-walnut.html Read more... or Edit at Wikipedia...
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User Data

  • miscellaneous
    • Source: Aristea, Diospyros & Plumbago spp; Dyerophyton, Drosera, Dioncophyllum, Nepenthe, Sisyrinchium and Sparaxis tricolor
    • Drug Status: experimental
    • Chemical Class: quinone
Names and Synonyms

Validated by Experts, Validated by Users, Non-Validated, Removed by Users, Redirected by Users, Redirect Approved by Experts

1,4-Napht​halenedio​ne, 5-hyd​roxy-2-me​thyl- (9C​I)

207-569-6 [EINECS/ELINCS]

481-42-5 [RN]

5-hydroxy​-2-methyl​naphthale​ne-1,4-di​one

5-Hydroxy​-2-methyl​naphthoqu​inone

L66 BV EV​J C1 GQ [​WLN] [WLN]

plumbagin

1,4-Napht​halenedio​ne, 5-hyd​roxy-2-me​thyl-

2-Methylj​uglone

4-08-00-0​2376 (Bei​lstein Ha​ndbook Re​ference) [Beilstein]

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Database ID(s)

Validated by Experts, Validated by Users, Non-Validated, Removed by Users, Redirected by Users, Redirect Approved by Experts

(Details...) Predicted Properties
LogP: ACD/LogP: 2.45
XLogP: 1.20
# of Rule of 5 Violations: 0
ACD/LogD (pH 5.5): 2.42 ACD/LogD (pH 7.4): 1.67
ACD/BCF (pH 5.5): 40.04 ACD/BCF (pH 7.4): 7.06
ACD/KOC (pH 5.5): 479.8 ACD/KOC (pH 7.4): 84.56
#H bond acceptors: 3 #H bond donors: 1
#Freely Rotating Bonds: 1 Polar Surface Area: 43.37 Å2
Index of Refraction: 1.63 Molar Refractivity: 49.48 cm3
Molar Volume: 138.9 cm3 Polarizability: 19.61 10-24cm3
Surface Tension: 57.1 dyne/cm Density: 1.354 g/cm3
Flash Point: 200.2 °C Enthalpy of Vaporization: 65.73 kJ/mol
Boiling Point: 383.9 °C at 760 mmHg Vapour Pressure: 1.92E-06 mmHg at 25°C
            
 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