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Inherent Properties, Identifiers and References
ChemSpider ID: 9804
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: 4-hydroxy-3-methyl-naphthalene-1,2-dione
SMILES: O=C2/C(=C(/O)c1c(cccc1)C2=O)C
InChI: InChI=1/C11H8O3/c1-6-9(12)7-4-2-3-5-8(7)11(14)10(6)13/h2-5,12H,1H​3
InChIKey: BGVCGTNXEKDVCB-UHFFFAOYAP
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Names and Synonyms

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

1, 4-Naph​thalenedi​one, 2-hy​droxy-3-m​ethyl-

1,4-Napht​halenedio​ne, 2-hyd​roxy-3-me​thyl-

1,4-Napht​halenedio​ne, 2-hyd​roxy-3-me​thyl- (9C​I)

1,4-Napht​hoquinone​, 2-hydro​xy-3-meth​yl-

207-594-2 [EINECS/ELINCS]

2-HYDROXY​-3-METHYL​-1,4-NAPH​THALENEDI​ONE

2-Hydroxy​-3-methyl​-1,4-naph​thoquinone

2-Methyl-​3-hydroxy​-1,4-naph​thoquinone

3-Hydroxy​-2-methyl​-1, 4-nap​hthoquino​ne

3-Hydroxy​-2-methyl​-1,4-naph​thoquinone

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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: 1.83
XLogP: 1.50
# of Rule of 5 Violations: 0
ACD/LogD (pH 5.5): 0.79 ACD/LogD (pH 7.4): -0.97
ACD/BCF (pH 5.5): 1.33 ACD/BCF (pH 7.4): 1
ACD/KOC (pH 5.5): 21.59 ACD/KOC (pH 7.4): 1
#H bond acceptors: 3 #H bond donors: 1
#Freely Rotating Bonds: 1 Polar Surface Area: 43.37 Å2
Index of Refraction: 1.646 Molar Refractivity: 49.19 cm3
Molar Volume: 135.5 cm3 Polarizability: 19.5 10-24cm3
Surface Tension: 61.9 dyne/cm Density: 1.388 g/cm3
Flash Point: 181.9 °C Enthalpy of Vaporization: 63.18 kJ/mol
Boiling Point: 353.7 °C at 760 mmHg Vapour Pressure: 1.29E-05 mmHg at 25°C
(Details...) EPI Summary 
            
 Log Octanol-Water Partition Coef (SRC):
    Log Kow (KOWWIN v1.67 estimate) =  1.77

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  367.89  (Adapted Stein & Brown method)
    Melting Pt (deg C):  131.17  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.38E-007  (Modified Grain method)
    Subcooled liquid VP: 1.59E-006 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):  1539
       log Kow used: 1.77 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  134.02 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.90E-012  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  2.220E-011 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  1.77  (KowWin est)
  Log Kaw used:  -10.110  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  11.880
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.8167
   Biowin2 (Non-Linear Model)     :   0.8107
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.9433  (weeks       )
   Biowin4 (Primary Survey Model) :   3.7057  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.3467
   Biowin6 (MITI Non-Linear Model):   0.1974
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.5076
 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):  0.000212 Pa (1.59E-006 mm Hg)
  Log Koa (Koawin est  ): 11.880
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.0142 
       Octanol/air (Koa) model:  0.186 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.338 
       Mackay model           :  0.531 
       Octanol/air (Koa) model:  0.937 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  40.4471 E-12 cm3/molecule-sec
      Half-Life =     0.264 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     3.173 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    25.199999 E-17 cm3/molecule-sec
      Half-Life =     0.045 Days (at 7E11 mol/cm3)
      Half-Life =      1.091 Hrs
   Fraction sorbed to airborne particulates (phi): 0.435 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  10
      Log Koc:  1.000 

 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 = 0.664 (BCF = 4.618)
       log Kow used: 1.77 (estimated)

 Volatilization from Water:
    Henry LC:  1.9E-012 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 4.227E+008  hours   (1.761E+007 days)
    Half-Life from Model Lake : 4.611E+009  hours   (1.921E+008 days)

 Removal In Wastewater Treatment:
    Total removal:               2.08  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.99  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       6e-005          0.931        1000       
   Water     25.6            360          1000       
   Soil      74.4            720          1000       
   Sediment  0.0726          3.24e+003    0          
     Persistence Time: 683 hr
(Details...) SimBioSys LASSO
Descriptors: 0, 0, 0, 0, 0, 0, 0, 4, 0, 0, 1, 2, 3, 4, 0, 0, 10, 2, 0, 0, 0, 0, 0, 0
CategoryTargetPDB CodeLASSO Score
MetalloenzymesACE, angiotensin-converting enzyme;1o860.00
Other EnzymesAChE, acetylcholinesterase;1eve0.00
MetalloenzymesADA, adenosine deaminase;1stw0.00
Other EnzymesALR2, aldose reductase;1ah30.00
Other EnzymesAmpC, AmpC beta-lactamase;1xgj0.00
Nuclear Hormone ReceptorsAR, androgen receptor;1xq20.00
KinasesCDK2, cyclindependent kinase 2;1ckp0.00
MetalloenzymesCOMT, catechol O-methyltransferase;1h1d0.00
Other EnzymesCOX-1, cyclooxygenase-1;1p4g0.01
Other Enzymescyclooxygenase-21cx20.00
Folate EnzymesDHFR, dihydrofolate reductase;3dfr0.00
KinasesEGFr, epidermal growth factor receptor;1m170.00
Nuclear Hormone ReceptorsER, estrogen receptor; agonist1l2i0.00
Nuclear Hormone ReceptorsER, estrogen receptor; antagonist3ert0.01
KinasesFGFr1, fibroblast growth factor receptor kinase;1agw0.00
Serine ProteasesFXa, factor Xa;1f0r0.02
Folate EnzymesGART, glycinamide ribonucleotide transformylase;1c2t0.00
Other EnzymesGPB, glycogen phosphorylase â;1a8i0.00
Other EnzymesHIVPR, HIV protease;1hpx0.01
Other EnzymesHIVRT, HIV reverse transcriptase;1rt10.02
Other EnzymesHMGR, hydroxymethylglutaryl-CoA reductase;1hw80.01
KinasesHSP90, human heat shock protein 90;1uy60.01
Nuclear Hormone ReceptorsMR, mineralocorticoid receptor;2aa20.01
Other EnzymesNA, neuraminidase;1a4g0.00
KinasesP38 MAP, P38 mitogen activated protein;1kv20.00
Other EnzymesPARP, poly(ADP-ribose) polymerase;1efy0.00
KinasesPDGFrb, platelet derived growth factor receptor kinase;0.00
Other EnzymesPNP, purine nucleoside phosphorylase;1b8o0.00
Nuclear Hormone ReceptorsPPARg, peroxisome proliferator activated receptor ç;1fm90.07
Nuclear Hormone ReceptorsPR, progesterone receptor;1sr70.01
Nuclear Hormone ReceptorsRXRa, retinoic X receptor R;1mvc0.00
Other EnzymesSAHH, S-adenosyl-homocysteine hydrolase;1a7a0.00
KinasesSRC, tyrosine kinase SRC;2src0.01
Serine ProteasesThrombin1ba80.00
KinasesTK, thymidine kinase;1kim0.00
KinasesVEGFr2, vascular endothelial growth factor receptor;1vr20.02