ChemSpider 2D Image | Urocanic acid | C6H6N2O2

Urocanic acid

  • Molecular FormulaC6H6N2O2
  • Average mass138.124 Da
  • Monoisotopic mass138.042923 Da
  • ChemSpider ID1145

More details:

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

(2E)-3-(1H-Imidazol-4-yl)acrylic acid [ACD/IUPAC Name]
(2E)-3-(1H-Imidazol-4-yl)acrylsäure [German] [ACD/IUPAC Name]
104-98-3 [RN]
2-Propenoic acid, 3-(1H-imidazol-4-yl)-
2-Propenoic acid, 3-(1H-imidazol-4-yl)-, (2E)- [ACD/Index Name]
3-(1H-imidazol-4-yl)-(Z)-2-Propenoic acid
Acide (2E)-3-(1H-imidazol-4-yl)acrylique [French] [ACD/IUPAC Name]
Urocanic acid [Wiki]
(2E)-3-(1H-imidazol-4-yl)prop-2-enoic acid
(2E)-3-imidazol-4-ylprop-2-enoic acid
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

CHEBI:27248 [DBID]
MFCD00005203 [DBID]
NCI60_021801 [DBID]
NCIOpen2_003815 [DBID]
  • Miscellaneous

    • Chemical Class:

      An <locant>alpha</locant>,<locant>beta</locant>-unsaturated monocarboxylic acid that is prop-2-enoic acid substituted by a 1<element>H</element>-imidazol-4-yl group at position 3. It is a metabolite o f hidtidine. ChEBI CHEBI:27248
      An alpha,beta-unsaturated monocarboxylic acid that is prop-2-enoic acid substituted by a 1H-imidazol-4-yl group at position 3. It is a metabolite of hidtidine. ChEBI CHEBI:27248

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module, version: 14.00

Density: 1.4±0.1 g/cm3
Boiling Point: 456.9±20.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.2 mmHg at 25°C
Enthalpy of Vaporization: 75.5±3.0 kJ/mol
Flash Point: 230.1±21.8 °C
Index of Refraction: 1.674
Molar Refractivity: 36.2±0.3 cm3
#H bond acceptors: 4
#H bond donors: 2
#Freely Rotating Bonds: 2
#Rule of 5 Violations: 0
ACD/LogP: 0.01
ACD/LogD (pH 5.5): -2.55
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -3.13
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 66 Å2
Polarizability: 14.4±0.5 10-24cm3
Surface Tension: 76.7±3.0 dyne/cm
Molar Volume: 96.6±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) =  0.14

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  371.97  (Adapted Stein & Brown method)
    Melting Pt (deg C):  130.75  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.84E-007  (Modified Grain method)
    MP  (exp database):  225 deg C
    Subcooled liquid VP: 3.95E-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):  1.619e+005
       log Kow used: 0.14 (estimated)
       no-melting pt equation used
     Water Sol (Exper. database match) =  1500 mg/L (17 deg C)
        Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  92521 mg/L
    Wat Sol (Exper. database match) =  1500.00
       Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Imidazoles-acid

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   9.02E-012  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  3.188E-013 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  0.14  (KowWin est)
  Log Kaw used:  -9.433  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  9.573
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.7545
   Biowin2 (Non-Linear Model)     :   0.8443
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   3.2585  (days-weeks  )
   Biowin4 (Primary Survey Model) :   4.0340  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.5112
   Biowin6 (MITI Non-Linear Model):   0.4925
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.6849
 Ready Biodegradability Prediction:   YES

Hydrocarbon Biodegradation (BioHCwin v1.01):
    Structure incompatible with current estimation method!

 Sorption to aerosols (25 Dec C)[AEROWIN v1.00]:
  Vapor pressure (liquid/subcooled):  0.00527 Pa (3.95E-005 mm Hg)
  Log Koa (Koawin est  ): 9.573
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.00057 
       Octanol/air (Koa) model:  0.000918 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.0202 
       Mackay model           :  0.0436 
       Octanol/air (Koa) model:  0.0684 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  54.1056 E-12 cm3/molecule-sec [Cis-isomer]
      OVERALL OH Rate Constant =  56.7656 E-12 cm3/molecule-sec [Trans-isomer]
      Half-Life =    2.372 Hrs (12-hr day; 1.5E6 OH/cm3) [Cis-isomer]
      Half-Life =    2.261 Hrs (12-hr day; 1.5E6 OH/cm3) [Trans-isomer]
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     1.050000 E-17 cm3/molecule-sec [Cis-]
      OVERALL Ozone Rate Constant =     2.100000 E-17 cm3/molecule-sec [Trans-]
      Half-Life =     1.091 Days (at 7E11 mol/cm3) [Cis-isomer]
      Half-Life =    13.097 Hrs (at 7E11 mol/cm3) [Trans-isomer]
   Fraction sorbed to airborne particulates (phi): 0.0319 (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 = 0.500 (BCF = 3.162)
       log Kow used: 0.14 (estimated)

 Volatilization from Water:
    Henry LC:  9.02E-012 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 7.629E+007  hours   (3.179E+006 days)
    Half-Life from Model Lake : 8.322E+008  hours   (3.468E+007 days)

 Removal In Wastewater Treatment:
    Total removal:               1.85  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.76  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       0.000406        4.02         1000       
   Water     33.9            208          1000       
   Soil      66              416          1000       
   Sediment  0.0594          1.87e+003    0          
     Persistence Time: 389 hr

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