ChemSpider 2D Image | Icilin | C16H13N3O4

Icilin

  • Molecular FormulaC16H13N3O4
  • Average mass311.292 Da
  • Monoisotopic mass311.090607 Da
  • ChemSpider ID142218

More details:

Featured data source
The Merck Index Online

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

1-(2-Hydroxyphenyl)-4-(3-nitrophenyl)-1,2,3,6-tetra??hydro??pyrimidin-2-one
2(1H)-Pyrimidinone, 3,6-dihydro-1-(2-hydroxyphenyl)-4-(3-nitrophenyl)- [ACD/Index Name]
3-(2-hydroxyphenyl)-6-(3-nitrophenyl)-1,2,3,4-tetrahydropyrimidin-2-one
3-(2-Hydroxyphenyl)-6-(3-nitrophenyl)-3,4-dihydro-2(1H)-pyrimidinon [German] [ACD/IUPAC Name]
3-(2-Hydroxyphenyl)-6-(3-nitrophenyl)-3,4-dihydro-2(1H)-pyrimidinone [ACD/IUPAC Name]
3-(2-Hydroxyphényl)-6-(3-nitrophényl)-3,4-dihydro-2(1H)-pyrimidinone [French] [ACD/IUPAC Name]
3-(2-hydroxyphenyl)-6-(3-nitrophenyl)-3,4-dihydropyrimidin-2(1H)-one
36945-98-9 [RN]
AG-3-5
CS70PZQ4QJ
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

BRN 0700310 [DBID]
EU-0100426 [DBID]
I9532_SIGMA [DBID]
Lopac-I-9532 [DBID]
NCGC00015571-01 [DBID]
NCGC00025205-01 [DBID]
Tocris-1531 [DBID]
ZINC00620751 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Target Organs:

      TRP/TRPV Channel TargetMol T1814

    • Bio Activity:

      Activates a novel cold receptor. Cooling agent Tocris Bioscience 1531
      Biochemicals & small molecules/Agonists & activators Hello Bio HB1153
      Cooling agent that activates the novel cold receptors TRPM8 (CMR1) and TRPA1 (ANKTM1/TRPN1), members of the TRP ion channel family. Induces currents in CMR1-expressing HEK 293 cells (EC50 = 0.36 ?M) m ore potently than menthol or low temperatures. Produces "wet shakes" in vivo. Tocris Bioscience 1531
      Cooling agent that activates the novel cold receptors TRPM8 (CMR1) and TRPA1 (ANKTM1/TRPN1), members of the TRP ion channel family. Induces currents in CMR1-expressing HEK 293 cells (EC50 = 0.36 ?M) more potently than menthol or low temperatures. Produces "wet shakes" in vivo. Tocris Bioscience 1531
      Cooling agent that activates the novel cold receptors TRPM8 (CMR1) and TRPA1 (ANKTM1/TRPN1), members of the TRP ion channel family. Induces currents in CMR1-expressing HEK 293 cells (EC50 = 0.36 muM) more potently than menthol or low temperatures. Produces "wet shakes" in vivo. Tocris Bioscience 1531
      Icilin(AG 3-5) is a synthetic super-agonist of TRPM8 ion channel. MedChem Express
      Icilin(AG 3-5) is a synthetic super-agonist of TRPM8 ion channel.; IC50 value:; Target: TRPM8; in vitro: icilin, a super-cooling agent, down-regulated the expression of cell cycle signature genes and caused G1 arrest in PC-3 prostate cancer cells. MedChem Express HY-11062
      Icilin(AG 3-5) is a synthetic super-agonist of TRPM8 ion channel.;IC50 value:;Target: TRPM8;In vitro: icilin, a super-cooling agent, down-regulated the expression of cell cycle signature genes and caused G1 arrest in PC-3 prostate cancer cells. icilin affected cell cycle-related transcriptional modules and identified E2F1 transcription factor as a target master regulator of icilin. icilin reduced the activity and expression levels of E2F1 [1]. Icilin concentration-response curves were significantly shifted to the right when pH was lowered from 7.3 to 6.9, whereas those with menthol were unaltered in solutions of pH 6.1 [2]. Icilin modulated the expression level of various cell cycle regulators at transcription or post-translational levels. In addition, icilin activated JNK and p38 kinase pathways, but not ERK [4].;In vivo: Rats injected with icilin (0.5, 1, 2.5, 5mg/kg, i.p.) displayed dose-related WDS that were inhibited by pretreatment with a fixed dose of clonidine (0.15 mg/kg, MedChem Express HY-11062
      Ion Channels Tocris Bioscience 1531
      Ion channels/Voltage-gated ion channel/TRP/TRPM Hello Bio HB1153
      Membrane Tranporter/Ion Channel MedChem Express HY-11062
      Membrane Tranporter/Ion Channel; MedChem Express HY-11062
      Membrane Transporter/Ion Channel TargetMol T1814
      Potent TRPM8 channel agonist Hello Bio HB1153
      Potent TRPM8 channel agonist. Approx 200-fold more potent than methanol (EC<sub>50</sub> values of 0.36 and 66.7 &micro;M for icilin and methanol respectively). Cooling agent that also activates TRPA1 cold channel. Also TRPV3 channel inhibitor (IC<sub>50</sub> = 0.5 &micro;M). Hello Bio HB1153
      Transient Receptor Potential Channels Tocris Bioscience 1531
      TRP Channel MedChem Express HY-11062
      TRPA1 Tocris Bioscience 1531
      TRPM8 TargetMol T1814

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

Density: 1.4±0.1 g/cm3
Boiling Point: 594.8±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.7 mmHg at 25°C
Enthalpy of Vaporization: 91.9±3.0 kJ/mol
Flash Point: 313.5±30.1 °C
Index of Refraction: 1.672
Molar Refractivity: 82.4±0.3 cm3
#H bond acceptors: 7
#H bond donors: 2
#Freely Rotating Bonds: 3
#Rule of 5 Violations: 0
ACD/LogP: 2.73
ACD/LogD (pH 5.5): 2.24
ACD/BCF (pH 5.5): 29.60
ACD/KOC (pH 5.5): 393.33
ACD/LogD (pH 7.4): 2.23
ACD/BCF (pH 7.4): 29.39
ACD/KOC (pH 7.4): 390.48
Polar Surface Area: 98 Å2
Polarizability: 32.7±0.5 10-24cm3
Surface Tension: 64.8±3.0 dyne/cm
Molar Volume: 220.0±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) =  2.26

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  518.69  (Adapted Stein & Brown method)
    Melting Pt (deg C):  221.33  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  8.68E-012  (Modified Grain method)
    Subcooled liquid VP: 1.09E-009 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):  50
       log Kow used: 2.26 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  41.873 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.52E-016  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  7.111E-014 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  2.26  (KowWin est)
  Log Kaw used:  -14.207  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  16.467
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.4101
   Biowin2 (Non-Linear Model)     :   0.0469
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.3980  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.3299  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.2457
   Biowin6 (MITI Non-Linear Model):   0.0008
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.2542
 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):  1.45E-007 Pa (1.09E-009 mm Hg)
  Log Koa (Koawin est  ): 16.467
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  20.6 
       Octanol/air (Koa) model:  7.19E+003 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.999 
       Mackay model           :  0.999 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  74.7726 E-12 cm3/molecule-sec
      Half-Life =     0.143 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.717 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    13.650000 E-17 cm3/molecule-sec
      Half-Life =     0.084 Days (at 7E11 mol/cm3)
      Half-Life =      2.015 Hrs
   Reaction With Nitrate Radicals May Be Important!
   Fraction sorbed to airborne particulates (phi): 0.999 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  8397
      Log Koc:  3.924 

 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 = 1.044 (BCF = 11.06)
       log Kow used: 2.26 (estimated)

 Volatilization from Water:
    Henry LC:  1.52E-016 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 6.796E+012  hours   (2.832E+011 days)
    Half-Life from Model Lake : 7.414E+013  hours   (3.089E+012 days)

 Removal In Wastewater Treatment:
    Total removal:               2.57  percent
    Total biodegradation:        0.10  percent
    Total sludge adsorption:     2.47  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       1.59e-006       1.27         1000       
   Water     18.9            900          1000       
   Soil      81              1.8e+003     1000       
   Sediment  0.103           8.1e+003     0          
     Persistence Time: 1.55e+003 hr

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