ChemSpider 2D Image | Tranilast | C18H17NO5

Tranilast

  • Molecular FormulaC18H17NO5
  • Average mass327.331 Da
  • Monoisotopic mass327.110687 Da
  • ChemSpider ID4445411
  • Double-bond stereo - Double-bond stereo


More details:



Featured data source



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

2-({(2E)-3-[3,4-bis(methyloxy)phenyl]prop-2-enoyl}amino)benzoic acid
2-[[3-(3,4-dimethoxyphenyl)-1-oxoprop-2-enyl]amino]benzoic acid
2-{[(2E)-3-(3,4-Dimethoxyphenyl)-2-propenoyl]amino}benzoesäure [German] [ACD/IUPAC Name]
2-{[(2E)-3-(3,4-Dimethoxyphenyl)-2-propenoyl]amino}benzoic acid [ACD/IUPAC Name]
2-{[(2E)-3-(3,4-Dimethoxyphenyl)prop-2-enoyl]amino}benzoic acid
5070
53902-12-8 [RN]
Acide 2-{[(2E)-3-(3,4-diméthoxyphényl)-2-propenoyl]amino}benzoïque [French] [ACD/IUPAC Name]
Benzoic acid, 2-[[(2E)-3-(3,4-dimethoxyphenyl)-1-oxo-2-propen-1-yl]amino]- [ACD/Index Name]
benzoic acid, 2-[[(2E)-3-(3,4-dimethoxyphenyl)-1-oxo-2-propenyl]amino]-
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

D02027 [DBID]
EU-0101193 [DBID]
KBio3_002905 [DBID]
MK 341 [DBID]
MLS000028468 [DBID]
SB-252218 [DBID]
SMR000058373 [DBID]
SPBio_000163 [DBID]
Spectrum2_000042 [DBID]
Spectrum3_001961 [DBID]
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  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      Danger Biosynth Q-201850
      GHS05 Biosynth Q-201850
      H302 LKT Labs [T6902]
      H314 Biosynth Q-201850
      IRRITANT Matrix Scientific 076772
      None LKT Labs [T6902]
      P280; P305+P351+P338; P310 Biosynth Q-201850
      R22 LKT Labs [T6902]
      Xn LKT Labs [T6902]
    • Chemical Class:

      An amidobenzoic acid that is anthranilic acid in which one of the anilino hydrogens is replaced by a 3,4-dimethoxycinnamoyl group. ChEBI CHEBI:77572
    • Drug Status:

      USAN, INN, JAN Microsource [01505333]
    • Compound Source:

      synthetic; MK-341 Microsource [01505333]
    • Bio Activity:

      Angiotensin Receptor MedChem Express HY-18706, HY-B0195
      Antiallergic via inhibition of chemical mediator release from mast cells. Shown to be an effective inhibitor of angiogenesis. Demonstrated to antagonize the effects of angiotensin II on human arteries , possibly by an interaction at the level of the AT1 receptor. Inhibits TRPV2-mediated responses; binds to A?40 monomers and increases A?40 fibrillation. Tocris Bioscience 1098
      Antiallergic via inhibition of chemical mediator release from mast cells. Shown to be an effective inhibitor of angiogenesis. Demonstrated to antagonize the effects of angiotensin II on human arteries, possibly by an interaction at the level of the AT1 receptor. Inhibits TRPV2-mediated responses; binds to A?40 monomers and increases A?40 fibrillation. Tocris Bioscience 1098
      Antiallergic via inhibition of chemical mediator release from mast cells. Shown to be an effective inhibitor of angiogenesis. Demonstrated to antagonize the effects of angiotensin II on human arteries, possibly by an interaction at the level of the AT1 receptor. Inhibits TRPV2-mediated responses; binds to Abeta40 monomers and increases Abeta40 fibrillation. Tocris Bioscience 1098
      Antiallergic; inhibits inflammatory mediator release from mast cells Tocris Bioscience 1098
      GPCR/G protein MedChem Express HY-18706, HY-B0195
      GPCR/G protein; MedChem Express HY-18706, HY-B0195
      Miscellaneous Compounds Tocris Bioscience 1098
      Other Pharmacology Tocris Bioscience 1098
      Tranilast is an antiallergic agent. MedChem Express
      Tranilast is an antiallergic agent.; Target: Angiotensin Receptor; Tranilast has been approved in Japan and South Korea, since 1982, for the treatment of bronchial asthma, with indications for keloids and hypertrophic scar added in 1993. MedChem Express HY-B0195
      Tranilast is an antiallergic agent.;Target: Angiotensin Receptor;Tranilast has been approved in Japan and South Korea, since 1982, for the treatment of bronchial asthma, with indications for keloids and hypertrophic scar added in 1993. Tranilast is also used to treat asthma, autoimmune diseases, atopic and fibrotic pathologies, and can also inhibit angiogenesis. The antiproliferative properties of tranilast were found that tranilast elicited an inhibitory effect on fibroblast proliferation in vitro and also suppressed collagen production both in vitro and in vivo . Tranilast also reduced the release of chemical mediators from mast cells and suppressed hypersensitivity reactions. [1];Three-week-old C57Bl/10 and mdx mice received tranilast (~300 mg/kg) in their food for 9 weeks, after which fibrosis was assessed through histological analyses, and functional properties of tibialis anterior muscles were assessed in situ and diaphragm muscle strips in vitro. Tranilast administration did MedChem Express HY-B0195
      Trans-Tranilast is an antiallergic drug, used to treat bronchial asthma, allergic rhinitis and atopic dermatitis. MedChem Express
      Trans-Tranilast is an antiallergic drug, used to treat bronchial asthma, allergic rhinitis and atopic dermatitis.; Target: Angiotensin Receptor; Tranilast has been approved in Japan and South Korea, since 1982, for the treatment of bronchial asthma, with indications for keloids and hypertrophic scar added in 1993. MedChem Express HY-18706
      Trans-Tranilast is an antiallergic drug, used to treat bronchial asthma, allergic rhinitis and atopic dermatitis.;Target: Angiotensin Receptor;Tranilast has been approved in Japan and South Korea, since 1982, for the treatment of bronchial asthma, with indications for keloids and hypertrophic scar added in 1993. Tranilast is also used to treat asthma, autoimmune diseases, atopic and fibrotic pathologies, and can also inhibit angiogenesis. The antiproliferative properties of tranilast were found that tranilast elicited an inhibitory effect on fibroblast proliferation in vitro and also suppressed collagen production both in vitro and in vivo . Tranilast also reduced the release of chemical mediators from mast cells and suppressed hypersensitivity reactions. [1];Three-week-old C57Bl/10 and mdx mice received tranilast (~300 mg/kg) in their food for 9 weeks, after which fibrosis was assessed through histological analyses, and functional properties of tibialis anterior muscles were asses MedChem Express HY-18706

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

Density: 1.3±0.1 g/cm3
Boiling Point: 585.5±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.7 mmHg at 25°C
Enthalpy of Vaporization: 92.0±3.0 kJ/mol
Flash Point: 307.9±30.1 °C
Index of Refraction: 1.648
Molar Refractivity: 91.6±0.3 cm3
#H bond acceptors: 6
#H bond donors: 2
#Freely Rotating Bonds: 6
#Rule of 5 Violations: 0
ACD/LogP: 4.36
ACD/LogD (pH 5.5): 1.46
ACD/BCF (pH 5.5): 2.68
ACD/KOC (pH 5.5): 20.64
ACD/LogD (pH 7.4): 0.28
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.36
Polar Surface Area: 85 Å2
Polarizability: 36.3±0.5 10-24cm3
Surface Tension: 54.7±3.0 dyne/cm
Molar Volume: 251.9±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) =  3.62

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  535.01  (Adapted Stein & Brown method)
    Melting Pt (deg C):  228.95  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  3.63E-011  (Modified Grain method)
    MP  (exp database):  212 deg C
    Subcooled liquid VP: 3.53E-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):  6.848
       log Kow used: 3.62 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  30.404 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.03E-017  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  2.283E-012 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  3.62  (KowWin est)
  Log Kaw used:  -15.376  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  18.996
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.2425
   Biowin2 (Non-Linear Model)     :   0.9997
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.3932  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.7429  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.7031
   Biowin6 (MITI Non-Linear Model):   0.4972
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.0844
 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):  4.71E-007 Pa (3.53E-009 mm Hg)
  Log Koa (Koawin est  ): 18.996
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  6.37 
       Octanol/air (Koa) model:  2.43E+006 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.996 
       Mackay model           :  0.998 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  55.2022 E-12 cm3/molecule-sec [Cis-isomer]
      OVERALL OH Rate Constant =  57.8622 E-12 cm3/molecule-sec [Trans-isomer]
      Half-Life =    2.325 Hrs (12-hr day; 1.5E6 OH/cm3) [Cis-isomer]
      Half-Life =    2.218 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): 0.997 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  137
      Log Koc:  2.137 

 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: 3.62 (estimated)

 Volatilization from Water:
    Henry LC:  1.03E-017 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.028E+014  hours   (4.285E+012 days)
    Half-Life from Model Lake : 1.122E+015  hours   (4.675E+013 days)

 Removal In Wastewater Treatment:
    Total removal:              16.06  percent
    Total biodegradation:        0.21  percent
    Total sludge adsorption:    15.85  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       1.82e-008       3.95         1000       
   Water     11.4            900          1000       
   Soil      87.5            1.8e+003     1000       
   Sediment  1.1             8.1e+003     0          
     Persistence Time: 1.85e+003 hr




                    

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