ChemSpider 2D Image | Nateglinide | C19H27NO3

Nateglinide

  • Molecular FormulaC19H27NO3
  • Average mass317.423 Da
  • Monoisotopic mass317.199097 Da
  • ChemSpider ID10482084
  • defined stereocentres - 3 of 3 defined stereocentres


More details:



Featured data source



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

(-)-N-(trans-4-Isopropylcyclohexanecarbonyl)-D-phenylalanine
(-)-N-(trans-4-Isopropylcyclohexyl-1-carbonyl)-D-phenylalanine
(2R)-2-({[trans-4-(1-methylethyl)cyclohexyl]carbonyl}amino)-3-phenylpropanoic acid
(2R)-2-({[trans-4-(1-Methylethyl)cyclohexyl]carbonyl}amino)-3-phenylpropansäure [German]
(2R)-2-{[(trans-4-Isopropylcyclohexyl)carbonyl]amino}-3-phenylpropanoic acid
105816-04-4 [RN]
7594
acide (2R)-2-({[trans-4-(1-méthyléthyl)cyclohexyl]carbonyl}amino)-3-phénylpropanoïque [French]
D-Phenylalanine, N-[[trans-4-(1-methylethyl)cyclohexyl]carbonyl]- [ACD/Index Name]
N-[(trans-4-Isopropylcyclohexyl)carbonyl]-D-phenylalanin [German] [ACD/IUPAC Name]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

41X3PWK4O2 [DBID]
A 4166 [DBID]
YM 026 [DBID]
A-4166 [DBID]
AY 4166 [DBID]
AY-4166 [DBID]
DJN-608 [DBID]
UN3077 [DBID]
UNII:41X3PWK4O2 [DBID]
UNII-41X3PWK4O2 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      A10BX03 Wikidata Q2254797
      GHS07 Biosynth Q-201449
      H302 Biosynth Q-201449
      P261; P280; P302+P352; P304+P340; P305+P351+P338; P312 Biosynth Q-201449
      Warning Biosynth Q-201449
    • Chemical Class:

      An <element>N</element>-acyl-<stereo>D</stereo>-phenylalanine resulting from the formal condensation of the amino group of <stereo>D</stereo>-phenylalanine with the carboxy group of <stereo>trans</ste reo>-4-isopropylcyclohexanecarboxylic acid. An orally-administered, rapidly-absorbed, short-acting insulinotropic agent, it is used for the treatment of type 2 diabetes mellitus. ChEBI CHEBI:31897
    • Drug Status:

      approved BIONET-Key Organics KS-5143
    • Bio Activity:

      Inward rectifier Potassium Channels Tocris Bioscience 4231
      Ion Channels Tocris Bioscience 4231
      Kir6 (KATP) blocker. Exhibits in vitro tissue selectivity for pancreatic ?-cell-type Kir6 channels over cardiovascular Kir6 channels; displays high affinity for SUR1/Kir6.2 channels. Hypoglycemic agen t; stimulates insulin secretion from pancreatic ?-cells by increasing cytosolic Ca2+ concentration. Tocris Bioscience 4231
      Kir6 (KATP) blocker. Exhibits in vitro tissue selectivity for pancreatic ?-cell-type Kir6 channels over cardiovascular Kir6 channels; displays high affinity for SUR1/Kir6.2 channels. Hypoglycemic agent; stimulates insulin secretion from pancreatic ?-cells by increasing cytosolic Ca2+ concentration. Tocris Bioscience 4231
      Kir6 (KATP) blocker. Exhibits in vitro tissue selectivity for pancreatic beta-cell-type Kir6 channels over cardiovascular Kir6 channels; displays high affinity for SUR1/Kir6.2 channels. Hypoglycemic agent; stimulates insulin secretion from pancreatic beta-cells by increasing cytosolic Ca2+ concentration. Tocris Bioscience 4231
      Kir6 (KATP) blocker. Exhibits in vitro tissue selectivity for pancreatic beta-cell-type Kir6 channels over cardiovascular Kir6 channels; displays high affinity for SUR1/Kir6.2 channels. Hypoglycemic agent; stimulates insulin secretion from pancreatic beta-cells by increasing cytosolic Ca2+ concentration. Also agonist at the orphan receptor MRGPRX4. Tocris Bioscience 4231
      Kir6 (KATP) blocker; displays high affinity for SUR1/Kir6.2 channels Tocris Bioscience 4231
      Nateglinide is an insulin secretagog agent used for the treatment of non-insulin-dependent diabetes mellitus (NIDDM). MedChem Express
      Nateglinide is an insulin secretagog agent used for the treatment of non-insulin-dependent diabetes mellitus (NIDDM).; Target: Others; Nateglinide is an oral antihyperglycemic agent used for the treatment of non-insulin-dependent diabetes mellitus (NIDDM). MedChem Express HY-B0422
      Oral hypoglycaemic agent; Zerenex Molecular [ZBioX-0060]
      Others MedChem Express HY-B0422
      Potassium Channels Tocris Bioscience 4231

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

Density: 1.1±0.1 g/cm3
Boiling Point: 527.6±39.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.5 mmHg at 25°C
Enthalpy of Vaporization: 84.4±3.0 kJ/mol
Flash Point: 272.9±27.1 °C
Index of Refraction: 1.536
Molar Refractivity: 89.6±0.3 cm3
#H bond acceptors: 4
#H bond donors: 2
#Freely Rotating Bonds: 6
#Rule of 5 Violations: 0
ACD/LogP: 4.21
ACD/LogD (pH 5.5): 2.00
ACD/BCF (pH 5.5): 5.66
ACD/KOC (pH 5.5): 27.95
ACD/LogD (pH 7.4): 0.63
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.19
Polar Surface Area: 66 Å2
Polarizability: 35.5±0.5 10-24cm3
Surface Tension: 44.6±3.0 dyne/cm
Molar Volume: 287.3±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) =  4.70

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  492.23  (Adapted Stein & Brown method)
    Melting Pt (deg C):  208.97  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  4.82E-010  (Modified Grain method)
    Subcooled liquid VP: 4.31E-008 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):  0.942
       log Kow used: 4.70 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  97.38 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.66E-012  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  2.137E-010 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  4.70  (KowWin est)
  Log Kaw used:  -10.168  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  14.868
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.0620
   Biowin2 (Non-Linear Model)     :   0.9854
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.7552  (weeks       )
   Biowin4 (Primary Survey Model) :   3.9171  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.0642
   Biowin6 (MITI Non-Linear Model):   0.0262
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.8178
 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):  5.75E-006 Pa (4.31E-008 mm Hg)
  Log Koa (Koawin est  ): 14.868
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.522 
       Octanol/air (Koa) model:  181 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.95 
       Mackay model           :  0.977 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  39.6705 E-12 cm3/molecule-sec
      Half-Life =     0.270 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     3.235 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.963 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  5880
      Log Koc:  3.769 

 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: 4.70 (estimated)

 Volatilization from Water:
    Henry LC:  1.66E-012 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 6.284E+008  hours   (2.618E+007 days)
    Half-Life from Model Lake : 6.855E+009  hours   (2.856E+008 days)

 Removal In Wastewater Treatment:
    Total removal:              65.98  percent
    Total biodegradation:        0.60  percent
    Total sludge adsorption:    65.39  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       0.00078         6.47         1000       
   Water     14.1            360          1000       
   Soil      77.5            720          1000       
   Sediment  8.4             3.24e+003    0          
     Persistence Time: 848 hr




                    

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