ChemSpider 2D Image | S-(−)-Willardiine | C7H9N3O4

S-(−)-Willardiine

  • Molecular FormulaC7H9N3O4
  • Average mass199.164 Da
  • Monoisotopic mass199.059311 Da
  • ChemSpider ID389063

  • defined stereocentres - 1 of 1 defined stereocentres

More details:

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

S-(−)-Willardiine
(S)-Willardiine
21416-43-3 [RN]
3-(2,4-Dioxo-3,4-dihydro-1(2H)-pyrimidinyl)-L-alanin [German] [ACD/IUPAC Name]
3-(2,4-Dioxo-3,4-dihydro-1(2H)-pyrimidinyl)-L-alanine [ACD/IUPAC Name]
3-(2,4-Dioxo-3,4-dihydro-1(2H)-pyrimidinyl)-L-alanine [French] [ACD/IUPAC Name]
3-(2,4-Dioxo-3,4-dihydropyrimidin-1(2H)-yl)-L-alanine
3-(uracil-1-yl)-L-alanine
3-(uracil-1-yl)-L-alanine zwitterion
L-Alanine, 3-(3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl)- [ACD/Index Name]
More...

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

C03584 [DBID]
CHEBI:15851 [DBID]
EU-0101219 [DBID]
W105_SIGMA [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Chemical Class:

      Glutamate EU-OpenScreen [W-105]
      The 3-(uracil-1-yl) derivative of <stereo>L</stereo>-alanine. ChEBI CHEBI:15851, CHEBI:57543
      The 3-(uracil-1-yl) derivative of L-alanine. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:15851, CHEBI:15851
      Zwitterionic form of 3-(uracil-1-yl)-<stereo>L</stereo>-alanine having an anionic carboxy group and a protonated amino group. ChEBI CHEBI:15851, CHEBI:57543
      Zwitterionic form of 3-(uracil-1-yl)-L-alanine having an anionic carboxy group and a protonated amino group. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:57543, CHEBI:57543

    • Compound Source:

      Linum usitatissimum PlantCyc 3-URACIL-1-YL-L-SERINE
      willardiine and isowillardiine biosynthesis PlantCyc 3-URACIL-1-YL-L-SERINE

    • Bio Activity:

      (S)-Willardiine is a potent agonist of AMPA/kainate receptors with EC50 of 44.8 uM. MedChem Express
      (S)-Willardiine is a potent agonist of AMPA/kainate receptors with EC50 of 44.8 uM.; IC50 value: 44.8 uM(EC50) [1]; Target: AMPA/kainate receptor agonist; in vitro: The (S)- but not (R)-isomers of willardiine and 5-bromowillardiine were potent agonists, producing rapidly but incompletely desensitizing responses [1]. MedChem Express HY-12499
      (S)-Willardiine is a potent agonist of AMPA/kainate receptors with EC50 of 44.8 uM.;IC50 value: 44.8 uM(EC50) [1];Target: AMPA/kainate receptor agonist;In vitro: The (S)- but not (R)-isomers of willardiine and 5-bromowillardiine were potent agonists, producing rapidly but incompletely desensitizing responses [1]. At a concentration of 1.8 mM, Ca2+ inhibited the currents induced by 100 microM willardiine by approximately 50% [2].;In vivo: In newborn mice (P5, histopathology at P10), local injection of the AMPA receptor agonist S-bromo-willardiine at day 5 after birth induced cortical damage and white matter damage, which was reduced in a dose-dependent manner by the AMPA receptor antagonists [3]. MedChem Express HY-12499
      AMPAR MedChem Express HY-12499
      Membrane Tranporter/Ion Channel MedChem Express HY-12499
      Membrane Tranporter/Ion Channel; Neuronal Signaling; MedChem Express HY-12499
      uracil + O-acetyl-L-serine -> L-willardiine + acetate + H+ PlantCyc 3-URACIL-1-YL-L-SERINE

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

Density: 1.5±0.1 g/cm3
Boiling Point:
Vapour Pressure:
Enthalpy of Vaporization:
Flash Point:
Index of Refraction: 1.582
Molar Refractivity: 44.2±0.3 cm3
#H bond acceptors: 7
#H bond donors: 4
#Freely Rotating Bonds: 3
#Rule of 5 Violations: 0
ACD/LogP: -1.47
ACD/LogD (pH 5.5): -4.22
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -4.24
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 113 Å2
Polarizability: 17.5±0.5 10-24cm3
Surface Tension: 69.7±3.0 dyne/cm
Molar Volume: 132.6±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) =  -4.48

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  529.07  (Adapted Stein & Brown method)
    Melting Pt (deg C):  311.20  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  3.08E-012  (Modified Grain method)
    Subcooled liquid VP: 5.01E-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):  1.231e+005
       log Kow used: -4.48 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  37982 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Aliphatic Amines-acid
       Imides-acid

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   3.86E-018  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  6.557E-018 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -4.48  (KowWin est)
  Log Kaw used:  -15.802  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  11.322
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.8792
   Biowin2 (Non-Linear Model)     :   0.8736
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   3.1481  (weeks       )
   Biowin4 (Primary Survey Model) :   3.9892  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.3452
   Biowin6 (MITI Non-Linear Model):   0.1205
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.9132
 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):  6.68E-007 Pa (5.01E-009 mm Hg)
  Log Koa (Koawin est  ): 11.322
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  4.49 
       Octanol/air (Koa) model:  0.0515 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.994 
       Mackay model           :  0.997 
       Octanol/air (Koa) model:  0.805 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  51.6419 E-12 cm3/molecule-sec
      Half-Life =     0.207 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     2.485 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     0.175000 E-17 cm3/molecule-sec
      Half-Life =     6.549 Days (at 7E11 mol/cm3)
   Fraction sorbed to airborne particulates (phi): 0.996 (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: -4.48 (estimated)

 Volatilization from Water:
    Henry LC:  3.86E-018 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 2.141E+014  hours   (8.919E+012 days)
    Half-Life from Model Lake : 2.335E+015  hours   (9.73E+013 days)

 Removal In Wastewater Treatment:
    Total removal:               1.85  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.75  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       3.94e-008       4.82         1000       
   Water     39              360          1000       
   Soil      60.9            720          1000       
   Sediment  0.0713          3.24e+003    0          
     Persistence Time: 579 hr

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