ChemSpider 2D Image | L-AP4 | C4H10NO5P

L-AP4

  • Molecular FormulaC4H10NO5P
  • Average mass183.100 Da
  • Monoisotopic mass183.029663 Da
  • ChemSpider ID156157

  • defined stereocentres - 1 of 1 defined stereocentres

More details:

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

(2S)-2-Amino-4-phosphonobutanoic acid [ACD/IUPAC Name]
(2S)-2-Amino-4-phosphonobutansäure [German] [ACD/IUPAC Name]
(S)-2-amino-4-phosphonobutanoic acid
23052-81-5 [RN]
2-amino-4-phosphonobutyric acid
2S-amino-4-phosphono-butanoic acid
Acide (2S)-2-amino-4-phosphonobutanoïque [French] [ACD/IUPAC Name]
Butanoic acid, 2-amino-4-phosphono-, (2S)- [ACD/Index Name]
L-(+)-2-Amino-4-phosphonobutyric acid
L-2-amino-4-phosphonobutyric acid
More...

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

A7929_SIGMA [DBID]
NCGC00013365 [DBID]
NCGC00024468-01 [DBID]
NCIStruc1_000162 [DBID]
NCIStruc2_000128 [DBID]
NSC-30079 [DBID]
Tocris-0103 [DBID]
  • References
  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Chemical Class:

      A non-proteinogenc L-alpha-amino acid that is L-alpha-aminobutyric acid in which one of the hydrogens of the terminal methyl group h; as been replaced by a dihydroxy(oxido)-lambda5-phosphanyl group. I t is a potent and selective agonist for the group III metabotropic glutamate receptors (mGluR4/6/7/8). ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:143992
      A non-proteinogenc L-alpha-amino acid that is L-alpha-aminobutyric acid in which one of the hydrogens of the terminal methyl group has been replaced by a dihydroxy(oxido)-lambda(5)-phosphanyl group. I t is a potent and selective agonist for the group III metabotropic glutamate receptors (mGluR4/6/7/8). ChEBI CHEBI:143992

    • Bio Activity:

      <p>L-AP4 is a selective group III mGluR agonist (EC<sub>50</sub> values are 0.9, 252, 0.06-0.6 &mu;M at mGlu<sub>4</sub>, mGlu<sub>7</sub>, mGlu<sub>8</sub> receptors respectively and &gt;1000 &mu;M at other mGluRs) and also a weak NMDA receptor agonist.</p> <p><br />L-AP4 is a potent synaptic depressant.</p> <p><br />L-AP4 reduces glutamate release, inhibits glutamate-mediated EPSPs in the hippocampus, olfactory cortex and spinal cord&nbsp;and inhibits long term potentiation (LTP) in vivo.</p> <p><br />Additionally, L-AP4 also inhibits GABA release and reversibly reduces GABA-mediated inhibitory post-synaptic potential (IPSP) amplitude.</p> <p><br />L-AP4 also shows neuroprotective properties.</p> Hello Bio HB0370
      7-TM Receptors Tocris Bioscience 103
      Biochemicals & small molecules/Agonists & activators Hello Bio HB0370
      Glutamate (Metabotropic) Group III Receptors Tocris Bioscience 103
      Glutamate (Metabotropic) Receptors Tocris Bioscience 103
      L-AP4 is a selective group III mGluR agonist which inhibits synaptic transmission. Hello Bio HB0370
      Receptors & Transporters/G protein coupled receptors/Metabotropic glutamate/Group III (mGlu<sub>4</sub>, mGlu<sub>6</sub>, mGlu<sub>7</sub>, mGlu<sub>8</sub>) Hello Bio HB0370
      Selective group III metabotropic glutamate receptor agonist. Synaptic depressant. Agonist at the quisqualate-sensitized AP6 site in hippocampus. Also available as part of the Group III mGlu Receptor T ocriset™ and Mixed mGlu Receptor Tocriset™. DL Mixture (Cat. No. 0101) and D-isomer (Cat. No. 0102) also available. Tocris Bioscience 0103
      Selective group III metabotropic glutamate receptor agonist. Synaptic depressant. Agonist at the quisqualate-sensitized AP6 site in hippocampus. Also available as part of the Group III mGlu Receptor Tocriset? and Mixed mGlu Receptor Tocriset?. DL Mixture (Cat. No. 0101) and D-isomer (Cat. No. 0102) also available. Tocris Bioscience 103
      Selective group III metabotropic glutamate receptor agonist. Synaptic depressant. Agonist at the quisqualate-sensitized AP6 site in hippocampus. Available as part of the Group III mGlu Receptor Tocriset? and Mixed mGlu Receptor Tocriset?. DL Mixture and D-isomer also available. Tocris Bioscience 103
      Selective group III mGlu agonist Tocris Bioscience 0103, 103

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

Density: 1.6±0.1 g/cm3
Boiling Point: 491.7±55.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.7 mmHg at 25°C
Enthalpy of Vaporization: 83.1±6.0 kJ/mol
Flash Point: 251.2±31.5 °C
Index of Refraction: 1.546
Molar Refractivity: 35.6±0.3 cm3
#H bond acceptors: 6
#H bond donors: 5
#Freely Rotating Bonds: 4
#Rule of 5 Violations: 1
ACD/LogP: -2.39
ACD/LogD (pH 5.5): -6.06
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -6.19
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 131 Å2
Polarizability: 14.1±0.5 10-24cm3
Surface Tension: 88.8±3.0 dyne/cm
Molar Volume: 112.4±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) =  -4.03

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  431.18  (Adapted Stein & Brown method)
    Melting Pt (deg C):  226.38  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  5.96E-011  (Modified Grain method)
    Subcooled liquid VP: 8.61E-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):  1e+006
       log Kow used: -4.03 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1e+006 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   3.28E-019  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.436E-017 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -4.03  (KowWin est)
  Log Kaw used:  -16.873  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  12.843
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.8869
   Biowin2 (Non-Linear Model)     :   0.8968
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   3.1836  (weeks       )
   Biowin4 (Primary Survey Model) :   4.0124  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.4300
   Biowin6 (MITI Non-Linear Model):   0.2403
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  1.0863
 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):  1.15E-006 Pa (8.61E-009 mm Hg)
  Log Koa (Koawin est  ): 12.843
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  2.61 
       Octanol/air (Koa) model:  1.71 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.99 
       Mackay model           :  0.995 
       Octanol/air (Koa) model:  0.993 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  41.0056 E-12 cm3/molecule-sec
      Half-Life =     0.261 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     3.130 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.992 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  31.06
      Log Koc:  1.492 

 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: -4.03 (estimated)

 Volatilization from Water:
    Henry LC:  3.28E-019 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 2.415E+015  hours   (1.006E+014 days)
    Half-Life from Model Lake : 2.635E+016  hours   (1.098E+015 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       1.2e-009        6.26         1000       
   Water     39              360          1000       
   Soil      60.9            720          1000       
   Sediment  0.0713          3.24e+003    0          
     Persistence Time: 579 hr

Click to predict properties on the Chemicalize site


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