ChemSpider 2D Image | L-(-)-Phenylalanine | C9H11NO2


  • Molecular FormulaC9H11NO2
  • Average mass165.189 Da
  • Monoisotopic mass165.078979 Da
  • ChemSpider ID5910
  • defined stereocentres - 1 of 1 defined stereocentres

More details:

Featured data source

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

(2S)-2-amino-3-phenylpropanoic acid
(L)-Phenylalanine [RN]
(S)-2-Amino-3-phenylpropanoic acid
(S)-2-Amino-3-phenylpropionic acid
(S)-A-Aminobenzenepropanoic Acid
(S)-a-Amino-b-phenylpropionic Acid
(S)-a-Aminohydrocinnamic Acid

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

47E5O17Y3R [DBID]
6168 [DBID]
AY7535000 [DBID]
78019_FLUKA [DBID]
78030_FLUKA [DBID]
Antibiotic FN 1636 [DBID]
bmse000045 [DBID]
BR-25441 [DBID]
BR-46761 [DBID]
C00079 [DBID]
  • References
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Appearance:

      Colourless or white platelike crystals or crystalline powder; odourless Food and Agriculture Organization of the United Nations L-Phenylalanine
      white crystalline powder OU Chemical Safety Data (No longer updated) More details
    • Stability:

      Stable. Incompatible with strong oxidizing agents. OU Chemical Safety Data (No longer updated) More details
    • Toxicity:

      IPR-RAT LD50 5287 mg kg-1 OU Chemical Safety Data (No longer updated) More details
    • Safety:

      Safety glasses. OU Chemical Safety Data (No longer updated) More details
      WARNING: Not for human consumption, may irriate skin & eyes. Alfa Aesar A13238
      WARNING: Not sold for human treatment, trials or use Alfa Aesar A13238
    • Chemical Class:

      An amino acid zwitterion arising from transfer of a proton from the carboxy to the amino group of <stereo>L</stereo>-phenylalanine; major species at pH 7.3. ChEBI CHEBI:17295, CHEBI:58095
      An amino acid zwitterion arising from transfer of a proton from the carboxy to the amino group of L-phenylalanine; major species at pH 7.3. ChEBI, CHEBI:58095
      The <stereo>L</stereo>-enantiomer of phenylalanine. ChEBI CHEBI:17295, CHEBI:58095
      The L-enantiomer of phenylalanine. ChEBI, CHEBI:17295
    • Compound Source:

      3-amino-3-phenylpropanoyl-CoA biosynthesis PlantCyc PHE
      Aegilops tauschii PlantCyc PHE
      Amaranthus hypochondriacus PlantCyc PHE
      Amborella trichopoda PlantCyc PHE
      Anacardium occidentale PlantCyc PHE
      Ananas comosus PlantCyc PHE
      Aquilegia coerulea PlantCyc PHE
      Arabidopsis halleri PlantCyc PHE
      Arabidopsis lyrata PlantCyc PHE
      Arabidopsis thaliana col PlantCyc PHE
      Asparagus officinalis PlantCyc PHE
      benzoate biosynthesis II (CoA-independent, non-beta-oxidative) PlantCyc PHE
      Beta vulgaris subsp. vulgaris PlantCyc PHE
      Boechera stricta PlantCyc PHE
      Brachypodium distachyon PlantCyc PHE
      Brassica napus PlantCyc PHE
      Brassica oleracea var. capitata PlantCyc PHE
      Brassica oleracea var. oleracea PlantCyc PHE
      Brassica rapa FPsc PlantCyc PHE
      Brassica rapa subsp. pekinensis PlantCyc PHE
      Calotropis gigantea PlantCyc PHE
      Camptotheca acuminata PlantCyc PHE
      Cannabis sativa PlantCyc PHE
      Capsella grandiflora PlantCyc PHE
      Capsella rubella PlantCyc PHE
      Capsicum annuum PlantCyc PHE
      Carica papaya PlantCyc PHE
      Catharanthus roseus PlantCyc PHE
      Chenopodium quinoa PlantCyc PHE
      Chlamydomonas reinhardtii PlantCyc PHE
      Chromochloris zofingiensis PlantCyc PHE
      Cicer arietinum PlantCyc PHE
      Citrus clementina PlantCyc PHE
      Citrus sinensis PlantCyc PHE
      Coccomyxa subellipsoidea C-169 PlantCyc PHE
      Corchorus capsularis PlantCyc PHE
      Cucumis sativus PlantCyc PHE
      Daucus carota subsp. sativus PlantCyc PHE
      Dianthus caryophyllus PlantCyc PHE
      Dioscorea rotundata PlantCyc PHE
      ephedrine biosynthesis PlantCyc PHE
      Eucalyptus grandis PlantCyc PHE
      Eutrema salsugineum PlantCyc PHE
      Fragaria vesca subsp. vesca PlantCyc PHE
      glucosinolate biosynthesis from phenylalanine PlantCyc PHE
      Glycine max PlantCyc PHE
      Gossypium raimondii PlantCyc PHE
      Helianthus annuus PlantCyc PHE
      Hordeum vulgare subsp. vulgare PlantCyc PHE
      Humulus lupulus var. lupulus PlantCyc PHE
      indole-3-acetate inactivation V PlantCyc PHE
      indole-3-acetate inactivation VIII PlantCyc PHE
      jasmonoyl-amino acid conjugates biosynthesis I PlantCyc PHE
      Kalanchoe fedtschenkoi PlantCyc PHE
      Kalanchoe laxiflora PlantCyc PHE
      Leersia perrieri PlantCyc PHE
      Linum usitatissimum PlantCyc PHE
      Lotus japonicus PlantCyc PHE
      L-phenylalanine -> (3R)-beta-phenylalanine PlantCyc PHE
      L-phenylalanine + 2 a reduced [NADPH-hemoprotein reductase] + 2 oxygen -> (E)-phenylacetaldehyde oxime + 2 an oxidized [NADPH-hemoprotein reductase] + CO2 + 3 H2O PlantCyc PHE
      L-phenylalanine biosynthesis II PlantCyc PHE
      L-phenylalanine biosynthesis III (cytosolic, plants) PlantCyc PHE
      L-phenylalanine degradation III PlantCyc PHE
      L-phenylalanine degradation V PlantCyc PHE
      Malus domestica PlantCyc PHE
      Manihot esculenta PlantCyc PHE
      Marchantia polymorpha PlantCyc PHE
      Medicago truncatula PlantCyc PHE
      Micromonas commoda RCC299 PlantCyc PHE
      Micromonas pusilla CCMP1545 PlantCyc PHE
      Mimulus guttatus PlantCyc PHE
      Miscanthus sinensis PlantCyc PHE
      Musa acuminata PlantCyc PHE
      Nicotiana tabacum PlantCyc PHE
      Olea europaea var. sylvestris PlantCyc PHE
      Oropetium thomaeum PlantCyc PHE
      Oryza brachyantha PlantCyc PHE
      Oryza glaberrima PlantCyc PHE
      Oryza punctata PlantCyc PHE
      Oryza rufipogon PlantCyc PHE
      Oryza sativa Japonica Group PlantCyc PHE
      Ostreococcus lucimarinus PlantCyc PHE
      Panicum hallii PlantCyc PHE
      Panicum virgatum PlantCyc PHE
      Petunia axillaris PlantCyc PHE
      Phaseolus vulgaris PlantCyc PHE
      phenylethanol biosynthesis PlantCyc PHE
      phenylpropanoid biosynthesis, initial reactions PlantCyc PHE
      Physcomitrella patens PlantCyc PHE
      Populus trichocarpa PlantCyc PHE
      prunasin and amygdalin biosynthesis PlantCyc PHE
      Prunus persica PlantCyc PHE
      Ricinus communis PlantCyc PHE
      Rosa chinensis PlantCyc PHE
      Rosa multiflora PlantCyc PHE
      Salvia miltiorrhiza PlantCyc PHE
      Selaginella moellendorffii PlantCyc PHE
      Setaria italica PlantCyc PHE
      Setaria viridis PlantCyc PHE
      Solanum lycopersicum PlantCyc PHE
      Solanum melongena PlantCyc PHE
      Solanum pennellii PlantCyc PHE
      Solanum tuberosum PlantCyc PHE
      Sorghum bicolor PlantCyc PHE
      Sphagnum fallax PlantCyc PHE
      Spinacia oleracea PlantCyc PHE
      Spirodela polyrhiza PlantCyc PHE
      suberin monomers biosynthesis PlantCyc PHE
      Thellungiella parvula PlantCyc PHE
      Theobroma cacao PlantCyc PHE
      trans-cinnamoyl-CoA biosynthesis PlantCyc PHE
      Trifolium pratense PlantCyc PHE
      Triticum aestivum PlantCyc PHE
      Triticum urartu PlantCyc PHE
      Vitis vinifera PlantCyc PHE
      Volvox carteri PlantCyc PHE
      Zea mays subsp. mays PlantCyc PHE
      Zostera marina PlantCyc PHE
    • Bio Activity:

      (indol-3-yl)acetate + L-phenylalanine + ATP -> indole-3-acetyl-L-phenylalanine + AMP + diphosphate + H+ PlantCyc PHE
      a jasmonate + L-phenylalanine + ATP -> a jasmonoyl-L-phenylalanine + AMP + diphosphate + H+ PlantCyc PHE
      an N10-formyl-tetrahydrofolate + L-phenylalanine + L-phenylalanine + an N10-formyl-tetrahydrofolate + oxygen + oxygen -> L-tyrosine + a 10-formyltetrahydrofolate-4a-carbinolamine + a 10-formyltetrahydrofolate-4a-carbinolamine + L-tyrosine PlantCyc PHE
      Calcium Channel MedChem Express HY-N0215
      keto-phenylpyruvate + L-glutamate <--> L-phenylalanine + 2-oxoglutarate PlantCyc PHE
      keto-phenylpyruvate + L-tyrosine <--> L-phenylalanine + 4-hydroxyphenylpyruvate PlantCyc PHE
      L-arogenate + H+ -> CO2 + L-phenylalanine + H2O PlantCyc PHE
      L-phenylalanine -> (3R)-beta-phenylalanine PlantCyc PHE
      L-phenylalanine -> trans-cinnamate + ammonium PlantCyc PHE
      L-phenylalanine + a reduced [NADPH-hemoprotein reductase] + oxygen -> N-hydroxy-L-phenylalanine + an oxidized [NADPH-hemoprotein reductase] + H2O + H+ PlantCyc PHE
      L-phenylalanine + an N10-formyl-tetrahydrofolate + oxygen -> a 10-formyltetrahydrofolate-4a-carbinolamine + L-tyrosine PlantCyc PHE
      L-phenylalanine + H+ -> 2-phenylethylamine + CO2 PlantCyc PHE
      L-phenylalanine + H+ + oxygen + H2O -> phenylacetaldehyde + ammonium + hydrogen peroxide + CO2 PlantCyc PHE
      L-Phenylalanine is an antagonist at ?2? calcium channels with a Ki of 980 nM. MedChem Express HY-N0215
      L-tyrosine + keto-phenylpyruvate + keto-phenylpyruvate + L-tyrosine <--> 4-hydroxyphenylpyruvate + L-phenylalanine + L-phenylalanine + 4-hydroxyphenylpyruvate PlantCyc PHE
      Membrane Tranporter/Ion Channel MedChem Express HY-N0215
      Membrane Tranporter/Ion Channel; MedChem Express HY-N0215
      pyruvate + L-phenylalanine <--> keto-phenylpyruvate + L-alanine PlantCyc PHE

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

Density: 1.2±0.1 g/cm3
Boiling Point: 307.5±30.0 °C at 760 mmHg
Vapour Pressure: 0.0±0.7 mmHg at 25°C
Enthalpy of Vaporization: 57.9±3.0 kJ/mol
Flash Point: 139.8±24.6 °C
Index of Refraction: 1.576
Molar Refractivity: 45.5±0.3 cm3
#H bond acceptors: 3
#H bond donors: 3
#Freely Rotating Bonds: 3
#Rule of 5 Violations: 0
ACD/LogP: 1.11
ACD/LogD (pH 5.5): -1.45
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -1.46
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 63 Å2
Polarizability: 18.0±0.5 10-24cm3
Surface Tension: 53.6±3.0 dyne/cm
Molar Volume: 137.4±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) =  -1.28
    Log Kow (Exper. database match) =  -1.38
       Exper. Ref:  Avdeef,A (1997)
    Log Kow (Exper. database match) =  -1.44
       Exper. Ref:  Hansch,C et al. (1995)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  392.57  (Adapted Stein & Brown method)
    Melting Pt (deg C):  248.87  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.62E-007  (Modified Grain method)
    MP  (exp database):  186 dec deg C
    Subcooled liquid VP: 1.26E-005 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):  9357
       log Kow used: -1.44 (expkow database)
       no-melting pt equation used
     Water Sol (Exper. database match) =  2.69e+004 mg/L (25 deg C)
        Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)
     Water Sol (Exper. database match) =  1.42e+004 mg/L (25 deg C)
        Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)
     Water Sol (Exper. database match) =  2.82e+004 mg/L (16 deg C)
        Exper. Ref:  MERCK INDEX (1996)

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  3026.8 mg/L
    Wat Sol (Exper. database match) =  26900.00
       Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)
    Wat Sol (Exper. database match) =  14200.00
       Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)
    Wat Sol (Exper. database match) =  28200.00
       Exper. Ref:  MERCK INDEX (1996)

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.20E-010  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  6.086E-012 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -1.44  (exp database)
  Log Kaw used:  -8.309  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  6.869
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.0782
   Biowin2 (Non-Linear Model)     :   0.9918
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   3.1703  (weeks       )
   Biowin4 (Primary Survey Model) :   3.9746  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.3699
   Biowin6 (MITI Non-Linear Model):   0.2656
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.6535
 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):  0.00168 Pa (1.26E-005 mm Hg)
  Log Koa (Koawin est  ): 6.869
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.00179 
       Octanol/air (Koa) model:  1.82E-006 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.0606 
       Mackay model           :  0.125 
       Octanol/air (Koa) model:  0.000145 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  44.1576 E-12 cm3/molecule-sec
      Half-Life =     0.242 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     2.907 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.0928 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  59.98
      Log Koc:  1.778 

 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: -1.44 (expkow database)

 Volatilization from Water:
    Henry LC:  1.2E-010 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 6.271E+006  hours   (2.613E+005 days)
    Half-Life from Model Lake : 6.841E+007  hours   (2.85E+006 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       0.00288         5.81         1000       
   Water     39              360          1000       
   Soil      60.9            720          1000       
   Sediment  0.0714          3.24e+003    0          
     Persistence Time: 578 hr


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