ChemSpider 2D Image | L-Tryptophan | C11H12N2O2

L-Tryptophan

  • Molecular FormulaC11H12N2O2
  • Average mass204.225 Da
  • Monoisotopic mass204.089874 Da
  • ChemSpider ID6066
  • defined stereocentres - 1 of 1 defined stereocentres


More details:



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

L-Tryptophan [ACD/Index Name] [ACD/IUPAC Name] [JP15]
(−)-tryptophan
(-)-Tryptophan
(2S)-2-Amino-3-(1H-indol-3-yl)propansäure [German]
(L)-TRYPTOPHAN
(S)-1H-Indole-3-alanine
(S)-2-Amino-3-(3-indolyl)propionic acid
(S)-a-Amino-1H-indole-3-propanoic acid
(S)-a-Aminoindole-3-propionic acid
(S)-tryptophan
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

6173 [DBID]
8DUH1N11BX [DBID]
MFCD00064340 [DBID]
YN6130000 [DBID]
78019_FLUKA [DBID]
93659_FLUKA [DBID]
93670_FLUKA [DBID]
AI3-18478 [DBID]
AIDS011920 [DBID]
AIDS-011920 [DBID]
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  • Experimental Physico-chemical Properties
  • Predicted Physico-chemical Properties
  • Miscellaneous
    • Appearance:

      yellowish-white crystals or powder OU Chemical Safety Data (No longer updated) More details
    • Stability:

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 OU Chemical Safety Data (No longer updated) More details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

      IPR-RAT LD50 1634 mg kg-1, IPR-MUS LD50 4800 mg kg-1, ORL-RAT LD50 > 16000 mg kg-1 OU Chemical Safety Data (No longer updated) More details
      Organic Compound; Amine; Drug; Food Toxin; Dietary Supplement; Micronutrient; Metabolite; Nutraceutical; Animal Toxin; Natural Compound; Supplement; Antidepressive Agent, Second-Generation; Amino Acid, Essential Toxin, Toxin-Target Database T3D4369
    • Safety:

      Irrritant SynQuest 4H57-1-56
      Minimize exposure. OU Chemical Safety Data (No longer updated) More details
      N06AX02 Wikidata Q181003
      WARNING: Not for human consumption, may irriate skin & eyes. Alfa Aesar A10230
      WARNING: Not sold for human treatment, trials or use Alfa Aesar A10230
    • Chemical Class:

      An <stereo>L</stereo>-<locant>alpha</locant>-amino acid zwitterion obtained by transfer of a proton from the carboxy to the amino group of <stereo>L</stereo>-tryptophan; major species at pH 7.3. ChEBI CHEBI:16828, CHEBI:32712, CHEBI:57912
      An L-alpha-amino acid zwitterion obtained by transfer of a proton from the carboxy to the amino group of L-tryptophan; major species at pH 7.3. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:57912
      The <stereo>L</stereo>-enantiomer of tryptophan. ChEBI CHEBI:16828, CHEBI:32712, CHEBI:57912
      The <stereo>L</stereo>-enantiomer of tryptophanyl radical. ChEBI CHEBI:16828, CHEBI:32712, CHEBI:57912
      The L-enantiomer of tryptophan. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:16828
      The L-enantiomer of tryptophanyl radical. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:32712
    • Compound Source:

      (1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate + L-serine = L-tryptophan + D-glyceraldehyde 3-phosphate + H2O PlantCyc TRP
      Aegilops tauschii PlantCyc TRP
      Amaranthus hypochondriacus PlantCyc TRP
      Amborella trichopoda PlantCyc TRP
      Anacardium occidentale PlantCyc TRP
      Ananas comosus PlantCyc TRP
      Aquilegia coerulea PlantCyc TRP
      Arabidopsis halleri PlantCyc TRP
      Arabidopsis lyrata PlantCyc TRP
      Arabidopsis thaliana col PlantCyc TRP
      Asparagus officinalis PlantCyc TRP
      Beta vulgaris subsp. vulgaris PlantCyc TRP
      beta-carboline biosynthesis PlantCyc TRP
      Boechera stricta PlantCyc TRP
      Brachypodium distachyon PlantCyc TRP
      Brassica napus PlantCyc TRP
      Brassica oleracea var. capitata PlantCyc TRP
      Brassica oleracea var. oleracea PlantCyc TRP
      Brassica rapa FPsc PlantCyc TRP
      Brassica rapa subsp. pekinensis PlantCyc TRP
      Calotropis gigantea PlantCyc TRP
      camalexin biosynthesis PlantCyc TRP
      Camptotheca acuminata PlantCyc TRP
      camptothecin biosynthesis PlantCyc TRP
      Cannabis sativa PlantCyc TRP
      Capsella grandiflora PlantCyc TRP
      Capsella rubella PlantCyc TRP
      Capsicum annuum PlantCyc TRP
      Carica papaya PlantCyc TRP
      Catharanthus roseus PlantCyc TRP
      Chenopodium quinoa PlantCyc TRP
      Chlamydomonas reinhardtii PlantCyc TRP
      Chromochloris zofingiensis PlantCyc TRP
      Cicer arietinum PlantCyc TRP
      Citrus clementina PlantCyc TRP
      Citrus sinensis PlantCyc TRP
      Coccomyxa subellipsoidea C-169 PlantCyc TRP
      Corchorus capsularis PlantCyc TRP
      Cucumis sativus PlantCyc TRP
      Daucus carota subsp. sativus PlantCyc TRP
      Dianthus caryophyllus PlantCyc TRP
      Dioscorea rotundata PlantCyc TRP
      Eucalyptus grandis PlantCyc TRP
      Eutrema salsugineum PlantCyc TRP
      Fragaria vesca subsp. vesca PlantCyc TRP
      glucosinolate biosynthesis from tryptophan PlantCyc TRP
      Glycine max PlantCyc TRP
      Gossypium raimondii PlantCyc TRP
      gramine biosynthesis PlantCyc TRP
      Helianthus annuus PlantCyc TRP
      Hordeum vulgare subsp. vulgare PlantCyc TRP
      Humulus lupulus var. lupulus PlantCyc TRP
      hydroxycinnamic acid serotonin amides biosynthesis PlantCyc TRP
      indole-3-acetate biosynthesis I PlantCyc TRP
      indole-3-acetate biosynthesis II PlantCyc TRP
      indole-3-acetate biosynthesis III (bacteria) PlantCyc TRP
      Kalanchoe fedtschenkoi PlantCyc TRP
      Kalanchoe laxiflora PlantCyc TRP
      Leersia perrieri PlantCyc TRP
      Linum usitatissimum PlantCyc TRP
      Lotus japonicus PlantCyc TRP
      L-tryptophan + 2 NADPH + 2 oxygen + 2 H+ -> (E)-(indol-3-yl)acetaldehyde oxime + CO2 + 2 NADP+ + 3 H2O PlantCyc TRP
      L-tryptophan + H2O -> indole + pyruvate + ammonium PlantCyc TRP
      L-tryptophan biosynthesis PlantCyc TRP
      L-tryptophan degradation to 2-amino-3-carboxymuconate semialdehyde PlantCyc TRP
      L-tryptophan degradation VI (via tryptamine) PlantCyc TRP
      Malus domestica PlantCyc TRP
      Manihot esculenta PlantCyc TRP
      Marchantia polymorpha PlantCyc TRP
      Medicago truncatula PlantCyc TRP
      Micromonas commoda RCC299 PlantCyc TRP
      Micromonas pusilla CCMP1545 PlantCyc TRP
      Mimulus guttatus PlantCyc TRP
      Miscanthus sinensis PlantCyc TRP
      Musa acuminata PlantCyc TRP
      Nicotiana tabacum PlantCyc TRP
      Olea europaea var. sylvestris PlantCyc TRP
      Oropetium thomaeum PlantCyc TRP
      Oryza brachyantha PlantCyc TRP
      Oryza glaberrima PlantCyc TRP
      Oryza punctata PlantCyc TRP
      Oryza rufipogon PlantCyc TRP
      Oryza sativa Japonica Group PlantCyc TRP
      Ostreococcus lucimarinus PlantCyc TRP
      Panicum hallii PlantCyc TRP
      Panicum virgatum PlantCyc TRP
      Petunia axillaris PlantCyc TRP
      Phaseolus vulgaris PlantCyc TRP
      Physcomitrella patens PlantCyc TRP
      Populus trichocarpa PlantCyc TRP
      Prunus persica PlantCyc TRP
      Ricinus communis PlantCyc TRP
      Rosa chinensis PlantCyc TRP
      Rosa multiflora PlantCyc TRP
      Salvia miltiorrhiza PlantCyc TRP
      secologanin and strictosidine biosynthesis PlantCyc TRP
      Selaginella moellendorffii PlantCyc TRP
      serotonin and melatonin biosynthesis PlantCyc TRP
      Setaria italica PlantCyc TRP
      Setaria viridis PlantCyc TRP
      Solanum lycopersicum PlantCyc TRP
      Solanum melongena PlantCyc TRP
      Solanum pennellii PlantCyc TRP
      Solanum tuberosum PlantCyc TRP
      Sorghum bicolor PlantCyc TRP
      Sphagnum fallax PlantCyc TRP
      Spinacia oleracea PlantCyc TRP
      Spirodela polyrhiza PlantCyc TRP
      Thellungiella parvula PlantCyc TRP
      Theobroma cacao PlantCyc TRP
      Trifolium pratense PlantCyc TRP
      Triticum aestivum PlantCyc TRP
      Triticum urartu PlantCyc TRP
      Vitis vinifera PlantCyc TRP
      Volvox carteri PlantCyc TRP
      Zea mays subsp. mays PlantCyc TRP
      Zostera marina PlantCyc TRP
    • Bio Activity:

      2-oxoglutarate + L-tryptophan -> L-glutamate + (indol-3-yl)pyruvate PlantCyc TRP
      indole + L-serine -> L-tryptophan + H2O PlantCyc TRP
      L-serine + indole -> L-tryptophan + H2O PlantCyc TRP
      L-tryptophan -> 3-(aminomethyl)indole PlantCyc TRP
      L-tryptophan -> indole + 2-aminoprop-2-enoate PlantCyc TRP
      L-tryptophan + (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin + oxygen -> 5-hydroxy-L-tryptophan + (6R)-4a-hydroxy-tetrahydrobiopterin PlantCyc TRP
      L-tryptophan + H+ -> CO2 + tryptamine PlantCyc TRP
      L-tryptophan + NADPH + oxygen -> N2-hydroxy-L-tryptophan + NADP+ + H2O PlantCyc TRP
      L-tryptophan + oxygen -> (indol-3-yl)acetamide + CO2 + H2O PlantCyc TRP
      L-tryptophan + oxygen -> N-formylkynurenine PlantCyc TRP
      L-tryptophan + pyruvate <--> L-alanine + (indol-3-yl)pyruvate PlantCyc TRP

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

Density: 1.4±0.1 g/cm3
Boiling Point: 447.9±35.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.1 mmHg at 25°C
Enthalpy of Vaporization: 74.4±3.0 kJ/mol
Flash Point: 224.7±25.9 °C
Index of Refraction: 1.698
Molar Refractivity: 57.8±0.3 cm3
#H bond acceptors: 4
#H bond donors: 4
#Freely Rotating Bonds: 3
#Rule of 5 Violations: 0
ACD/LogP: 1.04
ACD/LogD (pH 5.5): -1.06
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -1.06
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 79 Å2
Polarizability: 22.9±0.5 10-24cm3
Surface Tension: 71.2±3.0 dyne/cm
Molar Volume: 149.9±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) =  -1.22
    Log Kow (Exper. database match) =  -1.05
       Exper. Ref:  Hansch,C et al. (1995)
    Log Kow (Exper. database match) =  -1.06
       Exper. Ref:  Hansch,C et al. (1995)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  432.24  (Adapted Stein & Brown method)
    Melting Pt (deg C):  278.99  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.94E-009  (Modified Grain method)
    MP  (exp database):  282-85 dec deg C
    Subcooled liquid VP: 1.35E-006 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):  2848
       log Kow used: -1.06 (expkow database)
       no-melting pt equation used
     Water Sol (Exper. database match) =  1.34e+004 mg/L (25 deg C)
        Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1046.4 mg/L
    Wat Sol (Exper. database match) =  13400.00
       Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.98E-014  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.830E-013 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -1.06  (exp database)
  Log Kaw used:  -12.092  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  11.032
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.9315
   Biowin2 (Non-Linear Model)     :   0.9197
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   3.0620  (weeks       )
   Biowin4 (Primary Survey Model) :   3.9134  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.2537
   Biowin6 (MITI Non-Linear Model):   0.1049
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.4354
 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):  0.00018 Pa (1.35E-006 mm Hg)
  Log Koa (Koawin est  ): 11.032
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.0167 
       Octanol/air (Koa) model:  0.0264 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.376 
       Mackay model           :  0.571 
       Octanol/air (Koa) model:  0.679 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 239.3126 E-12 cm3/molecule-sec
      Half-Life =     0.045 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.536 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.474 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  368.7
      Log Koc:  2.567 

 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: -1.06 (expkow database)

 Volatilization from Water:
    Henry LC:  1.98E-014 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 4.226E+010  hours   (1.761E+009 days)
    Half-Life from Model Lake :  4.61E+011  hours   (1.921E+010 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       1.13e-006       1.07         1000       
   Water     39              360          1000       
   Soil      61              720          1000       
   Sediment  0.0713          3.24e+003    0          
     Persistence Time: 579 hr




                    

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