ChemSpider 2D Image | L-(-)-Serine | C3H7NO3

L-(-)-Serine

  • Molecular FormulaC3H7NO3
  • Average mass105.093 Da
  • Monoisotopic mass105.042595 Da
  • ChemSpider ID5736
  • defined stereocentres - 1 of 1 defined stereocentres


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L-(-)-Serine [Wiki]
(-)-Serine
(2S)-2-Amino-3-hydroxypropansäure [German]
(S)-(-)-serine
(S)-2-amino-3-hydroxypropanoic acid
(S)-2-amino-3-hydroxy-Propanoic acid
(S)-2-Amino-3-hydroxypropionic acid
(S)-a-Amino-b-hydroxypropionic acid
200-274-3 [EINECS]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

452VLY9402 [DBID]
VT8100000 [DBID]
78682_FLUKA [DBID]
84959_FLUKA [DBID]
bmse000048 [DBID]
BRN 1721404 [DBID]
C00065 [DBID]
c0933 [DBID]
CHEBI:17115 [DBID]
CHEBI:33384 [DBID]
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  • Experimental Physico-chemical Properties
  • Predicted Physico-chemical Properties
  • Miscellaneous
    • Toxicity:

      Organic Compound; Amine; Drug; Food Toxin; Dietary Supplement; Micronutrient; Metabolite; Nutraceutical; Household Toxin; Animal Toxin; Natural Compound; Supplement; Non-Essential Amino Acid Toxin, Toxin-Target Database T3D4367
    • Safety:

      IRRITANT Matrix Scientific 076146
      WARNING: Not for human consumption, may irriate skin & eyes. Alfa Aesar A11179
      WARNING: Not sold for human treatment, trials or use Alfa Aesar A11179
    • Chemical Class:

      A serine zwitterion obtained by transfer of a proton from the carboxy to the amino group of <stereo>L</stereo>-serine. ChEBI CHEBI:17115, CHEBI:33384
      A serine zwitterion obtained by transfer of a proton from the carboxy to the amino group of L-serine. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:33384
      The <stereo>L</stereo>-enantiomer of serine. ChEBI CHEBI:17115, CHEBI:33384
      The L-enantiomer of serine. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:17115
    • Compound Source:

      (1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate + L-serine = L-tryptophan + D-glyceraldehyde 3-phosphate + H2O PlantCyc SER
      3 L-serine + 3 2,3-dihydroxybenzoate + 6 ATP -> enterobactin + 6 AMP + 6 diphosphate + 3 H+ PlantCyc SER
      Aegilops tauschii PlantCyc SER
      Amaranthus hypochondriacus PlantCyc SER
      Amborella trichopoda PlantCyc SER
      Anacardium occidentale PlantCyc SER
      Ananas comosus PlantCyc SER
      Aquilegia coerulea PlantCyc SER
      Arabidopsis halleri PlantCyc SER
      Arabidopsis lyrata PlantCyc SER
      Arabidopsis thaliana col PlantCyc SER
      Asparagus officinalis PlantCyc SER
      Beta vulgaris subsp. vulgaris PlantCyc SER
      Boechera stricta PlantCyc SER
      Brachypodium distachyon PlantCyc SER
      Brassica napus PlantCyc SER
      Brassica oleracea var. capitata PlantCyc SER
      Brassica oleracea var. oleracea PlantCyc SER
      Brassica rapa FPsc PlantCyc SER
      Brassica rapa subsp. pekinensis PlantCyc SER
      Calotropis gigantea PlantCyc SER
      Camptotheca acuminata PlantCyc SER
      Cannabis sativa PlantCyc SER
      Capsella grandiflora PlantCyc SER
      Capsella rubella PlantCyc SER
      Capsicum annuum PlantCyc SER
      Carica papaya PlantCyc SER
      Catharanthus roseus PlantCyc SER
      Chenopodium quinoa PlantCyc SER
      Chlamydomonas reinhardtii PlantCyc SER
      choline biosynthesis I PlantCyc SER
      Chromochloris zofingiensis PlantCyc SER
      Cicer arietinum PlantCyc SER
      Citrus clementina PlantCyc SER
      Citrus sinensis PlantCyc SER
      Coccomyxa subellipsoidea C-169 PlantCyc SER
      Corchorus capsularis PlantCyc SER
      Cucumis sativus PlantCyc SER
      Daucus carota subsp. sativus PlantCyc SER
      Dianthus caryophyllus PlantCyc SER
      Dioscorea rotundata PlantCyc SER
      D-serine metabolism PlantCyc SER
      Eucalyptus grandis PlantCyc SER
      Eutrema salsugineum PlantCyc SER
      folate polyglutamylation PlantCyc SER
      folate transformations II PlantCyc SER
      Fragaria vesca subsp. vesca PlantCyc SER
      glycine biosynthesis PlantCyc SER
      glycine biosynthesis I PlantCyc SER
      Glycine max PlantCyc SER
      Gossypium raimondii PlantCyc SER
      Helianthus annuus PlantCyc SER
      homocysteine and cysteine interconversion PlantCyc SER
      Hordeum vulgare subsp. vulgare PlantCyc SER
      Humulus lupulus var. lupulus PlantCyc SER
      Kalanchoe fedtschenkoi PlantCyc SER
      Kalanchoe laxiflora PlantCyc SER
      lathyrine biosynthesis PlantCyc SER
      L-cysteine biosynthesis I PlantCyc SER
      L-cysteine biosynthesis III (from L-homocysteine) PlantCyc SER
      Leersia perrieri PlantCyc SER
      Linum usitatissimum PlantCyc SER
      Lotus japonicus PlantCyc SER
      L-selenocysteine biosynthesis II (archaea and eukaryotes) PlantCyc SER
      L-serine -> pyruvate + ammonium PlantCyc SER
      L-serine + NADP+ -> 2-aminoacetaldehyde + CO2 + NADPH PlantCyc SER
      L-serine biosynthesis PlantCyc SER
      L-tryptophan biosynthesis PlantCyc SER
      Malus domestica PlantCyc SER
      Manihot esculenta PlantCyc SER
      Marchantia polymorpha PlantCyc SER
      Medicago truncatula PlantCyc SER
      Micromonas commoda RCC299 PlantCyc SER
      Micromonas pusilla CCMP1545 PlantCyc SER
      Mimulus guttatus PlantCyc SER
      Miscanthus sinensis PlantCyc SER
      Musa acuminata PlantCyc SER
      Nicotiana tabacum PlantCyc SER
      Olea europaea var. sylvestris PlantCyc SER
      Oropetium thomaeum PlantCyc SER
      Oryza brachyantha PlantCyc SER
      Oryza glaberrima PlantCyc SER
      Oryza punctata PlantCyc SER
      Oryza rufipogon PlantCyc SER
      Oryza sativa Japonica Group PlantCyc SER
      Ostreococcus lucimarinus PlantCyc SER
      Panicum hallii PlantCyc SER
      Panicum virgatum PlantCyc SER
      Petunia axillaris PlantCyc SER
      Phaseolus vulgaris PlantCyc SER
      phosphatidylethanolamine biosynthesis I PlantCyc SER
      phosphatidylethanolamine biosynthesis II PlantCyc SER
      phosphatidylethanolamine biosynthesis III PlantCyc SER
      photorespiration PlantCyc SER
      Physcomitrella patens PlantCyc SER
      Populus trichocarpa PlantCyc SER
      Prunus persica PlantCyc SER
      Ricinus communis PlantCyc SER
      Rosa chinensis PlantCyc SER
      Rosa multiflora PlantCyc SER
      Salvia miltiorrhiza PlantCyc SER
      Selaginella moellendorffii PlantCyc SER
      seleno-amino acid biosynthesis PlantCyc SER
      Setaria italica PlantCyc SER
      Setaria viridis PlantCyc SER
      Solanum lycopersicum PlantCyc SER
      Solanum melongena PlantCyc SER
      Solanum pennellii PlantCyc SER
      Solanum tuberosum PlantCyc SER
      Sorghum bicolor PlantCyc SER
      Sphagnum fallax PlantCyc SER
      sphingolipid biosynthesis (plants) PlantCyc SER
      Spinacia oleracea PlantCyc SER
      Spirodela polyrhiza PlantCyc SER
      superpathway of phospholipid biosynthesis II (plants) PlantCyc SER
      Thellungiella parvula PlantCyc SER
      Theobroma cacao PlantCyc SER
      Trifolium pratense PlantCyc SER
      Triticum aestivum PlantCyc SER
      Triticum urartu PlantCyc SER
      Vitis vinifera PlantCyc SER
      Volvox carteri PlantCyc SER
      Zea mays subsp. mays PlantCyc SER
      Zostera marina PlantCyc SER
    • Bio Activity:

      2-amino-4-carboxypyrimidine + L-serine + H+ -> lathyrine + CO2 + H2O PlantCyc SER
      3-phospho-L-serine + H2O -> L-serine + phosphate PlantCyc SER
      a CDP-diacylglycerol + L-serine -> CMP + a 3-O-sn-phosphatidyl-L-serine + H+ PlantCyc SER
      a CDP-diacylglycerol[endoplasmic reticulum lumen] + L-serine[endoplasmic reticulum lumen] -> CMP[endoplasmic reticulum lumen] + a 3-O-sn-phosphatidyl-L-serine[endoplasmic reticulum lumen] + H+[endoplasmic reticulum lumen] PlantCyc SER
      a tRNAsec + L-serine + ATP -> an L-seryl-[tRNAsec] + AMP + diphosphate PlantCyc SER
      an L-1-phosphatidylethanolamine + L-serine <--> a 3-O-sn-phosphatidyl-L-serine + ethanolamine PlantCyc SER
      an L-1-phosphatidylethanolamine + L-serine -> a 3-O-sn-phosphatidyl-L-serine + ethanolamine PlantCyc SER
      Endogenous agonist at the inhibitory glycine receptor. D-isomer also available. Tocris Bioscience 227
      Endogenous agonist at the inhibitory glycine receptor. D-Serine (Cat. No. 0226) also available. Tocris Bioscience 0227, 227
      Glycine Receptors Tocris Bioscience 227
      glyoxylate + L-serine <--> hydroxypyruvate + glycine PlantCyc SER
      indole + L-serine -> L-tryptophan + H2O PlantCyc SER
      Ion Channels Tocris Bioscience 227
      L-homocysteine + L-serine -> L-cystathionine + H2O PlantCyc SER
      Ligand-gated Ion Channels Tocris Bioscience 227
      L-serine -> 2-aminoprop-2-enoate + H2O PlantCyc SER
      L-serine -> D-serine PlantCyc SER
      L-serine + a tetrahydrofolate <--> glycine + a 5,10-methylene-tetrahydrofolate + H2O PlantCyc SER
      L-serine + acetyl-CoA -> O-acetyl-L-serine + coenzyme A PlantCyc SER
      L-serine + ATP + H+ -> L-seryl-adenylate + diphosphate PlantCyc SER
      L-serine + H+ -> ethanolamine + CO2 PlantCyc SER
      L-serine + indole -> L-tryptophan + H2O PlantCyc SER
      L-serine + L-homocysteine -> L-cystathionine + H2O PlantCyc SER
      L-serine + NADP+ -> 2-aminomalonate semialdehyde + NADPH + H+ PlantCyc SER
      L-serine + palmitoyl-CoA + H+ -> CO2 + 3-dehydrosphinganine + coenzyme A PlantCyc SER
      Weak endogenous glycine receptor agonist Tocris Bioscience 0227, 227

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

Density: 1.4±0.1 g/cm3
Boiling Point: 394.8±32.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.1 mmHg at 25°C
Enthalpy of Vaporization: 74.6±6.0 kJ/mol
Flash Point: 192.6±25.1 °C
Index of Refraction: 1.519
Molar Refractivity: 22.5±0.3 cm3
#H bond acceptors: 4
#H bond donors: 4
#Freely Rotating Bonds: 2
#Rule of 5 Violations: 0
ACD/LogP: -1.58
ACD/LogD (pH 5.5): -3.64
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -3.65
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 84 Å2
Polarizability: 8.9±0.5 10-24cm3
Surface Tension: 72.3±3.0 dyne/cm
Molar Volume: 74.2±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) =  -3.46
    Log Kow (Exper. database match) =  -3.07
       Exper. Ref:  Hansch,C et al. (1995)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  351.87  (Adapted Stein & Brown method)
    Melting Pt (deg C):  218.02  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.97E-008  (Modified Grain method)
    MP  (exp database):  229 dec deg C
    Subcooled liquid VP: 4.61E-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):  4.02e+005
       log Kow used: -3.07 (expkow database)
       no-melting pt equation used
     Water Sol (Exper. database match) =  4.25e+005 mg/L (25 deg C)
        Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)
     Water Sol (Exper. database match) =  3.98e+004 mg/L (20 deg C)
        Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)
     Water Sol (Exper. database match) =  3.64e+005 mg/L (20 deg C)
        Exper. Ref:  BEILSTEIN
     Water Sol (Exper. database match) =  4.32e+004 mg/L (20 deg C)
        Exper. Ref:  BEILSTEIN

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  6.1193e+005 mg/L
    Wat Sol (Exper. database match) =  425000.00
       Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)
    Wat Sol (Exper. database match) =  39800.00
       Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)
    Wat Sol (Exper. database match) =  364000.00
       Exper. Ref:  BEILSTEIN
    Wat Sol (Exper. database match) =  43200.00
       Exper. Ref:  BEILSTEIN

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   5.46E-014  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.022E-014 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -3.07  (exp database)
  Log Kaw used:  -11.651  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  8.581
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.0828
   Biowin2 (Non-Linear Model)     :   0.9877
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   3.5159  (days-weeks  )
   Biowin4 (Primary Survey Model) :   4.2544  (hours-days  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.7738
   Biowin6 (MITI Non-Linear Model):   0.8423
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  1.1930
 Ready Biodegradability Prediction:   YES

Hydrocarbon Biodegradation (BioHCwin v1.01):
    Structure incompatible with current estimation method!

 Sorption to aerosols (25 Dec C)[AEROWIN v1.00]:
  Vapor pressure (liquid/subcooled):  0.000615 Pa (4.61E-006 mm Hg)
  Log Koa (Koawin est  ): 8.581
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.00488 
       Octanol/air (Koa) model:  9.35E-005 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.15 
       Mackay model           :  0.281 
       Octanol/air (Koa) model:  0.00743 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  42.3246 E-12 cm3/molecule-sec
      Half-Life =     0.253 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     3.033 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.215 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  1
      Log Koc:  0.000 

 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: -3.07 (expkow database)

 Volatilization from Water:
    Henry LC:  5.46E-014 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.099E+010  hours   (4.58E+008 days)
    Half-Life from Model Lake : 1.199E+011  hours   (4.997E+009 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       2.64e-006       6.06         1000       
   Water     34.5            208          1000       
   Soil      65.5            416          1000       
   Sediment  0.0596          1.87e+003    0          
     Persistence Time: 387 hr




                    

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