ChemSpider 2D Image | L-Homocysteine | C4H9NO2S

L-Homocysteine

  • Molecular FormulaC4H9NO2S
  • Average mass135.185 Da
  • Monoisotopic mass135.035400 Da
  • ChemSpider ID82666
  • 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-Homocysteine [ACD/Index Name] [ACD/IUPAC Name]
(2S)-2-amino-4-sulfanylbutanoic acid
(S)-2-amino-4-mercapto-Butanoic acid
(S)-2-Amino-4-mercaptobutanoic acid
(S)-2-Amino-4-mercaptobutyric acid
(S)-homocysteine
227-891-0 [EINECS]
454-28-4 [RN]
6027-13-0 [RN]
D-Homocysteine [ACD/Index Name] [ACD/IUPAC Name]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

0LVT1QZ0BA [DBID]
C00155 [DBID]
CHEBI:17588 [DBID]
H-2800 [DBID]
NSC 118376 [DBID]
NSC 43117 [DBID]
USAF B-12 [DBID]
ZINC00895077 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Appearance:

      white powder OU Chemical Safety Data (No longer updated) More details
      white to slightly beige solid OU Chemical Safety Data (No longer updated) More details
    • Stability:

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 OU Chemical Safety Data (No longer updated) More details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 OU Chemical Safety Data (No longer updated) More details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

      IPR-MUS LD50 500 mg kg-1, IVN-MUS LD50 770 mg kg-1 OU Chemical Safety Data (No longer updated) More details
      Organic Compound; Amine; Metabolite; Uremic Toxin; Natural Compound Toxin, Toxin-Target Database T3D4161
    • Safety:

      GHS07 Biosynth H-2800
      H315; H319; H335 Biosynth H-2800
      Minimize contact. OU Chemical Safety Data (No longer updated) More details
      Minimize exposure. OU Chemical Safety Data (No longer updated) More details
      P261; P280; P312; P302+P352; P304+P340; P305+P351+P338 Biosynth H-2800
      Warning Biosynth H-2800
    • Chemical Class:

      A homocysteine that has L configuration. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:17588
      An amino acid zwitterion arising from transfer of a proton from the carboxy to the amino group of <stereo>L</stereo>-homocysteine; major species at pH 7.3. ChEBI CHEBI:17588, CHEBI:58199
      An amino acid zwitterion arising from transfer of a proton from the carboxy to the amino group of L-homocysteine; major species at pH 7.3. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:58199
      Homocysteine with <stereo>L</stereo> configuration. ChEBI CHEBI:17588, CHEBI:58199
    • Compound Source:

      Aegilops tauschii PlantCyc HOMO-CYS
      Amaranthus hypochondriacus PlantCyc HOMO-CYS
      Amborella trichopoda PlantCyc HOMO-CYS
      Anacardium occidentale PlantCyc HOMO-CYS
      Ananas comosus PlantCyc HOMO-CYS
      Aquilegia coerulea PlantCyc HOMO-CYS
      Arabidopsis halleri PlantCyc HOMO-CYS
      Arabidopsis lyrata PlantCyc HOMO-CYS
      Arabidopsis thaliana col PlantCyc HOMO-CYS
      Asparagus officinalis PlantCyc HOMO-CYS
      Beta vulgaris subsp. vulgaris PlantCyc HOMO-CYS
      Boechera stricta PlantCyc HOMO-CYS
      Brachypodium distachyon PlantCyc HOMO-CYS
      Brassica napus PlantCyc HOMO-CYS
      Brassica oleracea var. capitata PlantCyc HOMO-CYS
      Brassica oleracea var. oleracea PlantCyc HOMO-CYS
      Brassica rapa FPsc PlantCyc HOMO-CYS
      Brassica rapa subsp. pekinensis PlantCyc HOMO-CYS
      Calotropis gigantea PlantCyc HOMO-CYS
      Camptotheca acuminata PlantCyc HOMO-CYS
      Cannabis sativa PlantCyc HOMO-CYS
      Capsella grandiflora PlantCyc HOMO-CYS
      Capsella rubella PlantCyc HOMO-CYS
      Capsicum annuum PlantCyc HOMO-CYS
      Carica papaya PlantCyc HOMO-CYS
      Catharanthus roseus PlantCyc HOMO-CYS
      Chenopodium quinoa PlantCyc HOMO-CYS
      Chlamydomonas reinhardtii PlantCyc HOMO-CYS
      Chromochloris zofingiensis PlantCyc HOMO-CYS
      Cicer arietinum PlantCyc HOMO-CYS
      Citrus clementina PlantCyc HOMO-CYS
      Citrus sinensis PlantCyc HOMO-CYS
      Coccomyxa subellipsoidea C-169 PlantCyc HOMO-CYS
      Corchorus capsularis PlantCyc HOMO-CYS
      Cucumis sativus PlantCyc HOMO-CYS
      Daucus carota subsp. sativus PlantCyc HOMO-CYS
      Dianthus caryophyllus PlantCyc HOMO-CYS
      Dioscorea rotundata PlantCyc HOMO-CYS
      Eucalyptus grandis PlantCyc HOMO-CYS
      Eutrema salsugineum PlantCyc HOMO-CYS
      folate transformations II PlantCyc HOMO-CYS
      Fragaria vesca subsp. vesca PlantCyc HOMO-CYS
      Glycine max PlantCyc HOMO-CYS
      Gossypium raimondii PlantCyc HOMO-CYS
      Helianthus annuus PlantCyc HOMO-CYS
      homocysteine and cysteine interconversion PlantCyc HOMO-CYS
      Hordeum vulgare subsp. vulgare PlantCyc HOMO-CYS
      Humulus lupulus var. lupulus PlantCyc HOMO-CYS
      Kalanchoe fedtschenkoi PlantCyc HOMO-CYS
      Kalanchoe laxiflora PlantCyc HOMO-CYS
      L-cystathionine + H2O -> ammonium + pyruvate + L-homocysteine PlantCyc HOMO-CYS
      L-cysteine biosynthesis III (from L-homocysteine) PlantCyc HOMO-CYS
      Leersia perrieri PlantCyc HOMO-CYS
      L-homocysteine + H2O -> hydrogen sulfide + 2-oxobutanoate + ammonium PlantCyc HOMO-CYS
      Linum usitatissimum PlantCyc HOMO-CYS
      L-methionine biosynthesis II PlantCyc HOMO-CYS
      L-methionine degradation I (to L-homocysteine) PlantCyc HOMO-CYS
      Lotus japonicus PlantCyc HOMO-CYS
      Malus domestica PlantCyc HOMO-CYS
      Manihot esculenta PlantCyc HOMO-CYS
      Marchantia polymorpha PlantCyc HOMO-CYS
      Medicago truncatula PlantCyc HOMO-CYS
      Micromonas commoda RCC299 PlantCyc HOMO-CYS
      Micromonas pusilla CCMP1545 PlantCyc HOMO-CYS
      Mimulus guttatus PlantCyc HOMO-CYS
      Miscanthus sinensis PlantCyc HOMO-CYS
      Musa acuminata PlantCyc HOMO-CYS
      Nicotiana tabacum PlantCyc HOMO-CYS
      Olea europaea var. sylvestris PlantCyc HOMO-CYS
      Oropetium thomaeum PlantCyc HOMO-CYS
      Oryza brachyantha PlantCyc HOMO-CYS
      Oryza glaberrima PlantCyc HOMO-CYS
      Oryza punctata PlantCyc HOMO-CYS
      Oryza rufipogon PlantCyc HOMO-CYS
      Oryza sativa Japonica Group PlantCyc HOMO-CYS
      Ostreococcus lucimarinus PlantCyc HOMO-CYS
      Panicum hallii PlantCyc HOMO-CYS
      Panicum virgatum PlantCyc HOMO-CYS
      Petunia axillaris PlantCyc HOMO-CYS
      Phaseolus vulgaris PlantCyc HOMO-CYS
      Physcomitrella patens PlantCyc HOMO-CYS
      Populus trichocarpa PlantCyc HOMO-CYS
      Prunus persica PlantCyc HOMO-CYS
      Ricinus communis PlantCyc HOMO-CYS
      Rosa chinensis PlantCyc HOMO-CYS
      Rosa multiflora PlantCyc HOMO-CYS
      S-adenosyl-L-methionine cycle II PlantCyc HOMO-CYS
      Salvia miltiorrhiza PlantCyc HOMO-CYS
      Selaginella moellendorffii PlantCyc HOMO-CYS
      Setaria italica PlantCyc HOMO-CYS
      Setaria viridis PlantCyc HOMO-CYS
      S-methyl-L-methionine cycle PlantCyc HOMO-CYS
      Solanum lycopersicum PlantCyc HOMO-CYS
      Solanum melongena PlantCyc HOMO-CYS
      Solanum pennellii PlantCyc HOMO-CYS
      Solanum tuberosum PlantCyc HOMO-CYS
      Sorghum bicolor PlantCyc HOMO-CYS
      Sphagnum fallax PlantCyc HOMO-CYS
      Spinacia oleracea PlantCyc HOMO-CYS
      Spirodela polyrhiza PlantCyc HOMO-CYS
      Thellungiella parvula PlantCyc HOMO-CYS
      Theobroma cacao PlantCyc HOMO-CYS
      Trifolium pratense PlantCyc HOMO-CYS
      Triticum aestivum PlantCyc HOMO-CYS
      Triticum urartu PlantCyc HOMO-CYS
      Vitis vinifera PlantCyc HOMO-CYS
      Volvox carteri PlantCyc HOMO-CYS
      Zea mays subsp. mays PlantCyc HOMO-CYS
      Zostera marina PlantCyc HOMO-CYS
    • Bio Activity:

      L-cystathionine -> 2-aminoprop-2-enoate + L-homocysteine PlantCyc HOMO-CYS
      L-homocysteine -> hydrogen sulfide + (2Z)-2-aminobut-2-enoate + H+ PlantCyc HOMO-CYS
      L-homocysteine + 5-methyltetrahydropteroyl tri-L-glutamate -> L-methionine + tetrahydropteroyl tri-L-glutamate PlantCyc HOMO-CYS
      L-homocysteine + a 5-methyltetrahydrofolate -> L-methionine + a tetrahydrofolate PlantCyc HOMO-CYS
      L-homocysteine + L-serine -> L-cystathionine + H2O PlantCyc HOMO-CYS
      L-serine + L-homocysteine -> L-cystathionine + H2O PlantCyc HOMO-CYS
      S-adenosyl-L-homocysteine + H2O <--> L-homocysteine + adenosine PlantCyc HOMO-CYS
      S-adenosyl-L-homocysteine + H2O -> L-homocysteine + adenosine PlantCyc HOMO-CYS
      S-adenosyl-L-methionine + L-homocysteine -> L-methionine + S-adenosyl-L-homocysteine + H+ PlantCyc HOMO-CYS
      S-adenosyl-L-methionine + L-homocysteine -> S-adenosyl-L-homocysteine + L-methionine + H+ PlantCyc HOMO-CYS
      S-methyl-L-methionine + L-homocysteine -> 2 L-methionine + H+ PlantCyc HOMO-CYS

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

Density: 1.3±0.1 g/cm3
Boiling Point: 299.7±35.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.3 mmHg at 25°C
Enthalpy of Vaporization: 59.4±6.0 kJ/mol
Flash Point: 135.0±25.9 °C
Index of Refraction: 1.538
Molar Refractivity: 33.5±0.3 cm3
#H bond acceptors: 3
#H bond donors: 3
#Freely Rotating Bonds: 3
#Rule of 5 Violations: 0
ACD/LogP: 0.22
ACD/LogD (pH 5.5): -2.44
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -2.44
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 102 Å2
Polarizability: 13.3±0.5 10-24cm3
Surface Tension: 54.4±3.0 dyne/cm
Molar Volume: 107.3±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) =  -2.56

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  360.24  (Adapted Stein & Brown method)
    Melting Pt (deg C):  209.42  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  4.4E-007  (Modified Grain method)
    MP  (exp database):  232.5 deg C
    Subcooled liquid VP: 7.53E-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):  1.136e+005
       log Kow used: -2.56 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  48863 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   7.03E-011  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  6.889E-013 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -2.56  (KowWin est)
  Log Kaw used:  -8.542  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  5.982
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.9097
   Biowin2 (Non-Linear Model)     :   0.9449
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   3.2895  (days-weeks  )
   Biowin4 (Primary Survey Model) :   4.0816  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.5726
   Biowin6 (MITI Non-Linear Model):   0.5578
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  1.0863
 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):  0.01 Pa (7.53E-005 mm Hg)
  Log Koa (Koawin est  ): 5.982
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.000299 
       Octanol/air (Koa) model:  2.36E-007 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.0107 
       Mackay model           :  0.0233 
       Octanol/air (Koa) model:  1.88E-005 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  81.0376 E-12 cm3/molecule-sec
      Half-Life =     0.132 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.584 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.017 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  5.073
      Log Koc:  0.705 

 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: -2.56 (estimated)

 Volatilization from Water:
    Henry LC:  7.03E-011 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 9.683E+006  hours   (4.035E+005 days)
    Half-Life from Model Lake : 1.056E+008  hours   (4.401E+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       0.00254         3.17         1000       
   Water     34.5            208          1000       
   Soil      65.4            416          1000       
   Sediment  0.0597          1.87e+003    0          
     Persistence Time: 386 hr




                    

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