ChemSpider 2D Image | L-Proline | C5H9NO2

L-Proline

  • Molecular FormulaC5H9NO2
  • Average mass115.131 Da
  • Monoisotopic mass115.063332 Da
  • ChemSpider ID128566

  • defined stereocentres - 1 of 1 defined stereocentres

More details:

Featured data source
The Merck Index Online

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

L-Proline [ACD/Index Name] [ACD/IUPAC Name]
(-)-(S)-proline
(−)-(S)-proline
(−)-2-pyrrolidinecarboxylic acid
(-)-2-Pyrrolidinecarboxylic acid
(−)-proline
(-)-Proline
(2S)-2-Pyrrolidincarbonsäure [German]
(2S)-2-Pyrrolidinecarboxylic acid
(2S)-proline
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

3318 [DBID]
6169 [DBID]
9DLQ4CIU6V [DBID]
MFCD00064318 [DBID]
TW3584000 [DBID]
608998_ALDRICH [DBID]
81709_FLUKA [DBID]
81710_FLUKA [DBID]
AI3-26710 [DBID]
AIDS018625 [DBID]
More...
  • References
  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Appearance:

      solid OU Chemical Safety Data (No longer updated) More details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 OU Chemical Safety Data (No longer updated) More details

    • Safety:

      Minimize exposure. OU Chemical Safety Data (No longer updated) More details
      WARNING: Not for human consumption, may irriate skin & eyes. Alfa Aesar A10199
      WARNING: Not sold for human treatment, trials or use Alfa Aesar A10199

    • Chemical Class:

      Pyrrolidine in which the <ital>pro</ital>-<stereo>S</stereo> hydrogen at position 2 is substituted by a carboxylic acid group. <stereo>L</stereo>-Proline is the only one of the twenty DNA-encoded amin o acids which has a secondary amino group <locant>alpha</locant> to the carboxyl group. It is an essential component of collagen and is important for proper functioning of joints and tendons. It also helps maintain and strengthen heart muscles. ChEBI CHEBI:17203, CHEBI:60039
      Pyrrolidine in which the pro-S hydrogen at position 2 is substituted by a carboxylic acid group. L-Proline is the only one of the twenty DNA-encoded amin; o acids which has a secondary amino group alp ha to the carboxyl group. It is an essential component of collagen and is important for proper functioning of joints and tendons. It also ; helps maintain and strengthen heart muscles. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:17203
      Pyrrolidine in which the pro-S hydrogen at position 2 is substituted by a carboxylic acid group. L-Proline is the only one of the twenty DNA-encoded amino acids which has a secondary amino group alpha to the carboxyl group. It is an essential component of collagen and is important for proper functioning of joints and tendons. It also helps maintain and strengthen heart muscles. ChEBI CHEBI:17203
      The zwitterion formed from <stereo>L</stereo>-proline by proton transfer from the carboxy group to the ring nitrogen. It is the predominant species at physiological pH. ChEBI CHEBI:17203, CHEBI:60039
      The zwitterion formed from L-proline by proton transfer from the carboxy group to the ring nitrogen. It is the predominant species at physiological pH. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:60039, CHEBI:60039

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

Density: 1.2±0.1 g/cm3
Boiling Point: 252.2±33.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.1 mmHg at 25°C
Enthalpy of Vaporization: 53.9±6.0 kJ/mol
Flash Point: 106.3±25.4 °C
Index of Refraction: 1.487
Molar Refractivity: 27.9±0.3 cm3
#H bond acceptors: 3
#H bond donors: 2
#Freely Rotating Bonds: 1
#Rule of 5 Violations: 0
ACD/LogP: -0.57
ACD/LogD (pH 5.5): -2.76
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -2.76
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 49 Å2
Polarizability: 11.1±0.5 10-24cm3
Surface Tension: 43.4±3.0 dyne/cm
Molar Volume: 97.0±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) =  -2.15
    Log Kow (Exper. database match) =  -2.54
       Exper. Ref:  Hansch,C et al. (1995)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  414.14  (Adapted Stein & Brown method)
    Melting Pt (deg C):  294.42  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  4.68E-008  (Modified Grain method)
    MP  (exp database):  205 deg C
    Subcooled liquid VP: 3.76E-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):  1.313e+005
       log Kow used: -2.54 (expkow database)
       no-melting pt equation used
     Water Sol (Exper. database match) =  1.62e+005 mg/L (25 deg C)
        Exper. Ref:  MERCK INDEX (1996)

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1.8117e+005 mg/L
    Wat Sol (Exper. database match) =  162000.00
       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 :   1.92E-009  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  5.400E-014 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -2.54  (exp database)
  Log Kaw used:  -7.105  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  4.565
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.9193
   Biowin2 (Non-Linear Model)     :   0.9580
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   3.3338  (days-weeks  )
   Biowin4 (Primary Survey Model) :   4.1105  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.6557
   Biowin6 (MITI Non-Linear Model):   0.6530
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.8796
 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):  0.000501 Pa (3.76E-006 mm Hg)
  Log Koa (Koawin est  ): 4.565
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.00598 
       Octanol/air (Koa) model:  9.02E-009 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.178 
       Mackay model           :  0.324 
       Octanol/air (Koa) model:  7.21E-007 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  82.8185 E-12 cm3/molecule-sec
      Half-Life =     0.129 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.550 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.251 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  4.435
      Log Koc:  0.647 

 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: -2.54 (expkow database)

 Volatilization from Water:
    Henry LC:  1.92E-009 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 3.272E+005  hours   (1.363E+004 days)
    Half-Life from Model Lake :  3.57E+006  hours   (1.487E+005 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       0.0631          3.1          1000       
   Water     35.4            208          1000       
   Soil      64.5            416          1000       
   Sediment  0.0612          1.87e+003    0          
     Persistence Time: 363 hr

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