ChemSpider 2D Image | Pemetrexed | C20H21N5O6

Pemetrexed

  • Molecular FormulaC20H21N5O6
  • Average mass427.411 Da
  • Monoisotopic mass427.149170 Da
  • ChemSpider ID393879
  • defined stereocentres - 1 of 1 defined stereocentres


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137281-23-3 [RN]
Acide N-{4-[2-(2-amino-4-oxo-4,7-dihydro-1H-pyrrolo[2,3-d]pyrimidin-5-yl)éthyl]benzoyl}-L-glutamique [French] [ACD/IUPAC Name]
L-Glutamic acid, N-(4-(2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo(2,3-d)pyrimidin-5-yl)ethyl)benzoyl)-
L-Glutamic acid, N-[4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]- [ACD/Index Name]
L-glutamic acid, N-[4-[2-(2-amino-4,7-dihydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]-
N-[4-[2-(2-Amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]-L-glutamic Acid
n-[4-[2-(2-amino-4,7-dihydro-4-oxo-3h-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]l-glutamic acid
N-{4-[2-(2-Amino-4-oxo-4,7-dihydro-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl}-L-glutamic acid [ACD/IUPAC Name]
N-{4-[2-(2-Amino-4-oxo-4,7-dihydro-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl}-L-glutaminsäure [German] [ACD/IUPAC Name]
N-{4-[2-(2-Amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl}-L-glutamic acid
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

CHEBI:63616 [DBID]
LY 231514 [DBID]
LY-231514 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      IRRITANT Matrix Scientific 076054
    • Bio Activity:

      Antifolate MedChem Express HY-10820
      Cell Cycle/DNA Damage MedChem Express HY-10820
      Cell Cycle/DNA Damage; MedChem Express HY-10820
      High affinity dihydrofolate reductase inhibitor (Ki = 7 nM). Also inhibits thymidylate synthase, AICART and glycinamide ribonucleotide formyltransferase (Ki values are 109 nM, and 3.5 muM and 9.3 muM, respectively). Indirectly activates AMPK. Inhibits proliferation of cancer cell lines in vitro. Tocris Bioscience 6185
      Pemetrexed is a novel antifolate and antimetabolite for TS, DHFR and GARFT with Ki of 1.3 nM, 7.2 nM and 65 nM, respectively. MedChem Express
      Pemetrexed is a novel antifolate and antimetabolite for TS, DHFR and GARFT with Ki of 1.3 nM, 7.2 nM and 65 nM, respectively.; IC50 Value: 1.3nM(Ki for TS); 7.2nM(DHFR); 65nM(GARFT); Target: Antifolate; in vitro: The Ki values of the pentaglutamate of LY231514 are 1.3, 7.2, and 65 nM for inhibition against TS, DHFR, and GARFT, respectively. MedChem Express HY-10820
      Pemetrexed is a novel antifolate and antimetabolite for TS, DHFR and GARFT with Ki of 1.3 nM, 7.2 nM and 65 nM, respectively.;IC50 Value: 1.3nM(Ki for TS); 7.2nM(DHFR); 65nM(GARFT);Target: Antifolate;In vitro: The Ki values of the pentaglutamate of LY231514 are 1.3, 7.2, and 65 nM for inhibition against TS, DHFR, and GARFT, respectively. In contrast, although a similar high level of inhibitory potency was observed for the parent monoglutamate against DHFR (7.0 nM), the inhibition constants (Ki) for the parent monoglutamate are significantly weaker for TS (109 nM) and GARFT(9,300 nM).The parent monoglutamate LY231514 inhibited rhTS with a Ki of 109 nM when the monoglutamated form of the substrate (6R-MTHF) (6[R]-5,l0-meth ylenetetrahydrofolate) was used. This is in good agreement with the Ki value generated earlier for rmTS (Ki= 340 nM)[1].;In vivo: pemetrexed effectively reduces kidney uptake of radiofolates not only in xenografted mice but also ina syngeneic tumor mouse model[2], MedChem Express HY-10820

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

Density: 1.6±0.1 g/cm3
Boiling Point:
Vapour Pressure:
Enthalpy of Vaporization:
Flash Point:
Index of Refraction: 1.724
Molar Refractivity: 106.3±0.5 cm3
#H bond acceptors: 11
#H bond donors: 7
#Freely Rotating Bonds: 9
#Rule of 5 Violations: 2
ACD/LogP: -0.03
ACD/LogD (pH 5.5): -2.49
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -4.47
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 187 Å2
Polarizability: 42.1±0.5 10-24cm3
Surface Tension: 72.6±7.0 dyne/cm
Molar Volume: 268.1±7.0 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) =  -0.16

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  837.37  (Adapted Stein & Brown method)
    Melting Pt (deg C):  349.84  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  6E-021  (Modified Grain method)
    Subcooled liquid VP: 3.07E-017 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):  138.7
       log Kow used: -0.16 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1.7437e+005 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.08E-029  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  2.433E-023 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -0.16  (KowWin est)
  Log Kaw used:  -27.070  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  26.910
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.7752
   Biowin2 (Non-Linear Model)     :   0.5409
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.6450  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.9622  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.2503
   Biowin6 (MITI Non-Linear Model):   0.0011
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.4707
 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):  4.09E-015 Pa (3.07E-017 mm Hg)
  Log Koa (Koawin est  ): 26.910
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  7.33E+008 
       Octanol/air (Koa) model:  2E+014 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  1 
       Mackay model           :  1 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 239.4499 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
   Reaction With Nitrate Radicals May Be Important!
   Fraction sorbed to airborne particulates (phi): 1 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  2.291E+004
      Log Koc:  4.360 

 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: -0.16 (estimated)

 Volatilization from Water:
    Henry LC:  2.08E-029 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 5.819E+025  hours   (2.425E+024 days)
    Half-Life from Model Lake : 6.348E+026  hours   (2.645E+025 days)

 Removal In Wastewater Treatment:
    Total removal:               1.85  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.76  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       2.66e-011       1.07         1000       
   Water     46              900          1000       
   Soil      53.9            1.8e+003     1000       
   Sediment  0.0889          8.1e+003     0          
     Persistence Time: 979 hr




                    

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