ChemSpider 2D Image | melphalan | C13H18Cl2N2O2

melphalan

  • Molecular FormulaC13H18Cl2N2O2
  • Average mass305.200 Da
  • Monoisotopic mass304.074524 Da
  • ChemSpider ID405297
  • defined stereocentres - 1 of 1 defined stereocentres


More details:



Featured data source



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

(2S)-2-Amino-3-{4-[bis(2-chlorethyl)amino]phenyl}propansäure [German]
(2S)-2-amino-3-{4-[bis(2-chloroethyl)amino]phenyl}propanoic acid
148-82-3 [RN]
205-726-3 [EINECS]
3-[p-[Bis(2-chloroethyl)amino]phenyl]-L-alanine
3025 C.B.
4-[Bis(2-chlorethyl)amino]-L-phenylalanin [German] [ACD/IUPAC Name]
4-[Bis(2-chloroethyl)amino]-L-phenylalanine [ACD/IUPAC Name]
4-[Bis(2-chloroéthyl)amino]-L-phénylalanine [French] [ACD/IUPAC Name]
745
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

At 290 [DBID]
CB 3026 [DBID]
AIDS027538 [DBID]
AIDS-027538 [DBID]
AY3675000 [DBID]
BRN 2816456 [DBID]
BSPBio_002407 [DBID]
cb 3025 [DBID]
CB-3025 [DBID]
CCRIS 374 [DBID]
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  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      Danger Biosynth W-108096
      GHS06; GHS08 Biosynth W-108096
      H300; H310; H330; H350; H361 Biosynth W-108096
      L01AA03 Wikidata Q2298283
      P201; P260; P264; P280; P284; P302+P350 Biosynth W-108096
    • Chemical Class:

      A phenylalanine derivative comprising <stereo>L</stereo>-phenylalanine having [bis(2-chloroethyl)amino group at the 4-position on the phenyl ring. ChEBI CHEBI:28876
    • Compound Source:

      synthetic Microsource [01500382]
    • Bio Activity:

      Apoptosis Tocris Bioscience 4619
      Cell Biology Tocris Bioscience 4619
      Cell Cycle/DNA Damage MedChem Express HY-17575
      Cell Cycle/DNA Damage; MedChem Express HY-17575
      DNA alkylating agent; cytotoxic and antineoplastic Tocris Bioscience 4619
      DNA alkylating agent; induces cytotoxicity through the formation of stable interstrand and intrastrand crosslinks within DNA. Inhibits growth of PC-3 cells (IC50 values are 0.074 and 0.77 ?g/ml for se quential dosing and single dosing respectively). Tocris Bioscience 4619
      DNA alkylating agent; induces cytotoxicity through the formation of stable interstrand and intrastrand crosslinks within DNA. Inhibits growth of PC-3 cells (IC50 values are 0.074 and 0.77 ?g/ml for sequential dosing and single dosing respectively). Tocris Bioscience 4619
      DNA alkylating agent; induces cytotoxicity through the formation of stable interstrand and intrastrand crosslinks within DNA. Inhibits growth of PC-3 cells (IC50 values are 0.074 and 0.77 mug/ml for sequential dosing and single dosing respectively). Tocris Bioscience 4619
      DNA alkylator/crosslinker MedChem Express HY-17575
      Melphalan(Sarcolysin; L-PAM) is a chemotherapy drug belonging to the class of nitrogen mustard alkylating agents; attaches the alkyl group to the guanine base of DNA. MedChem Express
      Melphalan(Sarcolysin; L-PAM) is a chemotherapy drug belonging to the class of nitrogen mustard alkylating agents; attaches the alkyl group to the guanine base of DNA.; IC50 value:; Target: DNA alkylator; The agent was first investigated as a possible drug for use in melanoma. MedChem Express HY-17575
      Melphalan(Sarcolysin; L-PAM) is a chemotherapy drug belonging to the class of nitrogen mustard alkylating agents; attaches the alkyl group to the guanine base of DNA.;IC50 value:;Target: DNA alkylator;The agent was first investigated as a possible drug for use in melanoma. It was not found to be effective, but has been found to be effective in the treatment of myeloma. Melphalan is currently being used to treat ocular retinoblastoma, a pediatric solid tumor. This is accomplished via transarterial catheter based slow pulsed infusion into the ophthalmic artery.[ MedChem Express HY-17575
      Other Apoptosis Tocris Bioscience 4619

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

Density: 1.3±0.1 g/cm3
Boiling Point: 473.1±45.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.2 mmHg at 25°C
Enthalpy of Vaporization: 77.6±3.0 kJ/mol
Flash Point: 239.9±28.7 °C
Index of Refraction: 1.597
Molar Refractivity: 78.8±0.3 cm3
#H bond acceptors: 4
#H bond donors: 3
#Freely Rotating Bonds: 8
#Rule of 5 Violations: 0
ACD/LogP: 1.79
ACD/LogD (pH 5.5): -1.05
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -1.03
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 67 Å2
Polarizability: 31.2±0.5 10-24cm3
Surface Tension: 55.2±3.0 dyne/cm
Molar Volume: 231.2±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) =  0.39

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  512.42  (Adapted Stein & Brown method)
    Melting Pt (deg C):  308.76  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  3.03E-010  (Modified Grain method)
    MP  (exp database):  182.5 deg C
    Subcooled liquid VP: 1.33E-008 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):  45.68
       log Kow used: 0.39 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  124.71 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   4.19E-013  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  2.664E-012 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  0.39  (KowWin est)
  Log Kaw used:  -10.766  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  11.156
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.4554
   Biowin2 (Non-Linear Model)     :   0.0072
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.2377  (months      )
   Biowin4 (Primary Survey Model) :   3.2785  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.0601
   Biowin6 (MITI Non-Linear Model):   0.0038
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.4694
 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):  1.77E-006 Pa (1.33E-008 mm Hg)
  Log Koa (Koawin est  ): 11.156
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  1.69 
       Octanol/air (Koa) model:  0.0352 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.984 
       Mackay model           :  0.993 
       Octanol/air (Koa) model:  0.738 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 224.9898 E-12 cm3/molecule-sec
      Half-Life =     0.048 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.570 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.988 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  354.9
      Log Koc:  2.550 

 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: 0.39 (estimated)

 Volatilization from Water:
    Henry LC:  4.19E-013 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 2.441E+009  hours   (1.017E+008 days)
    Half-Life from Model Lake : 2.663E+010  hours   (1.11E+009 days)

 Removal In Wastewater Treatment:
    Total removal:               1.86  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       2.68e-005       1.14         1000       
   Water     47.8            1.44e+003    1000       
   Soil      52.1            2.88e+003    1000       
   Sediment  0.0951          1.3e+004     0          
     Persistence Time: 1.2e+003 hr




                    

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