ChemSpider 2D Image | Mitomycin | C15H18N4O5

Mitomycin

  • Molecular FormulaC15H18N4O5
  • Average mass334.327 Da
  • Monoisotopic mass334.127716 Da
  • ChemSpider ID5544

  • defined stereocentres - 4 of 4 defined stereocentres

More details:

Featured data source
The Merck Index Online

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

Mitomycin [BAN] [INN] [USAN] [USP] [Wiki]
[(1aS,8S,8aR,8bS)-6-Amino-8a-methoxy-5-methyl-4,7-dioxo-1,1a,2,4,7,8,8a,8b-octahydroazireno[2',3':3,4]pyrrolo[1,2-a]indol-8-yl]methyl carbamate [ACD/IUPAC Name]
[(1aS,8S,8aR,8bS)-6-Amino-8a-methoxy-5-methyl-4,7-dioxo-1,1a,2,4,7,8,8a,8b-octahydroazireno[2',3':3,4]pyrrolo[1,2-a]indol-8-yl]methyl hydrogen carbonimidate [ACD/IUPAC Name]
[(1aS,8S,8aR,8bS)-6-Amino-8a-methoxy-5-methyl-4,7-dioxo-1,1a,2,4,7,8,8a,8b-octahydroazireno[2',3':3,4]pyrrolo[1,2-a]indol-8-yl]methylcarbamat [German] [ACD/IUPAC Name]
[(1aS,8S,8aR,8bS)-6-Amino-8a-methoxy-5-methyl-4,7-dioxo-1,1a,2,4,7,8,8a,8b-octahydroazireno[2',3':3,4]pyrrolo[1,2-a]indol-8-yl]methylhydrogenkohlenstoffimidat [German] [ACD/IUPAC Name]
[(4S,6S,7R,8S)-11-amino-7-methoxy-12-methyl-10,13-dioxo-2,5-diazatetracyclo[7.4.0.0²,?.0?,?]trideca-1(9),11-dien-8-yl]methyl carbamate
[1aS-(1aa,8b,8aa,8ba)]-6-Amino-8-[[(aminocarbonyl)oxy]methyl]-1,1a,2,8,8a,8b-hexahydro-8a-methoxy-5-methylazirino[2',3':3,4]pyrrolo[1,2-a]indole-4,7-dione
200-008-6 [EINECS]
50-07-7 [RN]
50SG953SK6
More...

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

3043 [DBID]
7231816 [DBID]
CN0700000 [DBID]
50-07-77 [DBID]
AI3-26199 [DBID]
AIDS031090 [DBID]
AIDS-031090 [DBID]
Bio1_000213 [DBID]
Bio1_000702 [DBID]
Bio1_001191 [DBID]
More...
  • Experimental Physico-chemical Properties

    • Experimental Melting Point:

      360 °C (Decomposes) Jean-Claude Bradley Open Melting Point Dataset 17168
      360 °C Indofine [BIO-268]

    • Experimental Solubility:

      .; H2O: 4 mL/vial Stock solutions should be filter sterilized and stored at 2-8 ?C in the dark., clear to slightly hazy, blue to purple Indofine [BIO-268]
      DMSO MedChem Express HY-13316
      in DMSO > 10 mM MedChem Express HY-13316
      Soluble in DMSO (100 mM) and water (5 mM) Hello Bio HB4458
      Soluble to 5 mM in water and to 100 mM in DMSO Tocris Bioscience 3258
  • Miscellaneous

    • Appearance:

      blue-gray Indofine [BIO-268]
      dark blue grey crystalline powder OU Chemical Safety Data (No longer updated) More details

    • Stability:

      Stable. Incompatible with strong acids, strong bases, strongoxidizing agents. OU Chemical Safety Data (No longer updated) More details

    • Toxicity:

      Organic Compound; Amine; Ether; Amide; Ester; Drug; Nucleic Acid Synthesis Inhibitor; Antibiotic, Antineoplastic; Alkylating Agent; Cross-Linking Reagent; Metabolite; Synthetic Compound Toxin, Toxin-Target Database T3D2743
      ORL-RAT LD50 30 mg kg-1, IPR-RAT LD50 2 mg kg-1, IVN-RAT LD50 3 mg kg-1, IVN-DOG LD50 1 mg kg-1 OU Chemical Safety Data (No longer updated) More details

    • Safety:

      Safety glasses, gloves, good ventilation. OU Chemical Safety Data (No longer updated) More details

    • Bio Activity:

      <p>Inhibits proliferation of various cell types. Inhibits DNA synthesis by forming covalent crosslinks between complementary DNA strands.</p> <p><br />Widely used for treatment of feeder cell layers (e.g. for PMEF (primary mouse embryonic fibroblasts) and CD1 mouse embryonic fibroblasts (MEFs) and hESCs (human embryonic stem cells).</p> <p><br />Also shows antitumor activity.</p> Hello Bio HB4458
      ADCs cytotoxin MedChem Express HY-13316
      ADCs cytotoxin DNA alkylator/crosslinker MedChem Express HY-13316
      Antibiotic and antitumor agent. Covalently binds DNA forming intra- and interstrand crosslinks. Inhibits DNA synthesis. Tocris Bioscience 3258
      Antibiotic and antitumor agent. Covalently binds DNA forming intra- and interstrand crosslinks. Inhibits DNA synthesis. Also used for MEF/STO feeder layer preparation in stem cell culture. Tocris Bioscience 3258
      Antibiotic. DNA synthesis inhibitor. Hello Bio HB4458
      Antibiotics Hello Bio HB4458
      Antibody-drug conjugates/ADCs Related MedChem Express HY-13316
      Antibody-drug conjugates/ADCs Related; Cell Cycle/DNA Damage; MedChem Express HY-13316
      Apoptosis Tocris Bioscience 3258
      Apoptosis Inducers Tocris Bioscience 3258
      Cell Biology Tocris Bioscience 3258
      DNA cross-linking antitumor agent Tocris Bioscience 3258
      Mitomycin C is a DNA crosslinking agent that inhibits DNA synthesis and induces apoptosis in a variety of cells.; IC50 Value: 0.14 ?M (EC50, Cytotoxicity against PC3 cells ); Target: DNA alkylator; ADCs toxin; Mitomycin C is part of a family of azidine natural products. MedChem Express HY-13316

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

Density: 1.6±0.1 g/cm3
Boiling Point: 581.8±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.6 mmHg at 25°C
Enthalpy of Vaporization: 87.0±3.0 kJ/mol
Flash Point: 305.6±30.1 °C
Index of Refraction: 1.680
Molar Refractivity: 80.8±0.4 cm3
#H bond acceptors: 9
#H bond donors: 5
#Freely Rotating Bonds: 4
#Rule of 5 Violations: 1
ACD/LogP: -0.49
ACD/LogD (pH 5.5): -0.51
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 10.86
ACD/LogD (pH 7.4): -0.36
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 15.07
Polar Surface Area: 147 Å2
Polarizability: 32.0±0.5 10-24cm3
Surface Tension: 77.3±5.0 dyne/cm
Molar Volume: 213.7±5.0 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) =  -1.18
    Log Kow (Exper. database match) =  -0.40
       Exper. Ref:  Hansch,C et al. (1995)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  487.40  (Adapted Stein & Brown method)
    Melting Pt (deg C):  206.71  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  4.45E-011  (Modified Grain method)
    MP  (exp database):  >360 deg C
    BP  (exp database):  534 deg C
    Subcooled liquid VP: 3.75E-009 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):  8430
       log Kow used: -0.40 (expkow database)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1e+006 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Aliphatic Amines
       Aziridines
       Esters
       Quinone/Hydroquinone

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.14E-024  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  2.322E-015 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -0.40  (exp database)
  Log Kaw used:  -22.332  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  21.932
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.2527
   Biowin2 (Non-Linear Model)     :   0.0011
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.9420  (months      )
   Biowin4 (Primary Survey Model) :   3.1499  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.0676
   Biowin6 (MITI Non-Linear Model):   0.0029
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.3943
 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):  5E-007 Pa (3.75E-009 mm Hg)
  Log Koa (Koawin est  ): 21.932
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  6 
       Octanol/air (Koa) model:  2.1E+009 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.995 
       Mackay model           :  0.998 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  71.8764 E-12 cm3/molecule-sec
      Half-Life =     0.149 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.786 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     2.275000 E-17 cm3/molecule-sec
      Half-Life =     0.504 Days (at 7E11 mol/cm3)
      Half-Life =     12.090 Hrs
   Fraction sorbed to airborne particulates (phi): 0.997 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  13.29
      Log Koc:  1.123 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
  Total Kb for pH > 8 at 25 deg C :  6.602E-005  L/mol-sec
  Kb Half-Life at pH 8:     332.653  years  
  Kb Half-Life at pH 7:    3326.534  years  

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 0.500 (BCF = 3.162)
       log Kow used: -0.40 (expkow database)

 Volatilization from Water:
    Henry LC:  1.14E-024 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 9.391E+020  hours   (3.913E+019 days)
    Half-Life from Model Lake : 1.024E+022  hours   (4.268E+020 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       4.28e-015       2.76         1000       
   Water     49.2            1.44e+003    1000       
   Soil      50.7            2.88e+003    1000       
   Sediment  0.096           1.3e+004     0          
     Persistence Time: 1.18e+003 hr

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