ChemSpider 2D Image | Colchicine | C22H25NO6

Colchicine

  • Molecular FormulaC22H25NO6
  • Average mass399.437 Da
  • Monoisotopic mass399.168182 Da
  • ChemSpider ID5933

  • 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

(1E)-N-[(7S)-1,2,3,10-Tetramethoxy-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl]ethanimidic acid [ACD/IUPAC Name]
(1E)-N-[(7S)-1,2,3,10-Tetramethoxy-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl]ethanimidsäure [German] [ACD/IUPAC Name]
(S)-colchicine
(S)-N-(5,6,7,9-Tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo[a]heptalen-7-yl)acetamide
200-598-5 [EINECS]
2228813 [Beilstein]
64-86-8 [RN]
Acetamide, N-(5,6,7,9-tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo(a)heptalen-7-yl)-, (S)-
Acetamide, N-[(7S)-5,6,7,9-tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo[a]heptalen-7-yl]- [ACD/Index Name]
Acide (1E)-N-[(7S)-1,2,3,10-tétraméthoxy-9-oxo-5,6,7,9-tétrahydrobenzo[a]heptalén-7-yl]éthanimidique [French] [ACD/IUPAC Name]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

CHEBI:27882 [DBID]
GH0700000 [DBID]
SML2Y3J35T [DBID]
AI3-31149 [DBID]
AIDS000216 [DBID]
AIDS-000216 [DBID]
C07592 [DBID]
C3915_SIGMA [DBID]
C9754_SIGMA [DBID]
CCRIS 691 [DBID]
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  • Experimental Physico-chemical Properties
  • Predicted Physico-chemical Properties
  • Miscellaneous

    • Appearance:

      pale yellow crystals or powder OU Chemical Safety Data (No longer updated) More details
      White to yellow with a green cast Indofine [06-013]

    • Stability:

      Stable. Light sensitive. Incompatible with strong oxidizing agents. OU Chemical Safety Data (No longer updated) More details

    • Toxicity:

      Poison. May be fatal if swallowed. Note very low LD50s below. , IPR-RAT LD50 6.1 mg kg-1, IVN-MUS LD50 1.6 mg kg-1, SCU-MUS LD50 1.2 mg kg-1 OU Chemical Safety Data (No longer updated) More details

    • Safety:

      46-28 Alfa Aesar A13240
      53-16-26-28-36/37-45 Alfa Aesar A13240
      DANGER: POISON, irritates skin, eyes, lungs Alfa Aesar A13240
      Safety glasses, gloves, good ventilation. OU Chemical Safety Data (No longer updated) More details

    • Target Organs:

      Microtubule Associated inhibitor TargetMol T0320

    • Chemical Class:

      A colchicine that has (S)-configuration. It is a secondary metabolite, has anti-inflammatory properties and is used to treat gout, crystal-induced joint inflammation, familial Mediterranean fever, and many other conditions. ChEBI CHEBI:27882

    • Compound Source:

      colchicine biosynthesis PlantCyc CPD-9785
      Linum usitatissimum PlantCyc CPD-9785

    • Bio Activity:

      Cell Cycle/Checkpoint TargetMol T0320
      Cell Cycle/DNA Damage MedChem Express HY-16569
      Cell Cycle/DNA Damage; MedChem Express HY-16569
      Colchicine is a tubulin inhibitor, it blocks polymerization of microtubules by binding to tubulin (IC50 = 3.2 ?M). MedChem Express HY-16569
      deacetylcolchicine + acetyl-CoA -> (S)-colchicine + coenzyme A + H+ PlantCyc CPD-9785
      Microtubule/Tubulin MedChem Express HY-16569
      Tubulin beta chain TargetMol T0320
  • Gas Chromatography

    • Retention Index (Kovats):

      3340 (Program type: Isothermal; Col... (show more) umn class: Standard non-polar; Column length: 2 m; Column type: Packed; CAS no: 64868; Active phase: SE-30; Data type: Kovats RI; Authors: Moffat, A.C.; Stead, A.H.; Smalldon, K.W., Optimum use of paper, thin-layer and gas-liquid chromatography for the identification of basic drugs. III. Gas-liquid chromatography, J. Chromatogr., 90, 1974, 19-33.) NIST Spectra nist ri

    • Retention Index (Normal Alkane):

      3340 (Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column type: Other; CAS no: 64868; Active phase: Methyl Silicone; Data type: Normal alkane RI; Authors: Ardrey, R.E.; Moffat, A.C., Gas-liquid chromatographic retention indices of 1318 substances of toxicological interest on SE-30 or OV-1 stationary phase, J. Chromatogr., 220, 1981, 195-252.) NIST Spectra nist ri

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

Density: 1.3±0.1 g/cm3
Boiling Point: 726.0±60.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.4 mmHg at 25°C
Enthalpy of Vaporization: 106.0±3.0 kJ/mol
Flash Point: 392.9±32.9 °C
Index of Refraction: 1.585
Molar Refractivity: 106.6±0.4 cm3
#H bond acceptors: 7
#H bond donors: 1
#Freely Rotating Bonds: 5
#Rule of 5 Violations: 0
ACD/LogP: 0.92
ACD/LogD (pH 5.5): 1.10
ACD/BCF (pH 5.5): 4.06
ACD/KOC (pH 5.5): 94.92
ACD/LogD (pH 7.4): 1.10
ACD/BCF (pH 7.4): 4.06
ACD/KOC (pH 7.4): 94.92
Polar Surface Area: 83 Å2
Polarizability: 42.3±0.5 10-24cm3
Surface Tension: 50.5±5.0 dyne/cm
Molar Volume: 318.1±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) =  1.86
    Log Kow (Exper. database match) =  1.30
       Exper. Ref:  Hansch,C et al. (1995)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  562.47  (Adapted Stein & Brown method)
    Melting Pt (deg C):  241.78  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  3.18E-011  (Modified Grain method)
    MP  (exp database):  156 deg C
    Subcooled liquid VP: 6.95E-010 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):  239.5
       log Kow used: 1.30 (expkow database)
       no-melting pt equation used
     Water Sol (Exper. database match) =  4.5e+004 mg/L (25 deg C)
        Exper. Ref:  SEIDELL,A (1941)

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  50.445 mg/L
    Wat Sol (Exper. database match) =  45000.00
       Exper. Ref:  SEIDELL,A (1941)

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Vinyl/Allyl Ketones
       Vinyl/Allyl Ethers

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.79E-017  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  6.979E-014 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  1.30  (exp database)
  Log Kaw used:  -15.136  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  16.436
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.8774
   Biowin2 (Non-Linear Model)     :   0.9697
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.9819  (months      )
   Biowin4 (Primary Survey Model) :   3.6077  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.3606
   Biowin6 (MITI Non-Linear Model):   0.0415
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.7631
 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):  9.27E-008 Pa (6.95E-010 mm Hg)
  Log Koa (Koawin est  ): 16.436
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  32.4 
       Octanol/air (Koa) model:  6.7E+003 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.999 
       Mackay model           :  1 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 332.2243 E-12 cm3/molecule-sec
      Half-Life =     0.032 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    23.180 Min
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    64.055000 E-17 cm3/molecule-sec
      Half-Life =     0.018 Days (at 7E11 mol/cm3)
      Half-Life =     25.763 Min
   Fraction sorbed to airborne particulates (phi): 0.999 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  2010
      Log Koc:  3.303 

 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 = 0.301 (BCF = 2)
       log Kow used: 1.30 (expkow database)

 Volatilization from Water:
    Henry LC:  1.79E-017 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 6.537E+013  hours   (2.724E+012 days)
    Half-Life from Model Lake : 7.131E+014  hours   (2.971E+013 days)

 Removal In Wastewater Treatment:
    Total removal:               1.93  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.83  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       3.59e-008       0.276        1000       
   Water     38.7            1.44e+003    1000       
   Soil      61.3            2.88e+003    1000       
   Sediment  0.0903          1.3e+004     0          
     Persistence Time: 1.39e+003 hr

Click to predict properties on the Chemicalize site


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