ChemSpider 2D Image | Methacycline | C22H22N2O8

Methacycline

  • Molecular FormulaC22H22N2O8
  • Average mass442.419 Da
  • Monoisotopic mass442.137604 Da
  • ChemSpider ID4444513

  • Double-bond stereo - Double-bond stereo

    defined stereocentres - 5 of 5 defined stereocentres

More details:

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

Methacycline
(2Z,4S,4aR,5S,5aR,12aS)-2-[Amino(hydroxy)methylen]-4-(dimethylamino)-5,10,11,12a-tetrahydroxy-6-methylen-4a,5a,6,12a-tetrahydro-1,3,12(2H,4H,5H)-tetracentrion [German] [ACD/IUPAC Name]
(2Z,4S,4aR,5S,5aR,12aS)-2-[Amino(hydroxy)methylene]-4-(dimethylamino)-5,10,11,12a-tetrahydroxy-6-methylene-4a,5a,6,12a-tetrahydro-1,3,12(2H,4H,5H)-tetracenetrione [ACD/IUPAC Name]
(2Z,4S,4aR,5S,5aR,12aS)-2-[Amino(hydroxy)méthylène]-4-(diméthylamino)-5,10,11,12a-tétrahydroxy-6-méthylène-4a,5a,6,12a-tétrahydro-1,3,12(2H,4H,5H)-tétracènetrione [French] [ACD/IUPAC Name]
1,3,12(2H,4H,5H)-Naphthacenetrione, 2-(aminohydroxymethylene)-4-(dimethylamino)-4a,5a,6,12a-tetrahydro-5,10,11,12a-tetrahydroxy-6-methylene-, (2Z,4S,4aR,5S,5aR,12aS)- [ACD/Index Name]
914-00-1 [RN]
Metacycline [INN]
Methacyclin
(2Z,4S,4AR,5S,5AR,12AS)-2-[AMINO(HYDROXY)METHYLIDENE]-4-(DIMETHYLAMINO)-5,10,11,12A-TETRAHYDROXY-6-METHYLIDENE-1,2,3,4,4A,5,5A,6,12,12A-DECAHYDROTETRACENE-1,3,12-TRIONE
2-Naphthacenecarboxamide, 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methylene-1,11-dioxo-, (4S-(4α,4aα,5α,5aα,12aα))-
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

C07654 [DBID]
GS 2876 [DBID]
GS-2876 [DBID]
HSDB 3118 [DBID]

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

Density: 1.7±0.1 g/cm3
Boiling Point: 695.1±55.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.3 mmHg at 25°C
Enthalpy of Vaporization: 106.9±3.0 kJ/mol
Flash Point: 374.2±31.5 °C
Index of Refraction: 1.753
Molar Refractivity: 108.6±0.4 cm3
#H bond acceptors: 10
#H bond donors: 7
#Freely Rotating Bonds: 1
#Rule of 5 Violations: 2
ACD/LogP: 1.21
ACD/LogD (pH 5.5): -0.74
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 2.50
ACD/LogD (pH 7.4): -2.37
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 182 Å2
Polarizability: 43.1±0.5 10-24cm3
Surface Tension: 101.5±5.0 dyne/cm
Molar Volume: 265.6±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) =  -0.22

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  716.48  (Adapted Stein & Brown method)
    Melting Pt (deg C):  313.72  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  4.74E-022  (Modified Grain method)
    Subcooled liquid VP: 8.31E-019 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):  9831
       log Kow used: -0.22 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  14558 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Aliphatic Amines
       Phenols
       Vinyl/Allyl Ketones
       Vinyl/Allyl Alcohols

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   5.35E-026  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  2.807E-026 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -0.22  (KowWin est)
  Log Kaw used:  -23.660  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  23.440
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.9140
   Biowin2 (Non-Linear Model)     :   0.0389
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.2478  (months      )
   Biowin4 (Primary Survey Model) :   3.1726  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.4005
   Biowin6 (MITI Non-Linear Model):   0.0065
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.5270
 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):  1.11E-016 Pa (8.31E-019 mm Hg)
  Log Koa (Koawin est  ): 23.440
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  2.71E+010 
       Octanol/air (Koa) model:  6.76E+010 
   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 = 389.1440 E-12 cm3/molecule-sec
      Half-Life =     0.027 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    19.790 Min
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    27.474998 E-17 cm3/molecule-sec
      Half-Life =     0.042 Days (at 7E11 mol/cm3)
      Half-Life =      1.001 Hrs
   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    :  314.4
      Log Koc:  2.497 

 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: -0.22 (estimated)

 Volatilization from Water:
    Henry LC:  5.35E-026 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 2.302E+022  hours   (9.591E+020 days)
    Half-Life from Model Lake : 2.511E+023  hours   (1.046E+022 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       1.64e-006       0.398        1000       
   Water     49.1            1.44e+003    1000       
   Soil      50.8            2.88e+003    1000       
   Sediment  0.0959          1.3e+004     0          
     Persistence Time: 1.18e+003 hr

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