ChemSpider 2D Image | doxycycline (anhydrous) | C22H24N2O8

doxycycline (anhydrous)

  • Molecular FormulaC22H24N2O8
  • Average mass444.435 Da
  • Monoisotopic mass444.153259 Da
  • ChemSpider ID10469369

  • defined stereocentres - 6 of 6 defined stereocentres

More details:

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

doxycycline (anhydrous)
(4S,4aR,5S,5aR,6R,12aS)-4-(Dimethylamino)-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydro-2-tetracencarboxamid [German] [ACD/IUPAC Name]
(4S,4aR,5S,5aR,6R,12aS)-4-(Dimethylamino)-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydro-2-tetracenecarboxamide [ACD/IUPAC Name]
(4S,4aR,5S,5aR,6R,12aS)-4-(Diméthylamino)-3,5,10,12,12a-pentahydroxy-6-méthyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydro-2-tétracènecarboxamide [French] [ACD/IUPAC Name]
(4S,4aR,5S,5aR,6R,12aS)-4-(dimethylamino)-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide
2-Naphthacenecarboxamide, 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-, (4S,4aR,5S,5aR,6R,12aS)- [ACD/Index Name]
doxiciclina [Italian]
Doxycycline [INN] [Wiki]
Doxycycline anhydrous
doxycyclinum [Latin] [INN]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

2125 [DBID]
334895S862 [DBID]
CCRIS 937 [DBID]
UNII:334895S862 [DBID]
UNII-334895S862 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Toxicity:

      Organic Compound; Drug; Antimalarial; Anti-Bacterial Agent; Metabolite; Synthetic Compound; Tetracycline Toxin, Toxin-Target Database T3D3950

    • Safety:

      A01AB22 Wikidata Q422442
      J01AA02 Wikidata Q422442

    • Chemical Class:

      Tetracycline in which the 5<stereo>beta</stereo>-hydrogen is replaced by a hydroxy group, while the 6<stereo>alpha</stereo>-hydroxy group is replaced by hydrogen. A semi-synthetic tetracycline antibio tic, it is used to inhibit bacterial protein synthesis and treat non-gonococcal urethritis and cervicitis, exacerbations of bronchitis in patients with chronic obstructive pulmonary disease (COPD), an d adult periodontitis. ChEBI CHEBI:50845
      Tetracycline in which the 5beta-hydrogen is replaced by a hydroxy group, while the 6alpha-hydroxy group is replaced by hydrogen. A semi-synthetic tetracycline antibio; tic, it is used to inhibit bacte rial protein synthesis and treat non-gonococcal urethritis and cervicitis, exacerbations of bronchitis in patients with chronic obstructive pulmonary disease (COPD), and adult periodontitis. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:50845
      Tetracycline in which the 5beta-hydrogen is replaced by a hydroxy group, while the 6alpha-hydroxy group is replaced by hydrogen. A semi-synthetic tetracycline antibiotic, it is used to inhibit bacteri al protein synthesis and treat non-gonococcal urethritis and cervicitis, exacerbations of bronchitis in patients with chronic obstructive pulmonary disease (COPD), and adult periodontitis. ChEBI CHEBI:50845

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

Density: 1.6±0.1 g/cm3
Boiling Point: 762.6±60.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.7 mmHg at 25°C
Enthalpy of Vaporization: 116.5±3.0 kJ/mol
Flash Point: 415.0±32.9 °C
Index of Refraction: 1.737
Molar Refractivity: 109.0±0.4 cm3
#H bond acceptors: 10
#H bond donors: 7
#Freely Rotating Bonds: 2
#Rule of 5 Violations: 2
ACD/LogP: -0.54
ACD/LogD (pH 5.5): -2.98
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -3.29
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 182 Å2
Polarizability: 43.2±0.5 10-24cm3
Surface Tension: 99.2±5.0 dyne/cm
Molar Volume: 271.1±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) =  -1.36
    Log Kow (Exper. database match) =  -0.02
       Exper. Ref:  Sangster (1994)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  753.50  (Adapted Stein & Brown method)
    Melting Pt (deg C):  331.01  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.42E-023  (Modified Grain method)
    Subcooled liquid VP: 4.16E-020 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):  312.9
       log Kow used: -0.02 (expkow database)
       no-melting pt equation used
     Water Sol (Exper. database match) =  630 mg/L (25 deg C)
        Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1.2211e+005 mg/L
    Wat Sol (Exper. database match) =  630.00
       Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   4.66E-024  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  2.654E-026 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -0.02  (exp database)
  Log Kaw used:  -21.720  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  21.700
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.0172
   Biowin2 (Non-Linear Model)     :   0.3488
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.1124  (months      )
   Biowin4 (Primary Survey Model) :   3.2856  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.3484
   Biowin6 (MITI Non-Linear Model):   0.0107
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.8942
 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):  5.55E-018 Pa (4.16E-020 mm Hg)
  Log Koa (Koawin est  ): 21.700
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  5.41E+011 
       Octanol/air (Koa) model:  1.23E+009 
   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 = 265.8565 E-12 cm3/molecule-sec
      Half-Life =     0.040 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    28.967 Min
   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
   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    :  64.63
      Log Koc:  1.810 

 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: -0.02 (expkow database)

 Volatilization from Water:
    Henry LC:  4.66E-024 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 2.649E+020  hours   (1.104E+019 days)
    Half-Life from Model Lake :  2.89E+021  hours   (1.204E+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       0.00303         0.894        1000       
   Water     49.2            1.44e+003    1000       
   Soil      50.7            2.88e+003    1000       
   Sediment  0.0964          1.3e+004     0          
     Persistence Time: 1.14e+003 hr

Click to predict properties on the Chemicalize site


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