ChemSpider 2D Image | Demeclocycline | C21H21ClN2O8

Demeclocycline

  • Molecular FormulaC21H21ClN2O8
  • Average mass464.853 Da
  • Monoisotopic mass464.098633 Da
  • ChemSpider ID10482117

  • defined stereocentres - 5 of 5 defined stereocentres

More details:

Featured data source
The Merck Index Online

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

(4S-(4a,4aa,5aa,6b,12aa))-7-Chloro-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-1,11-dioxo-2-naphthacenecarboxamide
(4S,4aS,5aS,6S,12aS)-7-Chlor-4-(dimethylamino)-3,6,10,12,12a-pentahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydro-2-tetracencarboxamid [German] [ACD/IUPAC Name]
(4S,4aS,5aS,6S,12aS)-7-Chloro-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-1,11-dioxo-2-naphthacenecarboxamide
(4S,4aS,5aS,6S,12aS)-7-Chloro-4-(dimethylamino)-3,6,10,12,12a-pentahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydro-2-tetracenecarboxamide [ACD/IUPAC Name]
(4S,4aS,5aS,6S,12aS)-7-Chloro-4-(diméthylamino)-3,6,10,12,12a-pentahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydro-2-tétracènecarboxamide [French] [ACD/IUPAC Name]
(4S,4aS,5aS,6S,12aS)-7-Chloro-4-(dimethylamino)-3,6,10,12,12a-pentahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide
200-592-2 [EINECS]
204-834-8 [EINECS]
2-Naphthacenecarboxamide, 7-chloro-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-1,11-dioxo-, (4S,4aS,5aS,6S,12aS)- [ACD/Index Name]
5R5W9ICI6O
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

917 [DBID]
2230579 [DBID]
HSDB 3051 [DBID]
RP 10192 [DBID]
  • Miscellaneous

    • Toxicity:

      Organic Compound; Drug; Anti-Bacterial Agent; Metabolite; Synthetic Compound; Tetracycline Toxin, Toxin-Target Database T3D3951

    • Safety:

      D06AA01 Wikidata Q2736402
      J01AA01 Wikidata Q2736402

    • Chemical Class:

      Tetracycline which lacks the methyl substituent at position 7 and in which the hydrogen <ital>para</ital>- to the phenolic hydroxy group is substituted by chlorine. Like tetracycline, it is an antibio tic, but being excreted more slowly, effective blood levels are maintained for longer. It is used (mainly as the hydrochloride) for the treatment of Lyme disease, acne and bronchitis, as well as for h yponatraemia (low blood sodium concentration) due to the syndrome of inappropriate antidiuretic hormone (SIADH) where fluid restriction alone has been ineffective. ChEBI CHEBI:4392
      Tetracycline which lacks the methyl substituent at position 7 and in which the hydrogen para- to the phenolic hydroxy group is substituted by chlorine. Like tetracycline, it is an antibio; tic, but be ing excreted more slowly, effective blood levels are maintained for longer. It is used (mainly as the hydrochloride) for the treatment of Lyme disease, acne and bronchitis, as well as for hyponatraemi a (low blood sodium concentration) due to the syndrome of inappropriate antidiuretic hormone (SIADH) where fluid restriction alone has been ineffective. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:4392
      Tetracycline which lacks the methyl substituent at position 7 and in which the hydrogen para- to the phenolic hydroxy group is substituted by chlorine. Like tetracycline, it is an antibiotic, but bein g excreted more slowly, effective blood levels are maintained for longer. It is used (mainly as the hydrochloride) for the treatment of Lyme disease, acne and bronchitis, as well as for hyponatraemia (low blood sodium concentration) due to the syndrome of inappropriate antidiuretic hormone (SIADH) where fluid restriction alone has been ineffective. ChEBI CHEBI:4392

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

Density: 1.8±0.1 g/cm3
Boiling Point: 787.1±60.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.9 mmHg at 25°C
Enthalpy of Vaporization: 120.1±3.0 kJ/mol
Flash Point: 429.8±32.9 °C
Index of Refraction: 1.761
Molar Refractivity: 109.3±0.4 cm3
#H bond acceptors: 10
#H bond donors: 7
#Freely Rotating Bonds: 2
#Rule of 5 Violations: 2
ACD/LogP: -1.07
ACD/LogD (pH 5.5): -2.97
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -3.40
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 182 Å2
Polarizability: 43.3±0.5 10-24cm3
Surface Tension: 108.0±5.0 dyne/cm
Molar Volume: 265.2±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) =  -1.14

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  763.95  (Adapted Stein & Brown method)
    Melting Pt (deg C):  335.90  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  5.25E-024  (Modified Grain method)
    Subcooled liquid VP: 1.78E-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):  2092
       log Kow used: -1.14 (estimated)
       no-melting pt equation used
     Water Sol (Exper. database match) =  1520 mg/L (21 deg C)
        Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  85767 mg/L
    Wat Sol (Exper. database match) =  1520.00
       Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.60E-024  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.535E-027 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -1.14  (KowWin est)
  Log Kaw used:  -21.973  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  20.833
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.7704
   Biowin2 (Non-Linear Model)     :   0.0291
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.9355  (months      )
   Biowin4 (Primary Survey Model) :   3.1593  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.2924
   Biowin6 (MITI Non-Linear Model):   0.0060
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -2.1665
 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):  2.37E-018 Pa (1.78E-020 mm Hg)
  Log Koa (Koawin est  ): 20.833
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  1.26E+012 
       Octanol/air (Koa) model:  1.67E+008 
   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 = 211.7622 E-12 cm3/molecule-sec
      Half-Life =     0.051 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.606 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
   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    :  63.31
      Log Koc:  1.801 

 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: -1.14 (estimated)

 Volatilization from Water:
    Henry LC:  2.6E-024 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 4.855E+020  hours   (2.023E+019 days)
    Half-Life from Model Lake : 5.297E+021  hours   (2.207E+020 days)

 Removal In Wastewater Treatment:
    Total removal:               1.85  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.75  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       0.00411         1.1          1000       
   Water     49.8            1.44e+003    1000       
   Soil      50.1            2.88e+003    1000       
   Sediment  0.0969          1.3e+004     0          
     Persistence Time: 1.13e+003 hr

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