ChemSpider 2D Image | Oxytetracycline | C22H24N2O9

Oxytetracycline

  • Molecular FormulaC22H24N2O9
  • Average mass460.434 Da
  • Monoisotopic mass460.148193 Da
  • ChemSpider ID10482174

  • defined stereocentres - 6 of 6 defined stereocentres

More details:

Featured data source
The Merck Index Online

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

(4S,4aR,5S,5aR,6S,12aS)-4-(Dimethylamino)-3,5,6,10,12,12a-hexahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydro-2-tetracencarboxamid [German] [ACD/IUPAC Name]
(4S,4aR,5S,5aR,6S,12aS)-4-(Dimethylamino)-3,5,6,10,12,12a-hexahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydro-2-tetracenecarboxamide [ACD/IUPAC Name]
(4S,4aR,5S,5aR,6S,12aS)-4-(Diméthylamino)-3,5,6,10,12,12a-hexahydroxy-6-méthyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydro-2-tétracènecarboxamide [French] [ACD/IUPAC Name]
(4S,4aR,5S,5aR,6S,12aS)-4-(Dimethylamino)-3,5,6,10,12,12a-hexahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracen-2-carboxamid
(4S,4aR,5S,5aR,6S,12aS)-4-(Dimethylamino)-3,5,6,10,12,12a-hexahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide
[4S-(4a,4aa,5a,5aa,6b,12aa)]-4-(Dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,6,10,12,12a-hexahydroxy-6-methyl-1,11-dioxo-2-naphthacenecarboxamide
15251-48-6 [RN]
201-212-8 [EINECS]
2-Naphthacenecarboxamide, 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,6,10,12,12a-hexahydroxy-6-methyl-1,11-dioxo-, (4S,4aR,5S,5aR,6S,12aS)- [ACD/Index Name]
7179-50-2 [RN]
More...

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

103 [DBID]
2686362 [DBID]
2686362; 2714587 [DBID]
2714587 [DBID]
BRN 2714587 [DBID]
HSDB 3145 [DBID]
LA 200 [DBID]
NCI-C56473 [DBID]
NSC 9169 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Toxicity:

      Organic Compound; Drug; Food Toxin; Metabolite; Synthetic Compound; Tetracycline Toxin, Toxin-Target Database T3D3953

    • Safety:

      D06AA03 Wikidata Q411646
      G01AA07 Wikidata Q411646
      J01AA06 Wikidata Q411646
      S01AA04 Wikidata Q411646

    • Chemical Class:

      A tetracycline used for treatment of infections caused by a variety of Gram positive and Gram negative microorganisms including <ital>Mycoplasma pneumoniae</ital>, <ital>Pasteurella pestis</ital>, <it al>Escherichia coli</ital>, <ital>Haemophilus influenzae</ital> (respiratory infections), and <ital>Diplococcus pneumoniae</ital>. ChEBI CHEBI:133011, CHEBI:27701
      A tetracycline used for treatment of infections caused by a variety of Gram positive and Gram negative microorganisms including Mycoplasma pneumoniae, Pasteurella pestis, Escherichia coli, Haemophilus influenzae (respiratory infections), and Diplococcus pneumoniae. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:27701, CHEBI:27701
      A zwitterion obtained by transfer of a proton from the 2-hydroxy group to the adjacent tertiary amino group of oxytetracycline; major species at pH 7.3. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:133011, CHEBI:133011, CHEBI:27701

    • Bio Activity:

      Antibacterial MedChem Express HY-B0275
      Anti-infection MedChem Express HY-B0275
      Anti-infection; MedChem Express HY-B0275
      Oxytetracycline is a tetracycline analog isolated from the actinomycete streptomyces rimosus and used in a wide variety of clinical conditions.; Target: Antibacterial; Oxytetracycline was the second of the broad-spectrum tetracycline group of antibiotics to be discovered. MedChem Express HY-B0275
      Oxytetracycline is a tetracycline analog isolated from the actinomycete streptomyces rimosus and used in a wide variety of clinical conditions.;Target: AntibacterialOxytetracycline was the second of the broad-spectrum tetracycline group of antibiotics to be discovered. Oxytetracycline works by interfering with the ability of bacteria to produce essential proteins. Without these proteins, the bacteria cannot grow, multiply and increase in numbers. Oxytetracycline therefore stops the spread of the infection and the remaining bacteria are killed by the immune system or eventually die.Oxytetracycline is a broad-spectrum antibiotic, active against a wide variety of bacteria. However, some strains of bacteria have developed resistance to this antibiotic, which has reduced its effectiveness for treating some types of infections [1, 2]. MedChem Express HY-B0275

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

Density: 1.7±0.1 g/cm3
Boiling Point: 839.6±65.0 °C at 760 mmHg
Vapour Pressure: 0.0±3.3 mmHg at 25°C
Enthalpy of Vaporization: 127.9±3.0 kJ/mol
Flash Point: 461.6±34.3 °C
Index of Refraction: 1.762
Molar Refractivity: 110.6±0.4 cm3
#H bond acceptors: 11
#H bond donors: 8
#Freely Rotating Bonds: 2
#Rule of 5 Violations: 2
ACD/LogP: -1.50
ACD/LogD (pH 5.5): -3.85
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -4.25
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 202 Å2
Polarizability: 43.8±0.5 10-24cm3
Surface Tension: 111.3±5.0 dyne/cm
Molar Volume: 268.2±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) =  -2.87
    Log Kow (Exper. database match) =  -0.90
       Exper. Ref:  Sangster (1994)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  781.66  (Adapted Stein & Brown method)
    Melting Pt (deg C):  344.17  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  9.05E-023  (Modified Grain method)
    MP  (exp database):  184.5 deg C
    Subcooled liquid VP: 4.19E-021 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):  1399
       log Kow used: -0.90 (expkow database)
       no-melting pt equation used
     Water Sol (Exper. database match) =  313 mg/L (25 deg C)
        Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1e+006 mg/L
    Wat Sol (Exper. database match) =  313.00
       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 :   1.70E-025  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  3.919E-026 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -0.90  (exp database)
  Log Kaw used:  -23.158  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  22.258
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.7710
   Biowin2 (Non-Linear Model)     :   0.0410
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.9397  (months      )
   Biowin4 (Primary Survey Model) :   3.1776  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.3781
   Biowin6 (MITI Non-Linear Model):   0.0077
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -2.1471
 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):  5.59E-019 Pa (4.19E-021 mm Hg)
  Log Koa (Koawin est  ): 22.258
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  5.37E+012 
       Octanol/air (Koa) model:  4.45E+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 = 264.9478 E-12 cm3/molecule-sec
      Half-Life =     0.040 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    29.067 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    :  97.2
      Log Koc:  1.988 

 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: -0.90 (expkow database)

 Volatilization from Water:
    Henry LC:  1.7E-025 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River:  7.39E+021  hours   (3.079E+020 days)
    Half-Life from Model Lake : 8.062E+022  hours   (3.359E+021 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       1.37e-005       0.897        1000       
   Water     49.4            1.44e+003    1000       
   Soil      50.5            2.88e+003    1000       
   Sediment  0.0961          1.3e+004     0          
     Persistence Time: 1.17e+003 hr

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