ChemSpider 2D Image | Anisomycin | C14H19NO4

Anisomycin

  • Molecular FormulaC14H19NO4
  • Average mass265.305 Da
  • Monoisotopic mass265.131409 Da
  • ChemSpider ID222267

  • defined stereocentres - 3 of 3 defined stereocentres

More details:

Featured data source
The Merck Index Online

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

(-)-Anisomycin
(2R,3S,4S)-2-(4-Methoxybenzyl)-3,4-pyrrolidinediol-3-acetate
(2R,3S,4S)-4-Hydroxy-2-(4-methoxybenzyl)-3-pyrrolidinyl acetate [ACD/IUPAC Name]
(2R,3S,4S)-4-Hydroxy-2-(4-methoxybenzyl)-3-pyrrolidinyl-acetat [German] [ACD/IUPAC Name]
(2R,3S,4S)-4-Hydroxy-2-(4-methoxybenzyl)pyrrolidin-3-yl acetate
(2R,3S,4S)-4-hydroxy-2-[(4-methoxyphenyl)methyl]pyrrolidin-3-yl acetate
1,4,5-Trideoxy-1,4-imino-5-(4-methoxyphenyl)-D-xylo-pentitol 3-Acetate
2-[(4-Methoxyphenyl)methyl]-3,4-pyrrolidinediol 3-acetate
245-269-7 [EINECS]
3,4-Pyrrolidinediol, 2-[(4-methoxyphenyl)methyl]-, 3-acetate, (2R,3S,4S)- [ACD/Index Name]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

20705 [DBID]
6C74YM2NGI [DBID]
A9789_SIGMA [DBID]
AIDS031977 [DBID]
AIDS-031977 [DBID]
Bio1_000350 [DBID]
Bio1_000839 [DBID]
Bio1_001328 [DBID]
CBiol_002064 [DBID]
DivK1c_000855 [DBID]
More...
  • Experimental Physico-chemical Properties

    • Experimental Solubility:

      10 mM in DMSO MedChem Express HY-18982
      DMSO 50 mg/mL; Water 5 mg/mL MedChem Express HY-18982
      Soluble in ethanol (50 mM) and DMSO (100 mM) Hello Bio HB2239
      Soluble to 100 mM in ethanol and to 100 mM in DMSO Tocris Bioscience 1290
      Soluble to 50 mM in ethanol and to 100 mM in DMSO Tocris Bioscience 1290
  • Miscellaneous

    • Chemical Class:

      An antibiotic isolated from various <ital>Streptomyces</ital> species. It interferes with protein and DNA synthesis by inhibiting peptidyl transferase or the 80S ribosome system. ChEBI CHEBI:338412
      An antibiotic isolated from various Streptomyces species. It interferes with protein and DNA synthesis by inhibiting peptidyl transferase or the 80S ribosome system. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:338412, CHEBI:338412

    • Bio Activity:

      <p>Protein synthesis inhibitor which prevents elongation and causes polysome stabilization by binding to the 60S ribosomal subunit to prevent peptide bond formation.</p> <p>Also acts as a potent JNK and p38 MAPK activator.</p> <p><br />Initiates intracellular signals for rapid induction of immediate-early (IE) genes (e.g. c-fos, fosB, c-jun, JunB and JunD).</p> <p><br />Additionally, thought to block late long-term potentiation (L-LTP) and at high doses reduces neuronal activity.</p> Hello Bio HB2239
      Anisomycin is a pyrrolidine antibiotic, acts as an anti-fungal antibiotic which inhibits Protein Synthesis, also is a potent activator of SAPKs/JNKs.; Target: antibiotic; in vitro: Anisomycin inhibits EAC cell proliferation in concentration-dependent manner. MedChem Express HY-18982
      Antibacterial MedChem Express HY-18982
      Antibacterial JNK MedChem Express HY-18982
      Antibiotics Hello Bio HB2239
      Anti-infection MedChem Express HY-18982
      Anti-infection; MAPK; MedChem Express HY-18982
      Enzymes Tocris Bioscience 1290
      JNK, SAPK and p38 activator Tocris Bioscience 1290
      Kinases Tocris Bioscience 1290
      MAPK Family Tocris Bioscience 1290
      Protein synthesis inhibitor (blocks translation). Potent activator of stress-activated protein kinases (JNK/SAPK) and p38 MAP kinase. Acts as a potent signaling agonist to selectively elicit homologou s desensitization of immediate early gene induction (c-fos, fosB, c-jun, junB and junD). Tocris Bioscience 1290
      Protein synthesis inhibitor (blocks translation). Potent activator of stress-activated protein kinases (JNK/SAPK) and p38 MAP kinase. Acts as a potent signaling agonist to selectively elicit homologous desensitization of immediate early gene induction (c-fos, fosB, c-jun, junB and junD). Tocris Bioscience 1290
      Protein synthesis inhibitor. Potent JNK / p38 MAPK activator. Hello Bio HB2239

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

Density: 1.2±0.1 g/cm3
Boiling Point: 398.7±42.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.0 mmHg at 25°C
Enthalpy of Vaporization: 68.5±3.0 kJ/mol
Flash Point: 194.9±27.9 °C
Index of Refraction: 1.558
Molar Refractivity: 70.5±0.4 cm3
#H bond acceptors: 5
#H bond donors: 2
#Freely Rotating Bonds: 5
#Rule of 5 Violations: 0
ACD/LogP: 0.42
ACD/LogD (pH 5.5): -1.88
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -0.32
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 4.21
Polar Surface Area: 68 Å2
Polarizability: 27.9±0.5 10-24cm3
Surface Tension: 48.8±5.0 dyne/cm
Molar Volume: 218.7±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) =  0.61

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  384.94  (Adapted Stein & Brown method)
    Melting Pt (deg C):  144.87  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  3.48E-008  (Modified Grain method)
    MP  (exp database):  140.5 deg C
    Subcooled liquid VP: 5.1E-007 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):  5.965e+004
       log Kow used: 0.61 (estimated)
       no-melting pt equation used
     Water Sol (Exper. database match) =  6550 mg/L (28 deg C)
        Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1.1109e+005 mg/L
    Wat Sol (Exper. database match) =  6550.00
       Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Aliphatic Amines
       Esters

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   7.13E-015  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  2.037E-013 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  0.61  (KowWin est)
  Log Kaw used:  -12.535  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  13.145
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.2946
   Biowin2 (Non-Linear Model)     :   0.9998
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.8045  (weeks       )
   Biowin4 (Primary Survey Model) :   3.8752  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.6913
   Biowin6 (MITI Non-Linear Model):   0.4008
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.8317
 Ready Biodegradability Prediction:   YES

Hydrocarbon Biodegradation (BioHCwin v1.01):
    Structure incompatible with current estimation method!

 Sorption to aerosols (25 Dec C)[AEROWIN v1.00]:
  Vapor pressure (liquid/subcooled):  6.8E-005 Pa (5.1E-007 mm Hg)
  Log Koa (Koawin est  ): 13.145
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.0441 
       Octanol/air (Koa) model:  3.43 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.614 
       Mackay model           :  0.779 
       Octanol/air (Koa) model:  0.996 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 125.2463 E-12 cm3/molecule-sec
      Half-Life =     0.085 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.025 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.697 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  55.02
      Log Koc:  1.741 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
  Total Kb for pH > 8 at 25 deg C :  2.805E-003  L/mol-sec
  Kb Half-Life at pH 8:       7.829  years  
  Kb Half-Life at pH 7:      78.287  years  

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 0.500 (BCF = 3.162)
       log Kow used: 0.61 (estimated)

 Volatilization from Water:
    Henry LC:  7.13E-015 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.338E+011  hours   (5.573E+009 days)
    Half-Life from Model Lake : 1.459E+012  hours   (6.08E+010 days)

 Removal In Wastewater Treatment:
    Total removal:               1.86  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.77  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       4.41e-007       2.05         1000       
   Water     37              360          1000       
   Soil      63              720          1000       
   Sediment  0.0702          3.24e+003    0          
     Persistence Time: 593 hr

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