ChemSpider 2D Image | fosmidomycin | C4H10NO5P

fosmidomycin

  • Molecular FormulaC4H10NO5P
  • Average mass183.100 Da
  • Monoisotopic mass183.029663 Da
  • ChemSpider ID555

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(3-(Formyl(hydroxy)amino)propyl)phosphonic Acid
{3-[Formyl(hydroxy)amino]propyl}phosphonic acid [ACD/IUPAC Name]
{3-[Formyl(hydroxy)amino]propyl}phosphonsäure [German] [ACD/IUPAC Name]
66508-53-0 [RN]
Acide {3-[formyl(hydroxy)amino]propyl}phosphonique [French] [ACD/IUPAC Name]
fosmidomycin [INN] [Wiki]
Fosmidomycina [Spanish] [INN]
Fosmidomycine [French] [INN]
fosmidomycinum [Latin] [INN]
Phosphonic acid, [3-(formylhydroxyamino)propyl]- [ACD/Index Name]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

5104 [DBID]
5829E3D9I9 [DBID]
AIDS091712 [DBID]
AIDS-091712 [DBID]
Antibiotic FR 31564 [DBID]
CHEMBL203125 [DBID]
DXA [DBID]
FR 31564 [DBID]
FR-31564 [DBID]
NChemBio.2007.9-comp4 [DBID]
More...
  • Miscellaneous
    • Chemical Class:

      Propylphosphonic acid in which one of the hydrogens at position 3 is substituted by a formyl(hydroxy)amino group. An antibiotic obtained from <ital>Streptomyces lavendulae</ital>, it specifically inhi bits DXP reductoisomerase (EC 1.1.1.267), a key enzyme in the non-mevalonate pathway of isoprenoid biosynthesis. ChEBI CHEBI:443725
      Propylphosphonic acid in which one of the hydrogens at position 3 is substituted by a formyl(hydroxy)amino group. An antibiotic obtained from Streptomyces lavendulae, it specifically inhi; bits DXP re ductoisomerase (EC 1.1.1.267), a key enzyme in the non-mevalonate pathway of isoprenoid biosynthesis. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:443725

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module

Density: 1.6±0.1 g/cm3
Boiling Point: 463.7±55.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.5 mmHg at 25°C
Enthalpy of Vaporization: 79.4±6.0 kJ/mol
Flash Point: 234.3±31.5 °C
Index of Refraction: 1.533
Molar Refractivity: 36.0±0.3 cm3
#H bond acceptors: 6
#H bond donors: 3
#Freely Rotating Bonds: 4
#Rule of 5 Violations: 0
ACD/LogP: -2.47
ACD/LogD (pH 5.5): -5.30
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -6.01
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 108 Å2
Polarizability: 14.3±0.5 10-24cm3
Surface Tension: 81.7±3.0 dyne/cm
Molar Volume: 115.8±3.0 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) =  -2.07

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  411.82  (Adapted Stein & Brown method)
    Melting Pt (deg C):  83.63  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  3.81E-009  (Modified Grain method)
    Subcooled liquid VP: 1.39E-008 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):  1e+006
       log Kow used: -2.07 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1e+006 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Neutral Organics-acid

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.96E-020  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  9.179E-016 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -2.07  (KowWin est)
  Log Kaw used:  -18.096  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  16.026
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.6604
   Biowin2 (Non-Linear Model)     :   0.6008
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.7945  (weeks       )
   Biowin4 (Primary Survey Model) :   3.5836  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.3157
   Biowin6 (MITI Non-Linear Model):   0.1867
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.9141
 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):  1.85E-006 Pa (1.39E-008 mm Hg)
  Log Koa (Koawin est  ): 16.026
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  1.62 
       Octanol/air (Koa) model:  2.61E+003 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.983 
       Mackay model           :  0.992 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  28.5259 E-12 cm3/molecule-sec
      Half-Life =     0.375 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     4.499 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.988 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  36.3
      Log Koc:  1.560 

 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: -2.07 (estimated)

 Volatilization from Water:
    Henry LC:  1.96E-020 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 4.042E+016  hours   (1.684E+015 days)
    Half-Life from Model Lake :  4.41E+017  hours   (1.837E+016 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       2.92e-011       9            1000       
   Water     39              360          1000       
   Soil      60.9            720          1000       
   Sediment  0.0713          3.24e+003    0          
     Persistence Time: 579 hr




                    

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