ChemSpider 2D Image | miglustat | C10H21NO4

miglustat

  • Molecular FormulaC10H21NO4
  • Average mass219.278 Da
  • Monoisotopic mass219.147064 Da
  • ChemSpider ID46764
  • defined stereocentres - 4 of 4 defined stereocentres


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Featured data source



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

(2R,3R,4R,5S)-1-Butyl-2-(hydroxymethyl)-3,4,5-piperidinetriol [ACD/IUPAC Name]
(2R,3R,4R,5S)-1-Butyl-2-(hydroxyméthyl)-3,4,5-pipéridinetriol [French] [ACD/IUPAC Name]
(2R,3R,4R,5S)-1-Butyl-2-(hydroxymethyl)-3,4,5-piperidintriol [German] [ACD/IUPAC Name]
(2R,3R,4R,5S)-1-Butyl-2-(hydroxymethyl)piperidine-3,4,5-triol
1,5-(BUTYLIMINO)-1,5-DIDEOXY-D-GLUCITOL
3,4,5-Piperidinetriol, 1-butyl-2-(hydroxymethyl)-, (2R,3R,4R,5S)- [ACD/Index Name]
72599-27-0 [RN]
8138
ADN3S497AZ
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

AIDS000261 [DBID]
AIDS-000261 [DBID]
nchembio.81-comp12 [DBID]
nchembio850-comp5 [DBID]
OGT 918 [DBID]
OGT-918 [DBID]
SC 48334 [DBID]
SC-48334 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      A16AX06 Wikidata Q425911
    • Chemical Class:

      A hydroxypiperidine that is deoxynojirimycin in which the amino hydrogen is replaced by a butyl group. ChEBI CHEBI:50381
    • Bio Activity:

      Miglustat(OGT918) is an inhibitor of glucosylceramide synthase, primarily to treat Type I Gaucher disease (GD1). MedChem Express
      Miglustat(OGT918) is an inhibitor of glucosylceramide synthase, primarily to treat Type I Gaucher disease (GD1).; Target: Others; Miglustat is an inhibitor of the ceramide-specific glycosyltransferase, which catalyzes the first step of glycosphingolipid biosynthesis and is currently approved for the oral treatment of type 1 GD [1]. MedChem Express HY-17020
      Miglustat(OGT918) is an inhibitor of glucosylceramide synthase, primarily to treat Type I Gaucher disease (GD1).;Target: Miglustat is an inhibitor of the ceramide-specific glycosyltransferase, which catalyzes the first step of glycosphingolipid biosynthesis and is currently approved for the oral treatment of type 1 GD [1]. Consumption of a standard high-fat breakfast within 30 minutes before administration of miglustat significantly reduced peak exposure but did not significantly affect the extent of systemic exposure to miglustat. The peak plasma concentration (C(max)) decreased by 36% on average following administration with food. Area under the plasma concentration-time curve (AUC(0-infinity)) showed a modest (14%) decrease with food, but the 90% confidence interval was within the acceptance limit of 80% to 125%. The median (min-max) time to C(max) (t(max)) was prolonged from 2.5 (1.0-4.0) hours in the fasted state to 4.5 (1.5-8.0) hours in the fed state, whereas the appar MedChem Express HY-17020
      Others MedChem Express HY-17020

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

Density: 1.2±0.1 g/cm3
Boiling Point: 394.7±42.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.1 mmHg at 25°C
Enthalpy of Vaporization: 74.5±6.0 kJ/mol
Flash Point: 215.4±26.5 °C
Index of Refraction: 1.546
Molar Refractivity: 56.2±0.3 cm3
#H bond acceptors: 5
#H bond donors: 4
#Freely Rotating Bonds: 4
#Rule of 5 Violations: 0
ACD/LogP: 0.46
ACD/LogD (pH 5.5): -2.21
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -0.84
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 7.08
Polar Surface Area: 84 Å2
Polarizability: 22.3±0.5 10-24cm3
Surface Tension: 56.6±3.0 dyne/cm
Molar Volume: 177.6±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) =  -1.08

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  389.58  (Adapted Stein & Brown method)
    Melting Pt (deg C):  145.21  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  4.23E-009  (Modified Grain method)
    Subcooled liquid VP: 7E-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: -1.08 (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:
       Aliphatic Amines

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.09E-013  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.220E-015 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -1.08  (KowWin est)
  Log Kaw used:  -11.068  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  9.988
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.1812
   Biowin2 (Non-Linear Model)     :   0.9818
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   3.3980  (days-weeks  )
   Biowin4 (Primary Survey Model) :   4.0302  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.8871
   Biowin6 (MITI Non-Linear Model):   0.6960
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.0367
 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):  9.33E-006 Pa (7E-008 mm Hg)
  Log Koa (Koawin est  ): 9.988
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.321 
       Octanol/air (Koa) model:  0.00239 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.921 
       Mackay model           :  0.963 
       Octanol/air (Koa) model:  0.16 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 152.7916 E-12 cm3/molecule-sec
      Half-Life =     0.070 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.840 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.942 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  10
      Log Koc:  1.000 

 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: -1.08 (estimated)

 Volatilization from Water:
    Henry LC:  2.09E-013 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 4.148E+009  hours   (1.728E+008 days)
    Half-Life from Model Lake : 4.525E+010  hours   (1.886E+009 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       0.000109        1.68         1000       
   Water     34.4            208          1000       
   Soil      65.5            416          1000       
   Sediment  0.0596          1.87e+003    0          
     Persistence Time: 387 hr




                    

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