ChemSpider 2D Image | Orlistat | C29H53NO5

Orlistat

  • Molecular FormulaC29H53NO5
  • Average mass495.735 Da
  • Monoisotopic mass495.392365 Da
  • ChemSpider ID2298564
  • defined stereocentres - 4 of 4 defined stereocentres


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(-)-Tetrahydrolipstatin
(−)-Tetrahydrolipstatin
(1S)-1-{[(2S,3S)-3-hexyl-4-oxooxetan-2-yl]methyl}dodecyl (2S)-2-(formylamino)-4-methylpentanoate
(1S)-1-{[(2S,3S)-3-hexyl-4-oxooxetan-2-yl]methyl}dodecyl N-formyl-L-leucinate
(1S)-1-{[(2S,3S)-3-Hexyl-4-oxooxetan-2-yl]methyl}dodecyl-(2S)-2-(formylamino)-4-methylpentanoat [German]
(2S)-1-[(2S,3S)-3-Hexyl-4-oxo-2-oxetanyl]-2-tridecanyl N-formyl-L-leucinate [ACD/IUPAC Name]
(2S)-1-[(2S,3S)-3-Hexyl-4-oxo-2-oxetanyl]-2-tridecanyl-N-formyl-L-leucinat [German] [ACD/IUPAC Name]
(2S)-1-[(2S,3S)-3-Hexyl-4-oxooxetan-2-yl]tridecan-2-yl N-formyl-L-leucinate
(2S)-2-(formylamino)-4-méthylpentanoate de (1S)-1-{[(2S,3S)-3-hexyl-4-oxooxétan-2-yl]méthyl}dodécyle [French]
[2S-[2a(R*),3b]]-N-Formyl-L-leucine 1-[(3-hexyl-4-oxo-2-oxetanyl)methyl]dodecyl ester
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

95M8R751W8 [DBID]
D04028 [DBID]
LS-178328 [DBID]
O4139_SIGMA [DBID]
PubChem Substance ID 329831176 [DBID]
R-212 [DBID]
UNII:95M8R751W8 [DBID]
UNII-95M8R751W8 [DBID]
  • Experimental Physico-chemical Properties
  • Predicted Physico-chemical Properties
  • Miscellaneous
    • Safety:

      A08AB01 Wikidata Q424163
      P261; P262 Biosynth Q-201519
    • Target Organs:

      Fatty acid synthase inhibitor; triacylglycerol lipase inhibitor TargetMol T0686
    • Chemical Class:

      A carboxylic ester resulting from the formal condensation of the carboxy group of <element>N</element>-formyl-<stereo>L</stereo>-leucine with the hydroxy group of (3<stereo>S</stereo>,4<stereo>S</ster eo>)-3-hexyl-4-[(2<stereo>S</stereo>)-2-hydroxytridecyl]oxetan-2-one. A pancreatic lipase inhibitor, it is used as an anti-obesity drug. ChEBI CHEBI:94686
    • Drug Status:

      approved BIONET-Key Organics KS-1183
    • Bio Activity:

      Enzymes Tocris Bioscience 3540
      Esterases Tocris Bioscience 3540
      Fatty acid synthase; triacylglycerol lipase TargetMol T0686
      Hypolipemic pancreatic, gastric and carboxylester lipase inhibitor. Exhibits no activity at phospholipase A2, liver esterase, trypsin and chymotrypsin. Inhibits the thioesterase domain of fatty acid s ynthase, leading to cell cycle arrest at the G1/S boundary in vitro. Prevents the absorption of approximately one third of fat from food and exhibits progastrokinetic, antiobesity and antihypercholest erolemic activity in vivo. Tocris Bioscience 3540
      Hypolipemic pancreatic, gastric and carboxylester lipase inhibitor. Exhibits no activity at phospholipase A2, liver esterase, trypsin and chymotrypsin. Inhibits the thioesterase domain of fatty acid synthase, leading to cell cycle arrest at the G1/S boundary in vitro. Prevents the absorption of approximately one third of fat from food and exhibits progastrokinetic, antiobesity and antihypercholesterolemic activity in vivo. Tocris Bioscience 3540
      Lipases Tocris Bioscience 3540
      Metabolism TargetMol T0686
      Orlistat is a general lipase inhibitor with IC50 of 122 ng/ml for PL from human duodenal juice. MedChem Express
      Orlistat is a general lipase inhibitor with IC50 of 122 ng/ml for PL from human duodenal juice.; Target: lipase inhibitor; Orlistat (also known as tetrahydrolipstatin) is a drug designed to treat obesity. MedChem Express HY-B0218
      Orlistat is a general lipase inhibitor with IC50 of 122 ng/ml for PL from human duodenal juice.;Target: lipase inhibitorOrlistat (also known as tetrahydrolipstatin) is a drug designed to treat obesity. It is marketed as a prescription drug under the trade name Xenical by Roche in most countries, and is sold over-the-counter as Alli by GlaxoSmithKline in the United Kingdom and the United States. Its primary function is preventing the absorption of fats from the human diet by acting as a lipase inhibitor, thereby reducing caloric intake. It is intended for use in conjunction with a healthcare provider-supervised reduced-calorie diet.Orlistat is the saturated derivative of lipstatin, a potent natural inhibitor of pancreatic lipases isolated from the bacterium Streptomyces toxytricini. However, due to its relative simplicity and stability, orlistat was chosen over lipstatin for development as an anti-obesity drug. The effectiveness of orlistat in promoting weight loss is definite, th MedChem Express HY-B0218
      Others MedChem Express HY-B0218
      Pancreatic, gastric and carboxylester lipase inhibitor; antiobesity and antihypercholesterolemic activity Tocris Bioscience 3540

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

Density: 1.0±0.1 g/cm3
Boiling Point: 615.9±30.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.8 mmHg at 25°C
Enthalpy of Vaporization: 91.4±3.0 kJ/mol
Flash Point: 326.3±24.6 °C
Index of Refraction: 1.470
Molar Refractivity: 141.6±0.3 cm3
#H bond acceptors: 6
#H bond donors: 1
#Freely Rotating Bonds: 23
#Rule of 5 Violations: 1
ACD/LogP: 8.94
ACD/LogD (pH 5.5): 8.95
ACD/BCF (pH 5.5): 1000000.00
ACD/KOC (pH 5.5): 1773130.38
ACD/LogD (pH 7.4): 8.95
ACD/BCF (pH 7.4): 1000000.00
ACD/KOC (pH 7.4): 1773130.38
Polar Surface Area: 82 Å2
Polarizability: 56.1±0.5 10-24cm3
Surface Tension: 35.7±3.0 dyne/cm
Molar Volume: 507.6±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) =  8.19

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  609.93  (Adapted Stein & Brown method)
    Melting Pt (deg C):  263.95  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  9.77E-014  (Modified Grain method)
    Subcooled liquid VP: 4.06E-011 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):  7.665e-005
       log Kow used: 8.19 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  0.0001519 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.13E-009  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  8.314E-010 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  8.19  (KowWin est)
  Log Kaw used:  -7.335  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  15.525
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.2869
   Biowin2 (Non-Linear Model)     :   1.0000
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.9265  (weeks       )
   Biowin4 (Primary Survey Model) :   4.3340  (hours-days  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.7660
   Biowin6 (MITI Non-Linear Model):   0.6928
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.3187
 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):  5.41E-009 Pa (4.06E-011 mm Hg)
  Log Koa (Koawin est  ): 15.525
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  554 
       Octanol/air (Koa) model:  822 
   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 =  45.1938 E-12 cm3/molecule-sec
      Half-Life =     0.237 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     2.840 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   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    :  4.772E+005
      Log Koc:  5.679 

 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 = 1.674 (BCF = 47.23)
       log Kow used: 8.19 (estimated)

 Volatilization from Water:
    Henry LC:  1.13E-009 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.154E+006  hours   (4.807E+004 days)
    Half-Life from Model Lake : 1.259E+007  hours   (5.244E+005 days)

 Removal In Wastewater Treatment:
    Total removal:              94.02  percent
    Total biodegradation:        0.78  percent
    Total sludge adsorption:    93.24  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       0.157           5.68         1000       
   Water     3.63            360          1000       
   Soil      30.8            720          1000       
   Sediment  65.4            3.24e+003    0          
     Persistence Time: 1.31e+003 hr




                    

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