ChemSpider 2D Image | Platanic acid | C29H46O4

Platanic acid

  • Molecular FormulaC29H46O4
  • Average mass458.673 Da
  • Monoisotopic mass458.339600 Da
  • ChemSpider ID58505
  • defined stereocentres - 10 of 10 defined stereocentres


More details:






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(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bS)-1-Acetyl-9-hydroxy-5a,5b,8,8,11a-pentamethylicosahydro-3aH-cyclopenta[a]chrysen-3a-carbonsäure [German] [ACD/IUPAC Name]
(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bS)-1-Acetyl-9-hydroxy-5a,5b,8,8,11a-pentamethylicosahydro-3aH-cyclopenta[a]chrysene-3a-carboxylic acid [ACD/IUPAC Name]
3aH-Cyclopenta[a]chrysene-3a-carboxylic acid, 1-acetyleicosahydro-9-hydroxy-5a,5b,8,8,11a-pentamethyl-, (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bS)- [ACD/Index Name]
Acide (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bS)-1-acétyl-9-hydroxy-5a,5b,8,8,11a-pentaméthylicosahydro-3aH-cyclopenta[a]chrysène-3a-carboxylique [French] [ACD/IUPAC Name]
Platanic acid
(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bS)-1-Acetyl-9-hydroxy-5a,5b,8,8,11a-pentamethyl-icosahydro-cyclopenta[a]chrysene-3a-carboxylic acid
30-Norlupan-28-oic acid, 3-hydroxy-20-oxo-, (3β)-
3-Hydroxy-20-oxonorlupan-28-oic acid, (3β)
3β-Hydroxy-20-oxo-30-norlupan-28-oic acid
6060-06-6 [RN]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

AIDS005860 [DBID]
AIDS-005860 [DBID]
  • Miscellaneous
    • Chemical Class:

      A pentacyclic triterpenoid that is 30-norlupan-28-oic acid substituted by a 3<stereo>beta</stereo>-hydroxy and an oxo group at position 20. It is isolated from the leaves of <ital>Syzygium claviflorum </ital> and exhibits anti-HIV activity. ChEBI CHEBI:65487
      A pentacyclic triterpenoid that is 30-norlupan-28-oic acid substituted by a 3beta-hydroxy and an oxo group at position 20. It is isolated from the leaves of Syzygium claviflorum; and exhibits anti-HI V activity. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:65487

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

Density: 1.1±0.1 g/cm3
Boiling Point: 568.1±25.0 °C at 760 mmHg
Vapour Pressure: 0.0±3.5 mmHg at 25°C
Enthalpy of Vaporization: 97.9±6.0 kJ/mol
Flash Point: 311.4±19.7 °C
Index of Refraction: 1.535
Molar Refractivity: 129.0±0.3 cm3
#H bond acceptors: 4
#H bond donors: 2
#Freely Rotating Bonds: 2
#Rule of 5 Violations: 1
ACD/LogP: 6.62
ACD/LogD (pH 5.5): 4.88
ACD/BCF (pH 5.5): 1633.20
ACD/KOC (pH 5.5): 3354.74
ACD/LogD (pH 7.4): 3.08
ACD/BCF (pH 7.4): 25.96
ACD/KOC (pH 7.4): 53.32
Polar Surface Area: 75 Å2
Polarizability: 51.1±0.5 10-24cm3
Surface Tension: 42.4±3.0 dyne/cm
Molar Volume: 414.5±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) =  5.54

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  537.51  (Adapted Stein & Brown method)
    Melting Pt (deg C):  230.12  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  8.19E-014  (Modified Grain method)
    Subcooled liquid VP: 1.31E-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):  0.1972
       log Kow used: 5.54 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  3.5071 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 :   2.68E-013  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  2.507E-013 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  5.54  (KowWin est)
  Log Kaw used:  -10.960  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  16.500
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :  -0.1522
   Biowin2 (Non-Linear Model)     :   0.0000
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.6270  (recalcitrant)
   Biowin4 (Primary Survey Model) :   2.9116  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.4201
   Biowin6 (MITI Non-Linear Model):   0.0172
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -2.3483
 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):  1.75E-009 Pa (1.31E-011 mm Hg)
  Log Koa (Koawin est  ): 16.500
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  1.72E+003 
       Octanol/air (Koa) model:  7.76E+003 
   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 =  46.5121 E-12 cm3/molecule-sec
      Half-Life =     0.230 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     2.760 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    :  1.647E+004
      Log Koc:  4.217 

 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 = 0.750 (BCF = 5.623)
       log Kow used: 5.54 (estimated)

 Volatilization from Water:
    Henry LC:  2.68E-013 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 4.679E+009  hours   (1.95E+008 days)
    Half-Life from Model Lake : 5.104E+010  hours   (2.127E+009 days)

 Removal In Wastewater Treatment:
    Total removal:              88.76  percent
    Total biodegradation:        0.75  percent
    Total sludge adsorption:    88.02  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       0.0144          5.52         1000       
   Water     2.23            4.32e+003    1000       
   Soil      64.6            8.64e+003    1000       
   Sediment  33.1            3.89e+004    0          
     Persistence Time: 9.11e+003 hr




                    

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