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Search term: 472-15-1 (Found by approved synonym)

ChemSpider 2D Image | Betulinic acid | C30H48O3

Betulinic acid

  • Molecular FormulaC30H48O3
  • Average mass456.700 Da
  • Monoisotopic mass456.360352 Da
  • ChemSpider ID58496
  • defined stereocentres - 10 of 10 defined stereocentres


More details:



Featured data source



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

(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-Hydroxy-1-isopropenyl-5a,5b,8,8,11a-pentamethylicosahydro-3aH-cyclopenta[a]chrysen-3a-carbonsäure [German]
(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-Hydroxy-1-isopropenyl-5a,5b,8,8,11a-pentamethylicosahydro-3aH-cyclopenta[a]chrysene-3a-carboxylic acid
(3b)-3-hydroxylup-20(29)-en-28-oic Acid
(3β)-3-Hydroxylup-20(29)-en-28-oic acid [ACD/IUPAC Name]
(3β)-3-Hydroxylup-20(29)-en-28-säure [German] [ACD/IUPAC Name]
207-448-8 [EINECS]
472-15-1 [RN]
4G6A18707N
Acide (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-5a,5b,8,8,11a-pentaméthyl-1-(1-propèn-2-yl)icosahydro-3aH-cyclopenta[a]chrysène-3a-carboxylique [French]
Acide (3β)-3-hydroxylup-20(29)-én-28-oïque [French] [ACD/IUPAC Name]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

855057_ALDRICH [DBID]
AIDS005859 [DBID]
AIDS-005859 [DBID]
C08619 [DBID]
CCRIS 6748 [DBID]
NSC 113090 [DBID]
NSC 677578 [DBID]
NSC113090 [DBID]
NSC677578 [DBID]
Prestwick_95 [DBID]
More...
  • Experimental Physico-chemical Properties
  • Predicted Physico-chemical Properties
  • Miscellaneous
    • Safety:

      GHS07 Biosynth Q-100500
      H315; H319; H335 Biosynth Q-100500
      IRRITANT Matrix Scientific 090209
      P261; P280; P302+P352; P304+P340; P305+P351+P338; P312 Biosynth Q-100500
      Warning Biosynth Q-100500
    • Target Organs:

      Topoisomerase inhibitor TargetMol T2830
    • Chemical Class:

      A pentacyclic triterpenoid that is lupane having a double bond at position 20(29) as well as 3<stereo>beta</stereo>-hydroxy and 28-carboxy substituents. It is found in the bark and other plant parts o f several species of plants including <ital>Syzygium claviflorum</ital>. It exhibits anti-HIV, antimalarial, antineoplastic and anti-inflammatory properties. ChEBI CHEBI:3087
    • Compound Source:

      Isolated from a plant Susan Richardson [Structure found in ChemSpider, confirmed from ACD/Dictionary, The Merck Index Online, ChEBI and ChEMBL]
      Stemodia foliosa (Scrophulariaceae) Susan Richardson [Structure found in ChemSpider, confirmed from ACD/Dictionary, The Merck Index Online, ChEBI and ChEMBL]
    • Bio Activity:

      Apoptosis MedChem Express HY-10529
      Apoptosis inducer MedChem Express HY-10529
      Apoptosis inducer Topoisomerase MedChem Express HY-10529
      Apoptosis; Cell Cycle/DNA Damage; MedChem Express HY-10529
      Betulinic acid, a pentacyclic triterpene, selectively induces apoptosis in tumor cells, also is a inhibitor of HIV-1 with EC50 of 1.4 ? M.; IC50 Value: 1.4 ?M (EC50, HIV1); Target: Apoptosis inducer; Topoisomerase; in vitro: Betulinic acid shows anti-HIV activity by blocking HIV replication in H9 lymphocytes with an EC50 value of 1.4 ?M and inhibiting uninfected H9 cell growth with an IC50 value of 13 ?M. MedChem Express HY-10529
      DNA Damage/DNA Repair TargetMol T2830
      HIV-1;Eukaryotic topoisomerase I;Aminopeptidase N TargetMol T2830

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

Density: 1.1±0.1 g/cm3
Boiling Point: 550.0±33.0 °C at 760 mmHg
Vapour Pressure: 0.0±3.4 mmHg at 25°C
Enthalpy of Vaporization: 95.4±6.0 kJ/mol
Flash Point: 300.5±21.9 °C
Index of Refraction: 1.533
Molar Refractivity: 133.2±0.3 cm3
#H bond acceptors: 3
#H bond donors: 2
#Freely Rotating Bonds: 2
#Rule of 5 Violations: 1
ACD/LogP: 8.94
ACD/LogD (pH 5.5): 6.90
ACD/BCF (pH 5.5): 61787.45
ACD/KOC (pH 5.5): 50506.77
ACD/LogD (pH 7.4): 5.10
ACD/BCF (pH 7.4): 971.45
ACD/KOC (pH 7.4): 794.09
Polar Surface Area: 58 Å2
Polarizability: 52.8±0.5 10-24cm3
Surface Tension: 40.0±3.0 dyne/cm
Molar Volume: 428.8±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) =  8.00

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  522.42  (Adapted Stein & Brown method)
    Melting Pt (deg C):  223.07  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.91E-013  (Modified Grain method)
    Subcooled liquid VP: 3.84E-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):  0.001607
       log Kow used: 8.00 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  0.043947 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 :   8.18E-010  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.088E-010 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  8.00  (KowWin est)
  Log Kaw used:  -7.476  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  15.476
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :  -0.1581
   Biowin2 (Non-Linear Model)     :   0.0000
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.6539  (recalcitrant)
   Biowin4 (Primary Survey Model) :   2.9366  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.3206
   Biowin6 (MITI Non-Linear Model):   0.0085
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -2.1034
 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):  5.12E-009 Pa (3.84E-011 mm Hg)
  Log Koa (Koawin est  ): 15.476
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  586 
       Octanol/air (Koa) model:  735 
   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 =  91.4372 E-12 cm3/molecule-sec
      Half-Life =     0.117 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.404 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     1.200000 E-17 cm3/molecule-sec
      Half-Life =     0.955 Days (at 7E11 mol/cm3)
      Half-Life =     22.920 Hrs
   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    :  2.913E+005
      Log Koc:  5.464 

 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 = 1.000 (BCF = 10)
       log Kow used: 8.00 (estimated)

 Volatilization from Water:
    Henry LC:  8.18E-010 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River:  1.53E+006  hours   (6.373E+004 days)
    Half-Life from Model Lake : 1.669E+007  hours   (6.953E+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       0.00956         2.5          1000       
   Water     0.74            4.32e+003    1000       
   Soil      41              8.64e+003    1000       
   Sediment  58.3            3.89e+004    0          
     Persistence Time: 1.1e+004 hr




                    

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