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
The Merck Index Online

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]
25488-53-3 [RN]
3β-hydroxy-lup-20(29)-en-28-oic acid
3β-Hydroxy-20(29)-lupaene-28-oic acid
472-15-1 [RN]
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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]
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  • Experimental Physico-chemical Properties
  • Predicted Physico-chemical Properties
  • Miscellaneous

    • Safety:

      IRRITANT Matrix Scientific 090209

    • 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
      A pentacyclic triterpenoid that is lupane having a double bond at position 20(29) as well as 3beta-hydroxy and 28-carboxy substituents. It is found in the bark and other plant parts o; f several speci es of plants including Syzygium claviflorum. It exhibits anti-HIV, antimalarial, antineoplastic and anti-inflammatory properties. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:3087

    • Compound Source:

      Amaranthus hypochondriacus PlantCyc CPD-14493
      Anacardium occidentale PlantCyc CPD-14493
      Aquilegia coerulea PlantCyc CPD-14493
      Arabidopsis halleri PlantCyc CPD-14493
      Arabidopsis lyrata PlantCyc CPD-14493
      Arabidopsis thaliana col PlantCyc CPD-14493
      Beta vulgaris subsp. vulgaris PlantCyc CPD-14493
      betulinate biosynthesis PlantCyc CPD-14493
      Boechera stricta PlantCyc CPD-14493
      Brachypodium distachyon PlantCyc CPD-14493
      Calotropis gigantea PlantCyc CPD-14493
      Camptotheca acuminata PlantCyc CPD-14493
      Cannabis sativa PlantCyc CPD-14493
      Capsella rubella PlantCyc CPD-14493
      Capsicum annuum PlantCyc CPD-14493
      Carica papaya PlantCyc CPD-14493
      Catharanthus roseus PlantCyc CPD-14493
      Chenopodium quinoa PlantCyc CPD-14493
      Cicer arietinum PlantCyc CPD-14493
      Citrus clementina PlantCyc CPD-14493
      Citrus sinensis PlantCyc CPD-14493
      Corchorus capsularis PlantCyc CPD-14493
      Cucumis sativus PlantCyc CPD-14493
      Daucus carota subsp. sativus PlantCyc CPD-14493
      Dianthus caryophyllus PlantCyc CPD-14493
      Eucalyptus grandis PlantCyc CPD-14493
      Eutrema salsugineum PlantCyc CPD-14493
      Fragaria vesca subsp. vesca PlantCyc CPD-14493
      Glycine max PlantCyc CPD-14493
      Gossypium raimondii PlantCyc CPD-14493
      Helianthus annuus PlantCyc CPD-14493
      Humulus lupulus var. lupulus PlantCyc CPD-14493
      Isolated from a plant Susan Richardson [Structure found in ChemSpider, confirmed from ACD/Dictionary, The Merck Index Online, ChEBI and ChEMBL]
      Kalanchoe fedtschenkoi PlantCyc CPD-14493
      Kalanchoe laxiflora PlantCyc CPD-14493
      Linum usitatissimum PlantCyc CPD-14493
      Lotus japonicus PlantCyc CPD-14493
      lupeol + 3 NADPH + 3 oxygen + 3 H+ -> betulinate + 3 NADP+ + 4 H2O + H+ PlantCyc CPD-14493
      Malus domestica PlantCyc CPD-14493
      Manihot esculenta PlantCyc CPD-14493
      Medicago truncatula PlantCyc CPD-14493
      Mimulus guttatus PlantCyc CPD-14493
      Nicotiana tabacum PlantCyc CPD-14493
      Olea europaea var. sylvestris PlantCyc CPD-14493
      Oropetium thomaeum PlantCyc CPD-14493
      Oryza glaberrima PlantCyc CPD-14493
      Oryza punctata PlantCyc CPD-14493
      Oryza rufipogon PlantCyc CPD-14493
      Oryza sativa Japonica Group PlantCyc CPD-14493
      Panicum hallii PlantCyc CPD-14493
      Panicum virgatum PlantCyc CPD-14493
      Petunia axillaris PlantCyc CPD-14493
      Phaseolus vulgaris PlantCyc CPD-14493
      Populus trichocarpa PlantCyc CPD-14493
      Prunus persica PlantCyc CPD-14493
      Ricinus communis PlantCyc CPD-14493
      Rosa chinensis PlantCyc CPD-14493
      Rosa multiflora PlantCyc CPD-14493
      Salvia miltiorrhiza PlantCyc CPD-14493
      Solanum lycopersicum PlantCyc CPD-14493
      Solanum melongena PlantCyc CPD-14493
      Solanum pennellii PlantCyc CPD-14493
      Solanum tuberosum PlantCyc CPD-14493
      Spinacia oleracea PlantCyc CPD-14493
      Stemodia foliosa (Scrophulariaceae) Susan Richardson [Structure found in ChemSpider, confirmed from ACD/Dictionary, The Merck Index Online, ChEBI and ChEMBL]
      Thellungiella parvula PlantCyc CPD-14493
      Theobroma cacao PlantCyc CPD-14493
      Trifolium pratense PlantCyc CPD-14493
      Triticum aestivum PlantCyc CPD-14493
      Vitis vinifera PlantCyc CPD-14493

    • Bio Activity:

      Anti-HIV compound. Anticancer compound. Apoptosis inducer. Modulator of NF-kappaB. Potent DNA topoisomerase II inhibitor. Potent proteasome activator. Antimalarial compound. Hello Bio [HB3799]
      Apoptosis MedChem Express HY-10529
      Apoptosis inducer MedChem Express HY-10529
      Apoptosis inducer Hello Bio [HB3799]
      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
      betulinic aldehyde + NADPH + oxygen -> betulinate + NADP+ + H2O PlantCyc CPD-14493
      Biochemicals & small molecules Hello Bio [HB3799]
      Cell signaling/Cytokines & NF-&kappa;B/NF-&kappa;B Hello Bio [HB3799]
      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

Click to predict properties on the Chemicalize site


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