ChemSpider 2D Image | Oleanolic acid | C30H48O3

Oleanolic acid

  • Molecular FormulaC30H48O3
  • Average mass456.700 Da
  • Monoisotopic mass456.360352 Da
  • ChemSpider ID10062
  • defined stereocentres - 8 of 8 defined stereocentres


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(+)-Oleanolic acid
(3b)-3-Hydroxyolean-12-en-28-oic Acid
(3β)-3-hydroxy-Olean-12-en-28-oic acid
(3β)-3-Hydroxyolean-12-en-28-oic acid [ACD/IUPAC Name]
(3β)-3-Hydroxyolean-12-en-28-säure [German] [ACD/IUPAC Name]
(3β)-3-β-hydroxy-Olean-12-en-28-oic acid
(4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-Hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydro-4a(2H)-picencarbonsäure [German]
(4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-Hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydro-4a(2H)-picenecarboxylic acid
3β-hydroxy-Olean-12-en-28-oic acid
3β-hydroxy-Olean-12-en-28-oic acid
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

AIDS014809 [DBID]
AIDS-014809 [DBID]
CCRIS 6493 [DBID]
CHEBI:37659 [DBID]
NSC 114945 [DBID]
NSC114945 [DBID]
O5504_SIGMA [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Appearance:

      light yellow Indofine [020041S]
    • Safety:

      26-37-60 Alfa Aesar H60445
      36/37/38 Alfa Aesar H60445
      GHS07 Biosynth Q-100572
      H315; H319; H335 Biosynth Q-100572
      H315-H319-H335 Alfa Aesar H60445
      P261; P280; P302+P352; P304+P340; P305+P351+P338; P312 Biosynth Q-100572
      P261-P280-P305+P351+P338-P304+P340-P405-P501a Alfa Aesar H60445
      Warning Alfa Aesar H60445
      Warning Biosynth Q-100572
      Xi Abblis Chemicals AB1009824
    • Target Organs:

      Others TargetMol T2865
    • Compound Source:

      Isolated from a plant Susan Richardson [Structure found in ChemSpider, confirmed from ACD/Dictionary, The Merck Index Online, ChEBI and ChEMBL]
      Swartzia langsdorfii (Fabaceae), Styrax ferrugineus (Styracaceae), Rudgea jasminoides (Rubiaceae), Qualea grandiflora (Vochysiaceae), Alibertia macrophylla (Rubiaceae), Alibertia edulis (Rubiaceae) Susan Richardson [Structure found in ChemSpider, confirmed from ACD/Dictionary, The Merck Index Online, ChEBI and ChEMBL]
    • Bio Activity:

      GPBA receptor (TGR5) partial agonist (EC50 = 2.25 ?M; 72% efficacy). Displays no activity at FXR. Also inhibits protein phosphate 1B (PTP1B) and glycogen phosphorylase. Suppresses cell proliferation and increases apoptosis in T24 bladder cancer cells. Antidiabetic, antihyperglycaemic, antitumor and hepatoprotective. Tocris Bioscience 6026
      GPBA receptor (TGR5) partial agonist (EC50 = 2.25 muM; 72% efficacy). Displays no activity at FXR. Also inhibits protein phosphate 1B (PTP1B) and glycogen phosphorylase. Suppresses cell proliferation and increases apoptosis in T24 bladder cancer cells. Antidiabetic, antihyperglycaemic, antitumor and hepatoprotective. Tocris Bioscience 6026
      Oleanolic acid (Caryophyllin) is a natural compound from plants with anti-tumor activities. MedChem Express
      Oleanolic acid (Caryophyllin) is a natural compound from plants with anti-tumor activities.; IC50 value:; Target:; in vitro: OA suppressed the proliferation of lung cancer cells in both dose- and time-dependent manners, along with an increase in miR-122 abundance. MedChem Express HY-N0156
      Oleanolic acid (Caryophyllin) is a natural compound from plants with anti-tumor activities.;IC50 value:;Target:;In vitro: OA suppressed the proliferation of lung cancer cells in both dose- and time-dependent manners, along with an increase in miR-122 abundance. The suppression of miR-122 abolished the effect of OA on lung cancer cells. CCNG1 and MEF2D, two putative miR-122 targets, were found to be downregulated by OA treatment [1]. OA induced autophagy in normal tissue-derived cells without cytotoxicity. OA-induced autophagy was shown to decrease the proliferation of KRAS-transformed normal cells and to impair their invasion and anchorage-independent growth [2].;In vivo: Mouse model experiments also demonstrated that OA suppressed the growth of KRAS-transformed breast epithelial cell MCF10A-derived tumor xenograft by inducing autophagy [2]. activation of MAPK pathways, including p-38 MAPK, JNK and ERK, was triggered by OA in both a dose and time-dependent fashion in all the teste MedChem Express HY-N0156
      Others MedChem Express HY-N0156
      Others TargetMol T2865
      Selective GPBA receptor (TGR5) partial agonist Tocris Bioscience 6026

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

Density: 1.1±0.1 g/cm3
Boiling Point: 553.5±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±3.4 mmHg at 25°C
Enthalpy of Vaporization: 95.9±6.0 kJ/mol
Flash Point: 302.6±26.6 °C
Index of Refraction: 1.557
Molar Refractivity: 133.6±0.4 cm3
#H bond acceptors: 3
#H bond donors: 2
#Freely Rotating Bonds: 1
#Rule of 5 Violations: 1
ACD/LogP: 9.06
ACD/LogD (pH 5.5): 7.71
ACD/BCF (pH 5.5): 255162.84
ACD/KOC (pH 5.5): 141777.56
ACD/LogD (pH 7.4): 5.90
ACD/BCF (pH 7.4): 4017.71
ACD/KOC (pH 7.4): 2232.38
Polar Surface Area: 58 Å2
Polarizability: 53.0±0.5 10-24cm3
Surface Tension: 45.4±5.0 dyne/cm
Molar Volume: 414.9±5.0 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) =  7.95

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  525.28  (Adapted Stein & Brown method)
    Melting Pt (deg C):  224.41  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.99E-014  (Modified Grain method)
    MP  (exp database):  310 dec deg C
    Subcooled liquid VP: 3.13E-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):  0.001748
       log Kow used: 7.95 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  0.082343 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 :   9.66E-010  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  6.841E-012 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  7.95  (KowWin est)
  Log Kaw used:  -7.403  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  15.353
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :  -0.3420
   Biowin2 (Non-Linear Model)     :   0.0000
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.4417  (recalcitrant)
   Biowin4 (Primary Survey Model) :   2.7832  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.3575
   Biowin6 (MITI Non-Linear Model):   0.0161
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -2.5226
 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):  4.17E-009 Pa (3.13E-011 mm Hg)
  Log Koa (Koawin est  ): 15.353
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  719 
       Octanol/air (Koa) model:  553 
   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 = 123.0250 E-12 cm3/molecule-sec
      Half-Life =     0.087 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.043 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     7.393750 E-17 cm3/molecule-sec
      Half-Life =     0.155 Days (at 7E11 mol/cm3)
      Half-Life =      3.720 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    :  2.532E+005
      Log Koc:  5.404 

 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: 7.95 (estimated)

 Volatilization from Water:
    Henry LC:  9.66E-010 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.295E+006  hours   (5.397E+004 days)
    Half-Life from Model Lake : 1.413E+007  hours   (5.888E+005 days)

 Removal In Wastewater Treatment:
    Total removal:              94.01  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       0.00552         1.34         1000       
   Water     0.75            4.32e+003    1000       
   Soil      40.2            8.64e+003    1000       
   Sediment  59              3.89e+004    0          
     Persistence Time: 1.08e+004 hr




                    

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