ChemSpider 2D Image | Stigmasterol | C29H48O


  • Molecular FormulaC29H48O
  • Average mass412.691 Da
  • Monoisotopic mass412.370514 Da
  • ChemSpider ID4444352
  • Double-bond stereo - Double-bond stereo

    defined stereocentres - 9 of 9 defined stereocentres

More details:

Featured data source

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

(3S,8S,9S,10R,13R,14S,17R)-17-[(2R,3E,5S)-5-éthyl-6-méthyl-3-heptèn-2-yl]-10,13-diméthyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tétradécahydro-1H-cyclopenta[a]phénanthrén-3-ol [French]
(3β,20R,22E,24S)-Stigmasta-5,22-dien-3-ol [German] [ACD/IUPAC Name]

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

AIDS002709 [DBID]
AIDS-002709 [DBID]
C05442 [DBID]
LMST01040123 [DBID]
NSC 8095 [DBID]
ZINC04096712 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      IRRITANT Matrix Scientific 085952
    • Target Organs:

      Others TargetMol T2967
    • Chemical Class:

      A 3<stereo>beta</stereo>-sterol that consists of 3<stereo>beta</stereo>-hydroxystigmastane having double bonds at the 5,6- and 22,23-positions. ChEBI CHEBI:28824
      A 3beta-sterol that consists of 3beta-hydroxystigmastane having double bonds at the 5,6- and 22,23-positions. ChEBI
    • Compound Source:

      Aegilops tauschii PlantCyc CPD-4162
      Amaranthus hypochondriacus PlantCyc CPD-4162
      Amborella trichopoda PlantCyc CPD-4162
      Anacardium occidentale PlantCyc CPD-4162
      Ananas comosus PlantCyc CPD-4162
      Aquilegia coerulea PlantCyc CPD-4162
      Arabidopsis halleri PlantCyc CPD-4162
      Arabidopsis lyrata PlantCyc CPD-4162
      Arabidopsis thaliana col PlantCyc CPD-4162
      Asparagus officinalis PlantCyc CPD-4162
      Beta vulgaris subsp. vulgaris PlantCyc CPD-4162
      Boechera stricta PlantCyc CPD-4162
      Brachypodium distachyon PlantCyc CPD-4162
      Brassica napus PlantCyc CPD-4162
      Brassica oleracea var. capitata PlantCyc CPD-4162
      Brassica oleracea var. oleracea PlantCyc CPD-4162
      Brassica rapa FPsc PlantCyc CPD-4162
      Brassica rapa subsp. pekinensis PlantCyc CPD-4162
      Calotropis gigantea PlantCyc CPD-4162
      Camptotheca acuminata PlantCyc CPD-4162
      Cannabis sativa PlantCyc CPD-4162
      Capsella grandiflora PlantCyc CPD-4162
      Capsella rubella PlantCyc CPD-4162
      Capsicum annuum PlantCyc CPD-4162
      Carica papaya PlantCyc CPD-4162
      Catharanthus roseus PlantCyc CPD-4162
      Chenopodium quinoa PlantCyc CPD-4162
      Cicer arietinum PlantCyc CPD-4162
      Citrus clementina PlantCyc CPD-4162
      Citrus sinensis PlantCyc CPD-4162
      Corchorus capsularis PlantCyc CPD-4162
      Cucumis sativus PlantCyc CPD-4162
      Daucus carota subsp. sativus PlantCyc CPD-4162
      Dianthus caryophyllus PlantCyc CPD-4162
      Dioscorea rotundata PlantCyc CPD-4162
      Eucalyptus grandis PlantCyc CPD-4162
      Eutrema salsugineum PlantCyc CPD-4162
      Fragaria vesca subsp. vesca PlantCyc CPD-4162
      Glycine max PlantCyc CPD-4162
      Gossypium raimondii PlantCyc CPD-4162
      Helianthus annuus PlantCyc CPD-4162
      Hordeum vulgare subsp. vulgare PlantCyc CPD-4162
      Humulus lupulus var. lupulus PlantCyc CPD-4162
      Isolated from a plant Susan Richardson [Structure found in ChemSpider, confirmed from ACD/Dictionary, ChEMBL and The Merck Index Online]
      Kalanchoe fedtschenkoi PlantCyc CPD-4162
      Kalanchoe laxiflora PlantCyc CPD-4162
      Leersia perrieri PlantCyc CPD-4162
      Linum usitatissimum PlantCyc CPD-4162
      Lotus japonicus PlantCyc CPD-4162
      Malus domestica PlantCyc CPD-4162
      Manihot esculenta PlantCyc CPD-4162
      Medicago truncatula PlantCyc CPD-4162
      Mimulus guttatus PlantCyc CPD-4162
      Miscanthus sinensis PlantCyc CPD-4162
      Musa acuminata PlantCyc CPD-4162
      Nicotiana tabacum PlantCyc CPD-4162
      Olea europaea var. sylvestris PlantCyc CPD-4162
      Oropetium thomaeum PlantCyc CPD-4162
      Oryza brachyantha PlantCyc CPD-4162
      Oryza glaberrima PlantCyc CPD-4162
      Oryza punctata PlantCyc CPD-4162
      Oryza rufipogon PlantCyc CPD-4162
      Oryza sativa Japonica Group PlantCyc CPD-4162
      Panicum hallii PlantCyc CPD-4162
      Panicum virgatum PlantCyc CPD-4162
      Petunia axillaris PlantCyc CPD-4162
      Phaseolus vulgaris PlantCyc CPD-4162
      Physcomitrella patens PlantCyc CPD-4162
      plant sterol biosynthesis PlantCyc CPD-4162
      Populus trichocarpa PlantCyc CPD-4162
      Prunus persica PlantCyc CPD-4162
      Pterogyne nitens (Fabaceae), Styrax ferrugineus (Styracaceae), Ocotea odorifera (Lauraceae), Stemodia foliosa (Scrophulariaceae), Toona ciliata (Meliacee), Rudgea jasminoides (Rubiaceae), Alibertia ma crophylla (Rubiaceae), Arrabidaea samydoides (Bignoniaceae), Cupania vernalis (Sapindaceae) Susan Richardson [Structure found in ChemSpider, confirmed from ACD/Dictionary, ChEMBL and The Merck Index Online]
      Ricinus communis PlantCyc CPD-4162
      Rosa chinensis PlantCyc CPD-4162
      Rosa multiflora PlantCyc CPD-4162
      Salvia miltiorrhiza PlantCyc CPD-4162
      Selaginella moellendorffii PlantCyc CPD-4162
      Setaria italica PlantCyc CPD-4162
      Setaria viridis PlantCyc CPD-4162
      Solanum lycopersicum PlantCyc CPD-4162
      Solanum melongena PlantCyc CPD-4162
      Solanum pennellii PlantCyc CPD-4162
      Solanum tuberosum PlantCyc CPD-4162
      Sorghum bicolor PlantCyc CPD-4162
      Sphagnum fallax PlantCyc CPD-4162
      Spinacia oleracea PlantCyc CPD-4162
      Spirodela polyrhiza PlantCyc CPD-4162
      Thellungiella parvula PlantCyc CPD-4162
      Theobroma cacao PlantCyc CPD-4162
      Trifolium pratense PlantCyc CPD-4162
      Triticum aestivum PlantCyc CPD-4162
      Triticum urartu PlantCyc CPD-4162
      Vitis vinifera PlantCyc CPD-4162
      Zea mays subsp. mays PlantCyc CPD-4162
      Zostera marina PlantCyc CPD-4162
    • Bio Activity:

      Anti-hypercholestrolemic compound. Anti-inflammatory and immune-modulating effects. Anticancer compound. Chemopreventive. Cytostatic. Cell growth inhibitor. Antimutagenic. Potent in vitro antagonist of FXR (farnesoid X receptor). DNA polymerase beta inhibitor. Potent antioxidant, hypoglycemic and thyroid inhibiting agent. Anti-osteoarthritic. Decreases the expression of matrix metalloproteinases. Neuroprotective. Is used as a precursor for synthetic progesterone and vitamin D3 and is an intermediate in the biosynthesis of androgens, estrogens and corticoids. Hello Bio [HB4095]
      Biochemicals & small molecules/Antagonists & inhibitors Hello Bio [HB4095]
      Others TargetMol T2967
      Phytosterol with anticancer and many other biological actions. Farnesoid X receptor antagonist. Hello Bio [HB4095]
      Receptors & Transporters/Nuclear hormone/Farnesoid X Hello Bio [HB4095]
      sitosterol + a reduced [NADPH-hemoprotein reductase] + oxygen -> stigmasterol + an oxidized [NADPH-hemoprotein reductase] + 2 H2O PlantCyc CPD-4162

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

Density: 1.0±0.1 g/cm3
Boiling Point: 501.1±19.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.9 mmHg at 25°C
Enthalpy of Vaporization: 88.7±6.0 kJ/mol
Flash Point: 219.4±13.7 °C
Index of Refraction: 1.531
Molar Refractivity: 129.1±0.4 cm3
#H bond acceptors: 1
#H bond donors: 1
#Freely Rotating Bonds: 5
#Rule of 5 Violations: 1
ACD/LogP: 10.21
ACD/LogD (pH 5.5): 8.81
ACD/BCF (pH 5.5): 1000000.00
ACD/KOC (pH 5.5): 1469993.75
ACD/LogD (pH 7.4): 8.81
ACD/BCF (pH 7.4): 1000000.00
ACD/KOC (pH 7.4): 1469993.75
Polar Surface Area: 20 Å2
Polarizability: 51.2±0.5 10-24cm3
Surface Tension: 38.2±5.0 dyne/cm
Molar Volume: 417.6±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) =  9.43

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  452.55  (Adapted Stein & Brown method)
    Melting Pt (deg C):  171.80  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.62E-010  (Modified Grain method)
    MP  (exp database):  170 deg C
    Subcooled liquid VP: 5.1E-009 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):  7.277e-005
       log Kow used: 9.43 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  0.0012037 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.59E-004  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.209E-006 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  9.43  (KowWin est)
  Log Kaw used:  -1.975  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  11.405
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.3419
   Biowin2 (Non-Linear Model)     :   0.0056
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.0229  (months      )
   Biowin4 (Primary Survey Model) :   3.0749  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.0808
   Biowin6 (MITI Non-Linear Model):   0.0024
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.6320
 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):  6.8E-007 Pa (5.1E-009 mm Hg)
  Log Koa (Koawin est  ): 11.405
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  4.41 
       Octanol/air (Koa) model:  0.0624 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.994 
       Mackay model           :  0.997 
       Octanol/air (Koa) model:  0.833 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 185.1721 E-12 cm3/molecule-sec [Cis-isomer]
      OVERALL OH Rate Constant = 192.7721 E-12 cm3/molecule-sec [Trans-isomer]
      Half-Life =    0.693 Hrs (12-hr day; 1.5E6 OH/cm3) [Cis-isomer]
      Half-Life =    0.666 Hrs (12-hr day; 1.5E6 OH/cm3) [Trans-isomer]
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    20.393749 E-17 cm3/molecule-sec [Cis-]
      OVERALL Ozone Rate Constant =    27.393749 E-17 cm3/molecule-sec [Trans-]
      Half-Life =     1.349 Hrs (at 7E11 mol/cm3) [Cis-isomer]
      Half-Life =     1.004 Hrs (at 7E11 mol/cm3) [Trans-isomer]
   Fraction sorbed to airborne particulates (phi): 0.995 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  4.526E+006
      Log Koc:  6.656 

 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 = 1.478 (BCF = 30.04)
       log Kow used: 9.43 (estimated)

 Volatilization from Water:
    Henry LC:  0.000259 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River:      6.665  hours
    Half-Life from Model Lake :      243.1  hours   (10.13 days)

 Removal In Wastewater Treatment:
    Total removal:              94.03  percent
    Total biodegradation:        0.78  percent
    Total sludge adsorption:    93.26  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       0.00671         0.684        1000       
   Water     1.39            1.44e+003    1000       
   Soil      30.1            2.88e+003    1000       
   Sediment  68.5            1.3e+004     0          
     Persistence Time: 4.72e+003 hr


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