ChemSpider 2D Image | (+)-5-epi-aristolochene | C15H24

(+)-5-epi-aristolochene

  • Molecular FormulaC15H24
  • Average mass204.351 Da
  • Monoisotopic mass204.187805 Da
  • ChemSpider ID4574150

  • defined stereocentres - 3 of 3 defined stereocentres

More details:

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

(+)-5-epi-aristolochene
(4R,4aR,6R)-6-Isopropényl-4,4a-diméthyl-1,2,3,4,4a,5,6,7-octahydronaphtalène [French] [ACD/IUPAC Name]
(4R,4aR,6R)-6-Isopropenyl-4,4a-dimethyl-1,2,3,4,4a,5,6,7-octahydronaphthalene [ACD/IUPAC Name]
(4R,4aR,6R)-6-Isopropenyl-4,4a-dimethyl-1,2,3,4,4a,5,6,7-octahydronaphthalin [German] [ACD/IUPAC Name]
Naphthalene, 1,2,3,4,6,7,8,8a-octahydro-1,8a-dimethyl-7-(1-methylethenyl)-, (1R,7R,8aR)- [ACD/Index Name]
(+)-5-epi-aristolochene
(4R,4aR,6R)-4,4a-dimethyl-6-(prop-1-en-2-yl)-1,2,3,4,4a,5,6,7-octahydronaphthalene
(4R,4aR,6R)-4,4a-dimethyl-6-(prop-1-en-2-yl)-1,2,3,4,4a,5,6,7-octahydronaphthalene 4βH-eremophila-9,11-diene
(4R,4aR,6R)-4,4a-dimethyl-6-(prop-1-en-2-yl)-1,2,3,4,4a,5,6,7-octahydronaphthalene; 4βH-eremophila-9,11-diene
3588800 [Beilstein]
More...

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

3588800; 6500129 [DBID]
CHEBI:23925 [DBID]
  • Miscellaneous

    • Chemical Class:

      A sesquiterpene that is 1,2,3,4,4a,5,6,7-octahydronaphthalene substituted by methyl groups at positions 4 and 4a and a prop-1-en-2-yl group at position 6 (the 4<stereo>R</stereo>,4a<stereo>R</stereo>, 6<stereo>R</stereo>-stereoisomer). ChEBI CHEBI:23925
      A sesquiterpene that is 1,2,3,4,4a,5,6,7-octahydronaphthalene substituted by methyl groups at positions 4 and 4a and a prop-1-en-2-yl group at position 6 (the 4R,4aR,; 6R-stereoisomer). ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:23925

    • Compound Source:

      (+)-5-epi-aristolochene + 2 NADPH + 2 H+ + 2 oxygen -> capsidiol + 2 NADP+ + 2 H2O PlantCyc CPD-4664
      Capsicum annuum PlantCyc CPD-4664
      capsidiol biosynthesis PlantCyc CPD-4664
      Chenopodium quinoa PlantCyc CPD-4664
      Linum usitatissimum PlantCyc CPD-4664
      Nicotiana tabacum PlantCyc CPD-4664
      Oryza brachyantha PlantCyc CPD-4664
      Panicum virgatum PlantCyc CPD-4664
      Petunia axillaris PlantCyc CPD-4664
      Solanum lycopersicum PlantCyc CPD-4664
      Solanum melongena PlantCyc CPD-4664
      Solanum pennellii PlantCyc CPD-4664
      Solanum tuberosum PlantCyc CPD-4664

    • Bio Activity:

      (+)-5-epi-aristolochene + NADPH + oxygen + H+ -> 1-deoxy-capsidiol + NADP+ + H2O PlantCyc CPD-4664
      (+)-5-epi-aristolochene + NADPH + oxygen + H+ -> 3-deoxy-capsidiol + NADP+ + H2O PlantCyc CPD-4664
      (2E,6E)-farnesyl diphosphate -> (+)-5-epi-aristolochene + diphosphate PlantCyc CPD-4664

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module, version: 14.00

Density: 0.9±0.1 g/cm3
Boiling Point: 274.2±20.0 °C at 760 mmHg
Vapour Pressure: 0.0±0.3 mmHg at 25°C
Enthalpy of Vaporization: 49.2±0.8 kJ/mol
Flash Point: 107.8±16.6 °C
Index of Refraction: 1.495
Molar Refractivity: 66.6±0.4 cm3
#H bond acceptors: 0
#H bond donors: 0
#Freely Rotating Bonds: 1
#Rule of 5 Violations: 1
ACD/LogP: 6.41
ACD/LogD (pH 5.5): 5.91
ACD/BCF (pH 5.5): 18146.40
ACD/KOC (pH 5.5): 38907.13
ACD/LogD (pH 7.4): 5.91
ACD/BCF (pH 7.4): 18146.40
ACD/KOC (pH 7.4): 38907.13
Polar Surface Area: 0 Å2
Polarizability: 26.4±0.5 10-24cm3
Surface Tension: 29.7±5.0 dyne/cm
Molar Volume: 228.5±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) =  6.30

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  253.52  (Adapted Stein & Brown method)
    Melting Pt (deg C):  29.52  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  0.0331  (Modified Grain method)
    Subcooled liquid VP: 0.0363 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):  0.05011
       log Kow used: 6.30 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  0.54268 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   6.90E-001  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.776E-001 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  6.30  (KowWin est)
  Log Kaw used:  1.450  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  4.850
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.4663
   Biowin2 (Non-Linear Model)     :   0.1657
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.5354  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.3995  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.3151
   Biowin6 (MITI Non-Linear Model):   0.1293
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.4786
 Ready Biodegradability Prediction:   NO

 Hydrocarbon Biodegradation (BioHCwin v1.01):
     LOG BioHC Half-Life (days) :   1.9337
     BioHC Half-Life (days)     :  85.8390

 Sorption to aerosols (25 Dec C)[AEROWIN v1.00]:
  Vapor pressure (liquid/subcooled):  4.84 Pa (0.0363 mm Hg)
  Log Koa (Koawin est  ): 4.850
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  6.2E-007 
       Octanol/air (Koa) model:  1.74E-008 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  2.24E-005 
       Mackay model           :  4.96E-005 
       Octanol/air (Koa) model:  1.39E-006 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 151.1774 E-12 cm3/molecule-sec
      Half-Life =     0.071 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.849 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     8.593750 E-17 cm3/molecule-sec
      Half-Life =     0.133 Days (at 7E11 mol/cm3)
      Half-Life =      3.200 Hrs
   Fraction sorbed to airborne particulates (phi): 3.6E-005 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  2.32E+004
      Log Koc:  4.365 

 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 = 4.152 (BCF = 1.42e+004)
       log Kow used: 6.30 (estimated)

 Volatilization from Water:
    Henry LC:  0.69 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River:       1.46  hours
    Half-Life from Model Lake :      135.8  hours   (5.658 days)

 Removal In Wastewater Treatment (recommended maximum 95%):
    Total removal:              99.05  percent
    Total biodegradation:        0.26  percent
    Total sludge adsorption:    63.71  percent
    Total to Air:               35.08  percent
      (using 10000 hr Bio P,A,S)

 Level III Fugacity Model:
           Mass Amount    Half-Life    Emissions
            (percent)        (hr)       (kg/hr)
   Air       0.0374          1.11         1000       
   Water     3.17            900          1000       
   Soil      30.3            1.8e+003     1000       
   Sediment  66.5            8.1e+003     0          
     Persistence Time: 2.08e+003 hr

Click to predict properties on the Chemicalize site


Advertisement