ChemSpider 2D Image | Arteannuic alcohol | C15H24O

Arteannuic alcohol

  • Molecular FormulaC15H24O
  • Average mass220.350 Da
  • Monoisotopic mass220.182709 Da
  • ChemSpider ID13115338

  • defined stereocentres - 4 of 4 defined stereocentres

More details:

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

(+)-artemisinic alcohol
125184-95-4 [RN]
1-Naphthaleneethanol, 1,2,3,4,4a,5,6,8a-octahydro-4,7-dimethyl-β-methylene-, (1R,4R,4aS,8aR)- [ACD/Index Name]
2-[(1R,4R,4aS,8aR)-4,7-Diméthyl-1,2,3,4,4a,5,6,8a-octahydro-1-naphtalényl]-2-propén-1-ol [French] [ACD/IUPAC Name]
2-[(1R,4R,4aS,8aR)-4,7-Dimethyl-1,2,3,4,4a,5,6,8a-octahydro-1-naphthalenyl]-2-propen-1-ol [ACD/IUPAC Name]
2-[(1R,4R,4aS,8aR)-4,7-Dimethyl-1,2,3,4,4a,5,6,8a-octahydro-1-naphthalinyl]-2-propen-1-ol [German] [ACD/IUPAC Name]
Arteannuic alcohol
2-[(1R,4R,4aS,8aR)-4,7-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl]prop-2-en-1-ol
amorpha-4,11-diene-12-ol
artemisinic alcohol
  • Miscellaneous

    • Chemical Class:

      A monocarboxylic acid that is prop-2-en-1-ol acid which is substituted at position 2 by a 4,7-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl group (the 1<stereo>S</stereo>,4<stereo>R</stereo>,4a< stereo>S</stereo>,8a<stereo>R</stereo> diastereoisomer). It is a sesquiterpenoid precursor of artemisinin, obtained from sweet wormwood, <ital>Artemisia annua</ital>. ChEBI CHEBI:64783
      A monocarboxylic acid that is prop-2-en-1-ol acid which is substituted at position 2 by a 4,7-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl group (the 1S,4R,4aS,8aR diastereoisomer). It is a ses quiterpenoid precursor of artemisinin, obtained from sweet wormwood, Artemisia annua. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:64783, CHEBI:64783

    • Compound Source:

      artemisinin biosynthesis PlantCyc CPD-7556
      Linum usitatissimum PlantCyc CPD-7556

    • Bio Activity:

      (+)-amorpha-4,11-diene + NADPH + H+ + oxygen -> artemisinic alcohol + NADP+ + H2O PlantCyc CPD-7556
      artemisinic alcohol + NADPH + oxygen + H+ -> artemisinic aldehyde + NADP+ + 2 H2O PlantCyc CPD-7556

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

Density: 0.9±0.1 g/cm3
Boiling Point: 324.8±11.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.6 mmHg at 25°C
Enthalpy of Vaporization: 65.7±6.0 kJ/mol
Flash Point: 123.5±15.6 °C
Index of Refraction: 1.497
Molar Refractivity: 68.1±0.3 cm3
#H bond acceptors: 1
#H bond donors: 1
#Freely Rotating Bonds: 2
#Rule of 5 Violations: 0
ACD/LogP: 4.97
ACD/LogD (pH 5.5): 4.67
ACD/BCF (pH 5.5): 2072.73
ACD/KOC (pH 5.5): 8233.39
ACD/LogD (pH 7.4): 4.67
ACD/BCF (pH 7.4): 2072.73
ACD/KOC (pH 7.4): 8233.39
Polar Surface Area: 20 Å2
Polarizability: 27.0±0.5 10-24cm3
Surface Tension: 31.2±3.0 dyne/cm
Molar Volume: 232.7±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) =  4.80

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  315.30  (Adapted Stein & Brown method)
    Melting Pt (deg C):  63.90  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.18E-005  (Modified Grain method)
    Subcooled liquid VP: 5.04E-005 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):  8.806
       log Kow used: 4.80 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  10.091 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Vinyl/Allyl Alcohols

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.52E-005  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  7.178E-007 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  4.80  (KowWin est)
  Log Kaw used:  -2.987  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  7.787
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.8014
   Biowin2 (Non-Linear Model)     :   0.7306
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.8722  (weeks       )
   Biowin4 (Primary Survey Model) :   3.6593  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.4152
   Biowin6 (MITI Non-Linear Model):   0.1359
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.2929
 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):  0.00672 Pa (5.04E-005 mm Hg)
  Log Koa (Koawin est  ): 7.787
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.000446 
       Octanol/air (Koa) model:  1.5E-005 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.0159 
       Mackay model           :  0.0345 
       Octanol/air (Koa) model:  0.0012 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 159.8154 E-12 cm3/molecule-sec
      Half-Life =     0.067 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.803 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    44.200001 E-17 cm3/molecule-sec
      Half-Life =     0.026 Days (at 7E11 mol/cm3)
      Half-Life =     37.336 Min
   Reaction With Nitrate Radicals May Be Important!
   Fraction sorbed to airborne particulates (phi): 0.0252 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  1450
      Log Koc:  3.161 

 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 = 2.997 (BCF = 992.8)
       log Kow used: 4.80 (estimated)

 Volatilization from Water:
    Henry LC:  2.52E-005 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River:         36  hours   (1.5 days)
    Half-Life from Model Lake :      517.2  hours   (21.55 days)

 Removal In Wastewater Treatment:
    Total removal:              70.55  percent
    Total biodegradation:        0.62  percent
    Total sludge adsorption:    69.57  percent
    Total to Air:                0.35  percent
      (using 10000 hr Bio P,A,S)

 Level III Fugacity Model:
           Mass Amount    Half-Life    Emissions
            (percent)        (hr)       (kg/hr)
   Air       0.0439          0.449        1000       
   Water     19.3            360          1000       
   Soil      66.4            720          1000       
   Sediment  14.3            3.24e+003    0          
     Persistence Time: 521 hr

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