ChemSpider 2D Image | Artemisic acid | C15H22O2

Artemisic acid

  • Molecular FormulaC15H22O2
  • Average mass234.334 Da
  • Monoisotopic mass234.161987 Da
  • ChemSpider ID9097710
  • defined stereocentres - 4 of 4 defined stereocentres


More details:






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

(+)-Artemisinic acid
1-Naphthaleneacetic acid, 1,2,3,4,4a,5,6,8a-octahydro-4,7-dimethyl-α-methylene-, (1R,4R,4aS,8aR)- [ACD/Index Name]
2-[(1R,4R,4aS,8aR)-4,7-Dimethyl-1,2,3,4,4a,5,6,8a-octahydro-1-naphthalenyl]acrylic acid [ACD/IUPAC Name]
2-[(1R,4R,4aS,8aR)-4,7-Dimethyl-1,2,3,4,4a,5,6,8a-octahydro-1-naphthalinyl]acrylsäure [German] [ACD/IUPAC Name]
80286-58-4 [RN]
Acide 2-[(1R,4R,4aS,8aR)-4,7-diméthyl-1,2,3,4,4a,5,6,8a-octahydro-1-naphtalényl]acrylique [French] [ACD/IUPAC Name]
Artemisic acid
Artemisinic acid
L66 BUTJ C1 G1 JYVQU1 &&stereoisomer [WLN]
[80286-58-4]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

53N99527G7 [DBID]
CHEBI:63749 [DBID]
nchembio875-comp6 [DBID]
UNII:53N99527G7 [DBID]
UNII-53N99527G7 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Chemical Class:

      A monocarboxylic acid that is prop-2-enoic 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<st ereo>S</stereo>,8a<stereo>R</stereo> diastereoisomer). It is a sesquiterpenoid precursor of artemisinin, obtained from sweet wormwood, <ital>Artemisia annua</ital>. ChEBI CHEBI:63749
      A monocarboxylic acid that is prop-2-enoic 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 sesqu iterpenoid precursor of artemisinin, obtained from sweet wormwood, Artemisia annua. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:63749

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

Density: 1.0±0.1 g/cm3
Boiling Point: 373.6±11.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.8 mmHg at 25°C
Enthalpy of Vaporization: 68.2±6.0 kJ/mol
Flash Point: 273.3±10.2 °C
Index of Refraction: 1.505
Molar Refractivity: 68.1±0.3 cm3
#H bond acceptors: 2
#H bond donors: 1
#Freely Rotating Bonds: 2
#Rule of 5 Violations: 1
ACD/LogP: 5.11
ACD/LogD (pH 5.5): 3.58
ACD/BCF (pH 5.5): 159.99
ACD/KOC (pH 5.5): 598.38
ACD/LogD (pH 7.4): 1.79
ACD/BCF (pH 7.4): 2.60
ACD/KOC (pH 7.4): 9.71
Polar Surface Area: 37 Å2
Polarizability: 27.0±0.5 10-24cm3
Surface Tension: 34.0±3.0 dyne/cm
Molar Volume: 229.9±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) =  5.03

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  345.20  (Adapted Stein & Brown method)
    Melting Pt (deg C):  110.98  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.45E-005  (Modified Grain method)
    Subcooled liquid VP: 0.000171 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):  3.631
       log Kow used: 5.03 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  2.698 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 :   2.06E-006  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  2.081E-006 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  5.03  (KowWin est)
  Log Kaw used:  -4.075  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  9.105
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.7087
   Biowin2 (Non-Linear Model)     :   0.5803
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   3.0459  (weeks       )
   Biowin4 (Primary Survey Model) :   3.8952  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.3442
   Biowin6 (MITI Non-Linear Model):   0.0723
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.3209
 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):  0.0228 Pa (0.000171 mm Hg)
  Log Koa (Koawin est  ): 9.105
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.000132 
       Octanol/air (Koa) model:  0.000313 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.00473 
       Mackay model           :  0.0104 
       Octanol/air (Koa) model:  0.0244 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 123.5164 E-12 cm3/molecule-sec
      Half-Life =     0.087 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.039 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    44.137501 E-17 cm3/molecule-sec
      Half-Life =     0.026 Days (at 7E11 mol/cm3)
      Half-Life =     37.389 Min
   Reaction With Nitrate Radicals May Be Important!
   Fraction sorbed to airborne particulates (phi): 0.00757 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  1341
      Log Koc:  3.128 

 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 = 0.750 (BCF = 5.623)
       log Kow used: 5.03 (estimated)

 Volatilization from Water:
    Henry LC:  2.06E-006 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River:      436.6  hours   (18.19 days)
    Half-Life from Model Lake :       4892  hours   (203.8 days)

 Removal In Wastewater Treatment:
    Total removal:              78.64  percent
    Total biodegradation:        0.68  percent
    Total sludge adsorption:    77.94  percent
    Total to Air:                0.02  percent
      (using 10000 hr Bio P,A,S)

 Level III Fugacity Model:
           Mass Amount    Half-Life    Emissions
            (percent)        (hr)       (kg/hr)
   Air       0.04            0.479        1000       
   Water     17.9            360          1000       
   Soil      60.2            720          1000       
   Sediment  21.9            3.24e+003    0          
     Persistence Time: 576 hr




                    

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