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Search term: 17226059 (Found by CSID)
ChemSpider 2D Image | ascr#3 | C15H26O6

ascr#3

  • Molecular FormulaC15H26O6
  • Average mass302.363 Da
  • Monoisotopic mass302.172943 Da
  • ChemSpider ID17226059

  • Double-bond stereo - Double-bond stereo

    defined stereocentres - 5 of 5 defined stereocentres

More details:

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

(2E,8R)-8-[(3,6-Dideoxy-α-L-arabino-hexopyranosyl)oxy]-2-nonenoic acid [ACD/IUPAC Name]
(2E,8R)-8-[(3,6-Didesoxy-α-L-arabino-hexopyranosyl)oxy]-2-nonensäure [German] [ACD/IUPAC Name]
2-Nonenoic acid, 8-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]-, (2E,8R)- [ACD/Index Name]
946524-26-1 [RN]
Acide (2E,8R)-8-[(3,6-didésoxy-α-L-arabino-hexopyranosyl)oxy]-2-nonénoïque [French] [ACD/IUPAC Name]
ascaroside C9
ascr#3
(-)-8R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-2E-nonenoic acid
(-)-8R-(Tetrahydro-3'R,5'R-dihydroxy-6'S-methyl-2H-pyran-2'R-yloxy)-2E-nonenoic acid
(2E,8R)-8-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]non-2-enoic acid
More...

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

NChemBio.2007.3-comp2 [DBID]
  • Miscellaneous

    • Chemical Class:

      An (<locant>omega</locant><minus/>1)-hydroxy fatty acid ascaroside obtained by formal condensation of the alcoholic hydroxy group of (2<stereo>E</stereo>,8<stereo>R</stereo>)-8-hydroxynon-2-enoic acid with ascarylopyranose (the <stereo>alpha</stereo> anomer). It is a major component of the dauer pheromone, used by the nematode <ital>Caenorhabditis elegans</ital> as a population-density signal to p romote entry into an alternate larval stage, the nonfeeding and highly persistent dauer diapause, and also synergises with ascr#2, ascr#4, and ascr#8 in male attraction. ChEBI CHEBI:78821
      An (omega-1)-hydroxy fatty acid ascaroside obtained by formal condensation of the alcoholic hydroxy group of (2E,8R)-8-hydroxynon-2-enoic acid with ascarylopyranose (the alpha anomer). It is a major c omponent of the dauer pheromone, used by the nematode Caenorhabditis elegans as a population-density signal to promote entry into an alternate larval stage, the nonfeeding and highly persistent dauer diapause, and also synergises with ascr#2, ascr#4, and ascr#8 in male attraction. ChEBI CHEBI:78821
      An (omega-1)-hydroxy fatty acid ascaroside obtained by formal condensation of the alcoholic hydroxy group of (2E,8R)-8-hydroxynon-2-enoic acid; with ascarylopyranose (the alpha anomer). It is a major component of the dauer pheromone, used by the nematode Caenorhabditis elegans as a population-density signal to p; romote entry into an alternate larval stage, the nonfeeding and highly persistent da uer diapause, and also synergises with ascr#2, ascr#4, and ascr#8 in male attraction. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:78821

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

Density: 1.2±0.1 g/cm3
Boiling Point: 513.0±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±3.0 mmHg at 25°C
Enthalpy of Vaporization: 90.3±6.0 kJ/mol
Flash Point: 186.2±23.6 °C
Index of Refraction: 1.519
Molar Refractivity: 77.5±0.4 cm3
#H bond acceptors: 6
#H bond donors: 3
#Freely Rotating Bonds: 8
#Rule of 5 Violations: 0
ACD/LogP: 1.53
ACD/LogD (pH 5.5): 0.36
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 16.11
ACD/LogD (pH 7.4): -1.44
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 96 Å2
Polarizability: 30.7±0.5 10-24cm3
Surface Tension: 49.0±5.0 dyne/cm
Molar Volume: 255.3±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) =  2.19

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  445.09  (Adapted Stein & Brown method)
    Melting Pt (deg C):  175.23  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  8.83E-011  (Modified Grain method)
    Subcooled liquid VP: 3.19E-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):  395.5
       log Kow used: 2.19 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  50960 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 :   2.95E-016  atm-m3/mole
   Group Method:   4.15E-020  atm-m3/mole
 Henrys LC [VP/WSol estimate using EPI values]:  8.883E-014 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  2.19  (KowWin est)
  Log Kaw used:  -13.919  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  16.109
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.2990
   Biowin2 (Non-Linear Model)     :   0.0051
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   3.1982  (weeks       )
   Biowin4 (Primary Survey Model) :   4.0365  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.5487
   Biowin6 (MITI Non-Linear Model):   0.1368
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.4436
 Ready Biodegradability Prediction:   YES

Hydrocarbon Biodegradation (BioHCwin v1.01):
    Structure incompatible with current estimation method!

 Sorption to aerosols (25 Dec C)[AEROWIN v1.00]:
  Vapor pressure (liquid/subcooled):  4.25E-007 Pa (3.19E-009 mm Hg)
  Log Koa (Koawin est  ): 16.109
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  7.05 
       Octanol/air (Koa) model:  3.16E+003 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.996 
       Mackay model           :  0.998 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  86.0659 E-12 cm3/molecule-sec [Cis-isomer]
      OVERALL OH Rate Constant =  88.7259 E-12 cm3/molecule-sec [Trans-isomer]
      Half-Life =    1.491 Hrs (12-hr day; 1.5E6 OH/cm3) [Cis-isomer]
      Half-Life =    1.447 Hrs (12-hr day; 1.5E6 OH/cm3) [Trans-isomer]
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     0.568750 E-17 cm3/molecule-sec [Cis-]
      OVERALL Ozone Rate Constant =     1.137500 E-17 cm3/molecule-sec [Trans-]
      Half-Life =     2.015 Days (at 7E11 mol/cm3) [Cis-isomer]
      Half-Life =     1.007 Days (at 7E11 mol/cm3) [Trans-isomer]
   Fraction sorbed to airborne particulates (phi): 0.997 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  10
      Log Koc:  1.000 

 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 = 0.500 (BCF = 3.162)
       log Kow used: 2.19 (estimated)

 Volatilization from Water:
    Henry LC:  2.95E-016 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 3.451E+012  hours   (1.438E+011 days)
    Half-Life from Model Lake : 3.765E+013  hours   (1.569E+012 days)

 Removal In Wastewater Treatment:
    Total removal:               2.46  percent
    Total biodegradation:        0.10  percent
    Total sludge adsorption:     2.37  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       1.84e-006       2.81         1000       
   Water     20.9            360          1000       
   Soil      79              720          1000       
   Sediment  0.0925          3.24e+003    0          
     Persistence Time: 729 hr

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