ChemSpider 2D Image | ascr#1 | C13H24O6

ascr#1

  • Molecular FormulaC13H24O6
  • Average mass276.326 Da
  • Monoisotopic mass276.157288 Da
  • ChemSpider ID9646210
  • defined stereocentres - 5 of 5 defined stereocentres


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(6R)-6-[(3,6-Dideoxy-α-L-arabino-hexopyranosyl)oxy]heptanoic acid [ACD/IUPAC Name]
(6R)-6-[(3,6-Didesoxy-α-L-arabino-hexopyranosyl)oxy]heptansäure [German] [ACD/IUPAC Name]
Acide (6R)-6-[(3,6-didésoxy-α-L-arabino-hexopyranosyl)oxy]heptanoïque [French] [ACD/IUPAC Name]
ascr#1
Heptanoic acid, 6-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]-, (6R)- [ACD/Index Name]
(-)-6R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)heptanoic acid
(-)-6R-(3'R,5'R-dihydroxy-6'S-methyltetrahydro-pyran-2'-R-yloxy)heptanoic acid
(-)-6R-(Tetrahydro-3'R,5'R-dihydroxy-6'S-methyl-2H-pyran-2'R-yloxy)heptanoic acid
(-)-daumone
690991-47-0 [RN]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

NChemBio.2007.3-comp3 [DBID]
  • Miscellaneous
    • Chemical Class:

      An (<locant>omega</locant><minus/>1)-hydroxy fatty acid ascaroside obtained by formal condensation of the alcoholic hydroxy group of (6<stereo>R</stereo>)-6-hydroxyheptanoic 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 promote entry into an a lternate larval stage, the nonfeeding and highly persistent dauer diapause. It has also been found in <ital>Pristionchus pacificus</ital> and the sour paste nematode <ital>Panagrellus redivivus</ital> . ChEBI CHEBI:78786
      An (omega-1)-hydroxy fatty acid ascaroside obtained by formal condensation of the alcoholic hydroxy group of (6R)-6-hydroxyheptanoic acid with ascarylopyranose; (the alpha anomer). It is a major comp onent of the dauer pheromone, used by the nematode Caenorhabditis elegans as a population-density signal to promote entry into an a; lternate larval stage, the nonfeeding and highly persistent dauer d iapause. It has also been found in Pristionchus pacificus and the sour paste nematode Panagrellus redivivus; . ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:78786

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

Density: 1.2±0.1 g/cm3
Boiling Point: 479.7±45.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.7 mmHg at 25°C
Enthalpy of Vaporization: 85.8±6.0 kJ/mol
Flash Point: 178.1±22.2 °C
Index of Refraction: 1.507
Molar Refractivity: 68.3±0.4 cm3
#H bond acceptors: 6
#H bond donors: 3
#Freely Rotating Bonds: 7
#Rule of 5 Violations: 0
ACD/LogP: 0.44
ACD/LogD (pH 5.5): -0.59
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 4.79
ACD/LogD (pH 7.4): -2.38
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 96 Å2
Polarizability: 27.1±0.5 10-24cm3
Surface Tension: 49.2±5.0 dyne/cm
Molar Volume: 229.5±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) =  1.43

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  418.30  (Adapted Stein & Brown method)
    Melting Pt (deg C):  159.23  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  9.04E-010  (Modified Grain method)
    Subcooled liquid VP: 2.15E-008 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):  2528
       log Kow used: 1.43 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1e+006 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 :   3.58E-016  atm-m3/mole
   Group Method:   8.88E-020  atm-m3/mole
 Henrys LC [VP/WSol estimate using EPI values]:  1.300E-013 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  1.43  (KowWin est)
  Log Kaw used:  -13.835  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  15.265
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.3114
   Biowin2 (Non-Linear Model)     :   0.0074
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   3.2557  (days-weeks  )
   Biowin4 (Primary Survey Model) :   4.0740  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.6137
   Biowin6 (MITI Non-Linear Model):   0.2410
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.5906
 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):  2.87E-006 Pa (2.15E-008 mm Hg)
  Log Koa (Koawin est  ): 15.265
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  1.05 
       Octanol/air (Koa) model:  452 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.974 
       Mackay model           :  0.988 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  66.0387 E-12 cm3/molecule-sec
      Half-Life =     0.162 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.944 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.981 (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: 1.43 (estimated)

 Volatilization from Water:
    Henry LC:  3.58E-016 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 2.719E+012  hours   (1.133E+011 days)
    Half-Life from Model Lake : 2.966E+013  hours   (1.236E+012 days)

 Removal In Wastewater Treatment:
    Total removal:               1.95  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.86  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       5.62e-007       3.89         1000       
   Water     27.7            208          1000       
   Soil      72.2            416          1000       
   Sediment  0.0594          1.87e+003    0          
     Persistence Time: 416 hr




                    

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