ChemSpider 2D Image | Domoic acid | C15H21NO6

Domoic acid

  • Molecular FormulaC15H21NO6
  • Average mass311.330 Da
  • Monoisotopic mass311.136902 Da
  • ChemSpider ID4445428
  • Double-bond stereo - Double-bond stereo

    defined stereocentres - 4 of 4 defined stereocentres

More details:

Featured data source

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

(3S,4S)-4-[(2Z,4E,6R)-6-Carboxy-2,4-heptadien-2-yl]-3-(carboxymethyl)-L-prolin [German] [ACD/IUPAC Name]
(3S,4S)-4-[(2Z,4E,6R)-6-Carboxy-2,4-heptadien-2-yl]-3-(carboxymethyl)-L-proline [ACD/IUPAC Name]
(3S,4S)-4-[(2Z,4E,6R)-6-Carboxy-2,4-heptadién-2-yl]-3-(carboxyméthyl)-L-proline [French] [ACD/IUPAC Name]
[2S-[2a,3b,4b(1Z,3E,5S*)]]-2-Carboxy-4-(5-carboxy-1-methyl-1,3-hexadienyl)-3-pyrrolidineacetic Acid
14277-97-5 [RN]
Domoic acid
L-Domoic acid
L-Proline, 3-(carboxymethyl)-4-[(1Z,3E,5R)-5-carboxy-1-methyl-1,3-hexadien-1-yl]-, (3S,4S)- [ACD/Index Name]
(2S,3S,4R,5'R)-2-Carboxy-4-(5'-carboxy-1'-methyl-1Z,3Ehexadienyl)-3-pyrrolidineacetic acid

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

BRN 5768789 [DBID]
C13732 [DBID]
HSDB 7242 [DBID]
MLS000517259 [DBID]
NSC 288031 [DBID]
SMR000127427 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Bio Activity:

      Glutamate (Ionotropic) Receptors Tocris Bioscience 269
      Ion Channels Tocris Bioscience 269
      Kainate receptor agonist. More potent and possibly more selective than kainate at kainate receptors, as demonstrated in electrophysiological studies. Tocris Bioscience 0269, 269
      Ligand-gated Ion Channels Tocris Bioscience 269
      Potent, selective kainate agonist Tocris Bioscience 0269

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

Density: 1.3±0.1 g/cm3
Boiling Point: 607.2±55.0 °C at 760 mmHg
Vapour Pressure: 0.0±3.7 mmHg at 25°C
Enthalpy of Vaporization: 98.5±6.0 kJ/mol
Flash Point: 321.0±31.5 °C
Index of Refraction: 1.545
Molar Refractivity: 77.2±0.3 cm3
#H bond acceptors: 7
#H bond donors: 4
#Freely Rotating Bonds: 7
#Rule of 5 Violations: 0
ACD/LogP: 0.61
ACD/LogD (pH 5.5): -3.27
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -3.64
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 124 Å2
Polarizability: 30.6±0.5 10-24cm3
Surface Tension: 53.0±3.0 dyne/cm
Molar Volume: 244.4±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) =  -0.89

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  547.12  (Adapted Stein & Brown method)
    Melting Pt (deg C):  313.83  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  9.82E-013  (Modified Grain method)
    Subcooled liquid VP: 1.73E-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):  515.3
       log Kow used: -0.89 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  203.11 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Aliphatic Amines-acid

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   7.61E-019  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  7.807E-016 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -0.89  (KowWin est)
  Log Kaw used:  -16.507  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  15.617
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.9712
   Biowin2 (Non-Linear Model)     :   0.8357
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   3.6294  (days-weeks  )
   Biowin4 (Primary Survey Model) :   4.5985  (hours-days  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.4379
   Biowin6 (MITI Non-Linear Model):   0.0456
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  1.0525
 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):  2.31E-007 Pa (1.73E-009 mm Hg)
  Log Koa (Koawin est  ): 15.617
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  13 
       Octanol/air (Koa) model:  1.02E+003 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.998 
       Mackay model           :  0.999 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 278.8585 E-12 cm3/molecule-sec
      Half-Life =     0.038 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    27.617 Min
   Ozone Reaction:
      OVERALL Ozone Rate Constant =   100.000000 E-17 cm3/molecule-sec
      Half-Life =     0.011 Days (at 7E11 mol/cm3)
      Half-Life =     16.502 Min
   Reaction With Nitrate Radicals May Be Important!
   Fraction sorbed to airborne particulates (phi): 0.998 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  1.164E+004
      Log Koc:  4.066 

 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: -0.89 (estimated)

 Volatilization from Water:
    Henry LC:  7.61E-019 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.358E+015  hours   (5.656E+013 days)
    Half-Life from Model Lake : 1.481E+016  hours   (6.171E+014 days)

 Removal In Wastewater Treatment:
    Total removal:               1.85  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.75  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       3.42e-008       0.212        1000       
   Water     34.4            208          1000       
   Soil      65.5            416          1000       
   Sediment  0.0596          1.87e+003    0          
     Persistence Time: 387 hr


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