ChemSpider 2D Image | Cabergoline | C26H37N5O2

Cabergoline

  • Molecular FormulaC26H37N5O2
  • Average mass451.604 Da
  • Monoisotopic mass451.294739 Da
  • ChemSpider ID49452
  • defined stereocentres - 3 of 3 defined stereocentres


More details:



Featured data source



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

(6aR,9R,10aR)-N-[3-(Dimethylamino)propyl]-N-(ethylcarbamoyl)-7-prop-2-en-1-yl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]chinolin-9-carboxamid
(6aR,9R,10aR)-N-[3-(diméthylamino)propyl]-N-(éthylcarbamoyl)-7-prop-2-én-1-yl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoléine-9-carboxamide
(6aR,9R,10aR)-N-[3-(dimethylamino)propyl]-N-(ethylcarbamoyl)-7-prop-2-en-1-yl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide
(8b)-N-[3-(Dimethylamino)propyl]-N-[(ethylamino)carbonyl]-6-(2-propenyl)ergoline-8-carboxamide
(8β)-6-Allyl-N-[3-(dimethylamino)propyl]-N-(ethylcarbamoyl)ergolin-8-carboxamid [German] [ACD/IUPAC Name]
(8β)-6-Allyl-N-[3-(dimethylamino)propyl]-N-(ethylcarbamoyl)ergoline-8-carboxamide [ACD/IUPAC Name]
(8β)-6-Allyl-N-[3-(diméthylamino)propyl]-N-(éthylcarbamoyl)ergoline-8-carboxamide [French] [ACD/IUPAC Name]
(8β)-N-[3-(dimethylamino)propyl]-N-(ethylcarbamoyl)-6-(prop-2-en-1-yl)ergoline-8-carboxamide
(8β)-N-[3-(dimethylamino)propyl]-N-(ethylcarbamoyl)-6-prop-2-en-1-ylergoline-8-carboxamide
(8β)-N-[3-(dimethylamino)propyl]-N-[(ethylamino)carbonyl]-6-prop-2-en-1-ylergoline-8-carboxamide
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

BRN 6020775 [DBID]
C08187 [DBID]
CG-101 [DBID]
D00987 [DBID]
FCE 21336 [DBID]
FCE-21336 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      G02CB03 Wikidata Q423308
      N04BC06 Wikidata Q423308
    • Chemical Class:

      An <element>N</element>-acylurea that is (8<stereo>R</stereo>)-ergoline-8-carboxamide in which the hydrogen attached to the piperidine nitrogen (position 6) is substituted by an allyl group and the hy drogens attached to the carboxamide nitrogen are substituted by a 3-(dimethylamino)propyl group and an <element>N</element>-ethylcarbamoyl group. A dopamine D<smallsub>2</smallsub> receptor agonist, c abergoline is used in the management of Parkinson's disease and of disorders associated with hyperprolactinaemia. ChEBI CHEBI:3286
    • Bio Activity:

      dopamine D2-like agonist Tocris Bioscience [2664]

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

Density: 1.2±0.1 g/cm3
Boiling Point:
Vapour Pressure:
Enthalpy of Vaporization:
Flash Point:
Index of Refraction: 1.594
Molar Refractivity: 132.5±0.3 cm3
#H bond acceptors: 7
#H bond donors: 2
#Freely Rotating Bonds: 8
#Rule of 5 Violations: 0
ACD/LogP: 2.43
ACD/LogD (pH 5.5): -0.52
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): 1.49
ACD/BCF (pH 7.4): 2.82
ACD/KOC (pH 7.4): 21.42
Polar Surface Area: 72 Å2
Polarizability: 52.5±0.5 10-24cm3
Surface Tension: 48.6±3.0 dyne/cm
Molar Volume: 390.4±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) =  2.83

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  655.73  (Adapted Stein & Brown method)
    Melting Pt (deg C):  285.34  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  3.29E-015  (Modified Grain method)
    Subcooled liquid VP: 2.52E-012 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):  0.4353
       log Kow used: 2.83 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  0.20544 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.62E-021  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  4.491E-015 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  2.83  (KowWin est)
  Log Kaw used:  -18.970  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  21.800
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.2314
   Biowin2 (Non-Linear Model)     :   0.0012
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.5419  (recalcitrant)
   Biowin4 (Primary Survey Model) :   2.4831  (weeks-months)
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.5024
   Biowin6 (MITI Non-Linear Model):   0.0001
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -2.3890
 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):  3.36E-010 Pa (2.52E-012 mm Hg)
  Log Koa (Koawin est  ): 21.800
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  8.93E+003 
       Octanol/air (Koa) model:  1.55E+009 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  1 
       Mackay model           :  1 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 464.2572 E-12 cm3/molecule-sec
      Half-Life =     0.023 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    16.588 Min
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     1.200000 E-17 cm3/molecule-sec
      Half-Life =     0.955 Days (at 7E11 mol/cm3)
      Half-Life =     22.920 Hrs
   Fraction sorbed to airborne particulates (phi): 1 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  2.352E+006
      Log Koc:  6.371 

 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 = 1.477 (BCF = 29.97)
       log Kow used: 2.83 (estimated)

 Volatilization from Water:
    Henry LC:  2.62E-021 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 4.749E+017  hours   (1.979E+016 days)
    Half-Life from Model Lake : 5.181E+018  hours   (2.159E+017 days)

 Removal In Wastewater Treatment:
    Total removal:               4.48  percent
    Total biodegradation:        0.11  percent
    Total sludge adsorption:     4.37  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       4.38e-009       0.54         1000       
   Water     8.16            4.32e+003    1000       
   Soil      91.7            8.64e+003    1000       
   Sediment  0.151           3.89e+004    0          
     Persistence Time: 5.94e+003 hr




                    

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