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ChemSpider 2D Image | (S)-(-)-Cotinine | C10H12N2O

(S)-(-)-Cotinine

  • Molecular FormulaC10H12N2O
  • Average mass176.215 Da
  • Monoisotopic mass176.094955 Da
  • ChemSpider ID746405
  • defined stereocentres - 1 of 1 defined stereocentres


More details:



Featured data source



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

(S)-(-)-Cotinine
(-)-Cotinine
(−)-Cotinine
(-)-Cotinine solution
(5S)-1-Methyl-5-(3-pyridinyl)-2-pyrrolidinon [German] [ACD/IUPAC Name]
(5S)-1-Methyl-5-(3-pyridinyl)-2-pyrrolidinone [ACD/IUPAC Name]
(5S)-1-Méthyl-5-(3-pyridinyl)-2-pyrrolidinone [French] [ACD/IUPAC Name]
(5S)-1-Methyl-5-(pyridin-3-yl)pyrrolidin-2-on
(S)-1-Methyl-5-(3-pyridinyl)-2-pyrrolidinone
(S)-1-Methyl-5-(3-pyridyl)-2-pyrrolidinone
More...

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

K5161X06LL [DBID]
NIH 10498 [DBID]
27699_FLUKA [DBID]
bmse000577 [DBID]
BRN 0083099 [DBID]
C0430_SIGMA [DBID]
C5923_SIGMA [DBID]
CCRIS 7625 [DBID]
DivK1c_000861 [DBID]
EU-0100285 [DBID]
More...
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      22-36/37/38 Alfa Aesar L11873
      26-36/37 Alfa Aesar L11873
      H302-H315-H319-H335 Alfa Aesar L11873
      Harmful/Irritant SynQuest 4H48-1-S1
      IRRITANT Matrix Scientific 067229
      P261-P280-P305+P351+P338-P304+P340-P405-P501a Alfa Aesar L11873
      R20/21/22,R36/37/38 SynQuest 4H48-1-S1
      S22,S24/25,S26,S36/37/39,S45 SynQuest 4H48-1-S1
      Warning Alfa Aesar L11873
    • Chemical Class:

      alkaloid Microsource [01500208]
      An <element>N</element>-alkylpyrrolidine that consists of <element>N</element>-methylpyrrolidinone bearing a pyridin-3-yl substituent at position C-5 (the 5<stereo>S</stereo>-enantiomer). It is an alk aloid commonly found in <ital>Nicotiana tabacum</ital>. ChEBI CHEBI:68641
    • Drug Status:

      experimental Microsource [01500208]
    • Compound Source:

      Alkaloid from leaf tobacco (Nicotiana tabacum), also detected in Duboisia hopwoodii (Solanaceae) Zerenex Molecular [ZBioX-0171]
      Nicotiana tabacum Microsource [01500208]
    • Bio Activity:

      Acetylcholine (Nicotinic) Receptors Tocris Bioscience 3110
      Cotinine is an alkaloid found in tobacco and is also the predominant metabolite of nicotine, used as a biomarker for exposure to tobacco smoke. MedChem Express http://www.medchemexpress.com/Dipyrocetyl.html, HY-B1178
      Ion Channels Tocris Bioscience 3110
      Ligand-gated Ion Channels Tocris Bioscience 3110
      Major metabolite of nicotine Tocris Bioscience 3110
      Major metabolite of nicotine. Shown to activate a subpopulation of ?3/?6?2 nAChRs in monkey striatum. Displays cognition-enhancing effects in vivo; reduces amyloid ? (A?) aggregation and improves memo ry in an Alzheimer's disease mouse model. Tocris Bioscience 3110
      Major metabolite of nicotine. Shown to activate a subpopulation of ?3/?6?2 nAChRs in monkey striatum. Displays cognition-enhancing effects in vivo; reduces amyloid ? (A?) aggregation and improves memory in an Alzheimer's disease mouse model. Tocris Bioscience 3110
      Major metabolite of nicotine. Shown to activate a subpopulation of alpha3/alpha6beta2 nAChRs in monkey striatum. Displays cognition-enhancing effects in vivo; reduces amyloid beta (Abeta) aggregation and improves memory in an Alzheimer's disease mouse model. Tocris Bioscience 3110
      Others MedChem Express HY-B1178
      Psychostimulant; Zerenex Molecular [ZBioX-0171]

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

Density: 1.1±0.1 g/cm3
Boiling Point: 316.0±0.0 °C at 760 mmHg
Vapour Pressure: 0.0±0.6 mmHg at 25°C
Enthalpy of Vaporization: 55.7±3.0 kJ/mol
Flash Point: 166.7±25.9 °C
Index of Refraction: 1.556
Molar Refractivity: 49.4±0.3 cm3
#H bond acceptors: 3
#H bond donors: 0
#Freely Rotating Bonds: 1
#Rule of 5 Violations: 0
ACD/LogP: -0.23
ACD/LogD (pH 5.5): 0.10
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 25.22
ACD/LogD (pH 7.4): 0.17
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 29.37
Polar Surface Area: 33 Å2
Polarizability: 19.6±0.5 10-24cm3
Surface Tension: 45.7±3.0 dyne/cm
Molar Volume: 153.7±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) =  0.34
    Log Kow (Exper. database match) =  0.07
       Exper. Ref:  Li,NY & Gorrod,JW (1992)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  324.28  (Adapted Stein & Brown method)
    Melting Pt (deg C):  106.15  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  0.000381  (Modified Grain method)
    MP  (exp database):  41 deg C
    BP  (exp database):  250 @ 150 mm Hg deg C
    Subcooled liquid VP: 0.000533 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):  4.891e+004
       log Kow used: 0.07 (expkow database)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  5.5929e+005 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Neutral Organics

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   3.33E-012  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.806E-009 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  0.07  (exp database)
  Log Kaw used:  -9.866  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  9.936
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.7192
   Biowin2 (Non-Linear Model)     :   0.8263
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.5414  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.7802  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.3440
   Biowin6 (MITI Non-Linear Model):   0.2890
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.2410
 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):  0.0711 Pa (0.000533 mm Hg)
  Log Koa (Koawin est  ): 9.936
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  4.22E-005 
       Octanol/air (Koa) model:  0.00212 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.00152 
       Mackay model           :  0.00337 
       Octanol/air (Koa) model:  0.145 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  26.1157 E-12 cm3/molecule-sec
      Half-Life =     0.410 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     4.915 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.00244 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  807.5
      Log Koc:  2.907 

 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: 0.07 (expkow database)

 Volatilization from Water:
    Henry LC:  3.33E-012 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 2.334E+008  hours   (9.725E+006 days)
    Half-Life from Model Lake : 2.546E+009  hours   (1.061E+008 days)

 Removal In Wastewater Treatment:
    Total removal:               1.85  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.76  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       4.62e-005       9.83         1000       
   Water     45.7            900          1000       
   Soil      54.3            1.8e+003     1000       
   Sediment  0.0886          8.1e+003     0          
     Persistence Time: 983 hr




                    

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