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ChemSpider 2D Image | Adenosine | C10H13N5O4

Adenosine

  • Molecular FormulaC10H13N5O4
  • Average mass267.241 Da
  • Monoisotopic mass267.096741 Da
  • ChemSpider ID54923
  • defined stereocentres - 4 of 4 defined stereocentres


More details:



Featured data source



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

Adenosine [BAN] [ACD/Index Name] [ACD/IUPAC Name] [USAN] [Wiki]
(-)-adenosine
(–)-adenosine
(2R,3R,4S,5R)-2-(6-Amino-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydro-3,4-furandiol
(2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol
(2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-(hydroxyméthyl)tétrahydrofurane-3,4-diol [French]
1-(6-amino-9H-purin-9-yl)-1-deoxy-β-D-Ribofuranose
1-C-(7-Amino-1H-pyrazolo[4,3-d]pyrimidin-3-yl)-1,4-anhydro-(1S)-D-Ribitol
200-389-9 [EINECS]
4-26-00-03598 [Beilstein]
More...

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

CHEBI:16335 [DBID]
NSC 102811 [DBID]
A4036_SIGMA [DBID]
A9251_SIGMA [DBID]
AI3-52413 [DBID]
AIDS001224 [DBID]
AIDS-001224 [DBID]
Bio1_000437 [DBID]
Bio1_000926 [DBID]
Bio1_001415 [DBID]
More...
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Appearance:

      off-white crystalline powder OU Chemical Safety Data (No longer updated) More details
    • Stability:

      Stable. Incompatible with strong oxidizing agents. OU Chemical Safety Data (No longer updated) More details
    • Toxicity:

      IPR-MUS LD50 2500 mg kg-1 OU Chemical Safety Data (No longer updated) More details
      Organic Compound; Amine; Ether; Drug; Food Toxin; Anti-Arrhythmia Agent; Analgesic; Cardiovascular Agent; Vasodilator Agent; Metabolite; Animal Toxin; Natural Compound Toxin, Toxin-Target Database T3D4275
    • Safety:

      C01EB10 Wikidata Q190012
      Minimize exposure. OU Chemical Safety Data (No longer updated) More details
      P261; P262 Biosynth Q-200598
    • Chemical Class:

      A ribonucleoside composed of a molecule of adenine attached to a ribofuranose moiety via a <stereo>beta</stereo><bond>1</bond>N<smallsup>9</smallsup>-glycosidic bond. ChEBI CHEBI:16335
      alkaloid Microsource [01500107]
    • Compound Source:

      Widely distributed in nature. One of the four principal nucleosides of nucleic acid Zerenex Molecular [ZBioX-0454]
      widespread in living tissue Microsource [01500107]
    • Bio Activity:

      7-TM Receptors Tocris Bioscience 3624
      Adenosine is a nucleoside composed of a molecule of adenine attached to a ribose sugar molecule (ribofuranose) moiety via a ?-N9-glycosidic bond.; Target: Nucleoside antimetabolite/analog; Adenosine plays an important role in biochemical processes, such as energy transfer ? as adenosine triphosphate (ATP) and adenosine diphosphate (ADP) ? as well as in signal transduction as cyclic adenosine monophosphate, cAMP. MedChem Express HY-B0228
      Adenosine Receptors Tocris Bioscience 3624
      Antiarrhythmic agent; Zerenex Molecular [ZBioX-0454]
      Biochemicals & small molecules/Agonists & activators Hello Bio [HB2843]
      Cell Cycle/DNA Damage MedChem Express HY-B0228
      Cell Cycle/DNA Damage; MedChem Express HY-B0228
      Endogenous adenosine receptor agonist Tocris Bioscience 3624
      Endogenous adenosine receptor agonist Hello Bio [HB2843]
      Endogenous adenosine receptor agonist (EC<sub>50</sub> values are 0.29 0.31, 0.7 and 24 &micro;M at human A<sub>3</sub>, A<sub>1</sub>, A<sub>2A</sub> and A<sub>2B</sub> receptors respectively). Shows neuromodulatory, cytoprotective, anti-inflammatory and cardioprotective actions. Hello Bio [HB2843]
      Neurotransmitter that acts as the preferred endogenous agonist at all adenosine receptor subtypes. Tocris Bioscience 3624
      Non-selective Adenosine Tocris Bioscience 3624
      Nucleoside antimetabolite/analog MedChem Express HY-B0228
      Receptors & Transporters/G protein coupled receptors/Adenosine/Non-selective Hello Bio [HB2843]

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

Density: 2.1±0.1 g/cm3
Boiling Point: 676.3±65.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.2 mmHg at 25°C
Enthalpy of Vaporization: 104.3±3.0 kJ/mol
Flash Point: 362.8±34.3 °C
Index of Refraction: 1.907
Molar Refractivity: 60.0±0.5 cm3
#H bond acceptors: 9
#H bond donors: 5
#Freely Rotating Bonds: 2
#Rule of 5 Violations: 1
ACD/LogP: -1.02
ACD/LogD (pH 5.5): -1.00
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 6.70
ACD/LogD (pH 7.4): -0.99
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 6.94
Polar Surface Area: 140 Å2
Polarizability: 23.8±0.5 10-24cm3
Surface Tension: 107.6±7.0 dyne/cm
Molar Volume: 128.2±7.0 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) =  -1.38
    Log Kow (Exper. database match) =  -1.05
       Exper. Ref:  Hansch,C et al. (1995)
    Log Kow (Exper. database match) =  -1.11
       Exper. Ref:  Pomona (1987)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  537.33  (Adapted Stein & Brown method)
    Melting Pt (deg C):  230.04  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  3.29E-015  (Modified Grain method)
    MP  (exp database):  257-257.5 deg C
    Subcooled liquid VP: 1.12E-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):  8228
       log Kow used: -1.11 (expkow database)
       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:
       Aromatic Amines
       Imidazoles

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.11E-022  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.406E-019 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -1.11  (exp database)
  Log Kaw used:  -20.343  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  19.233
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.5154
   Biowin2 (Non-Linear Model)     :   0.0590
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.9449  (weeks       )
   Biowin4 (Primary Survey Model) :   3.7324  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.3599
   Biowin6 (MITI Non-Linear Model):   0.0336
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.6922
 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):  1.49E-010 Pa (1.12E-012 mm Hg)
  Log Koa (Koawin est  ): 19.233
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  2.01E+004 
       Octanol/air (Koa) model:  4.2E+006 
   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 = 238.3639 E-12 cm3/molecule-sec
      Half-Life =     0.045 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.538 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   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    :  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: -1.11 (expkow database)

 Volatilization from Water:
    Henry LC:  1.11E-022 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 8.623E+018  hours   (3.593E+017 days)
    Half-Life from Model Lake : 9.407E+019  hours   (3.919E+018 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       6.71e-009       1.08         1000       
   Water     39              360          1000       
   Soil      61              720          1000       
   Sediment  0.0713          3.24e+003    0          
     Persistence Time: 579 hr




                    

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