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]
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  • 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      off-white crystalline powder OU Chemical Safety Data (No longer updated) More details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 OU Chemical Safety Data (No longer updated) More details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      IPR-MUS LD50 2500 mg kg-1 OU Chemical Safety Data (No longer updated) More details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 OU Chemical Safety Data (No longer updated) More details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:

      adenine and adenosine salvage II PlantCyc ADENOSINE
      adenine and adenosine salvage VI PlantCyc ADENOSINE
      adenosine nucleotides degradation II PlantCyc ADENOSINE
      Aegilops tauschii PlantCyc ADENOSINE
      Amaranthus hypochondriacus PlantCyc ADENOSINE
      Amborella trichopoda PlantCyc ADENOSINE
      Anacardium occidentale PlantCyc ADENOSINE
      Ananas comosus PlantCyc ADENOSINE
      Aquilegia coerulea PlantCyc ADENOSINE
      Arabidopsis halleri PlantCyc ADENOSINE
      Arabidopsis lyrata PlantCyc ADENOSINE
      Arabidopsis thaliana col PlantCyc ADENOSINE
      Asparagus officinalis PlantCyc ADENOSINE
      Beta vulgaris subsp. vulgaris PlantCyc ADENOSINE
      Boechera stricta PlantCyc ADENOSINE
      Brachypodium distachyon PlantCyc ADENOSINE
      Brassica napus PlantCyc ADENOSINE
      Brassica oleracea var. capitata PlantCyc ADENOSINE
      Brassica oleracea var. oleracea PlantCyc ADENOSINE
      Brassica rapa FPsc PlantCyc ADENOSINE
      Brassica rapa subsp. pekinensis PlantCyc ADENOSINE
      Calotropis gigantea PlantCyc ADENOSINE
      Camptotheca acuminata PlantCyc ADENOSINE
      Cannabis sativa PlantCyc ADENOSINE
      Capsella grandiflora PlantCyc ADENOSINE
      Capsella rubella PlantCyc ADENOSINE
      Capsicum annuum PlantCyc ADENOSINE
      Carica papaya PlantCyc ADENOSINE
      Catharanthus roseus PlantCyc ADENOSINE
      Chenopodium quinoa PlantCyc ADENOSINE
      Chlamydomonas reinhardtii PlantCyc ADENOSINE
      Chromochloris zofingiensis PlantCyc ADENOSINE
      Cicer arietinum PlantCyc ADENOSINE
      Citrus clementina PlantCyc ADENOSINE
      Citrus sinensis PlantCyc ADENOSINE
      Coccomyxa subellipsoidea C-169 PlantCyc ADENOSINE
      Corchorus capsularis PlantCyc ADENOSINE
      Cucumis sativus PlantCyc ADENOSINE
      cytokinins degradation PlantCyc ADENOSINE
      Daucus carota subsp. sativus PlantCyc ADENOSINE
      Dianthus caryophyllus PlantCyc ADENOSINE
      Dioscorea rotundata PlantCyc ADENOSINE
      Eucalyptus grandis PlantCyc ADENOSINE
      Eutrema salsugineum PlantCyc ADENOSINE
      Fragaria vesca subsp. vesca PlantCyc ADENOSINE
      Glycine max PlantCyc ADENOSINE
      Gossypium raimondii PlantCyc ADENOSINE
      Helianthus annuus PlantCyc ADENOSINE
      Hordeum vulgare subsp. vulgare PlantCyc ADENOSINE
      Humulus lupulus var. lupulus PlantCyc ADENOSINE
      Kalanchoe fedtschenkoi PlantCyc ADENOSINE
      Kalanchoe laxiflora PlantCyc ADENOSINE
      Leersia perrieri PlantCyc ADENOSINE
      Linum usitatissimum PlantCyc ADENOSINE
      L-methionine degradation I (to L-homocysteine) PlantCyc ADENOSINE
      Lotus japonicus PlantCyc ADENOSINE
      Malus domestica PlantCyc ADENOSINE
      Manihot esculenta PlantCyc ADENOSINE
      Marchantia polymorpha PlantCyc ADENOSINE
      Medicago truncatula PlantCyc ADENOSINE
      Micromonas commoda RCC299 PlantCyc ADENOSINE
      Micromonas pusilla CCMP1545 PlantCyc ADENOSINE
      Mimulus guttatus PlantCyc ADENOSINE
      Miscanthus sinensis PlantCyc ADENOSINE
      Musa acuminata PlantCyc ADENOSINE
      Nicotiana tabacum PlantCyc ADENOSINE
      Olea europaea var. sylvestris PlantCyc ADENOSINE
      Oropetium thomaeum PlantCyc ADENOSINE
      Oryza brachyantha PlantCyc ADENOSINE
      Oryza glaberrima PlantCyc ADENOSINE
      Oryza punctata PlantCyc ADENOSINE
      Oryza rufipogon PlantCyc ADENOSINE
      Oryza sativa Japonica Group PlantCyc ADENOSINE
      Ostreococcus lucimarinus PlantCyc ADENOSINE
      Panicum hallii PlantCyc ADENOSINE
      Panicum virgatum PlantCyc ADENOSINE
      Petunia axillaris PlantCyc ADENOSINE
      Phaseolus vulgaris PlantCyc ADENOSINE
      Physcomitrella patens PlantCyc ADENOSINE
      Populus trichocarpa PlantCyc ADENOSINE
      Prunus persica PlantCyc ADENOSINE
      Ricinus communis PlantCyc ADENOSINE
      Rosa chinensis PlantCyc ADENOSINE
      Rosa multiflora PlantCyc ADENOSINE
      S-adenosyl-L-methionine cycle II PlantCyc ADENOSINE
      Salvia miltiorrhiza PlantCyc ADENOSINE
      Selaginella moellendorffii PlantCyc ADENOSINE
      Setaria italica PlantCyc ADENOSINE
      Setaria viridis PlantCyc ADENOSINE
      Solanum lycopersicum PlantCyc ADENOSINE
      Solanum melongena PlantCyc ADENOSINE
      Solanum pennellii PlantCyc ADENOSINE
      Solanum tuberosum PlantCyc ADENOSINE
      Sorghum bicolor PlantCyc ADENOSINE
      Sphagnum fallax PlantCyc ADENOSINE
      Spinacia oleracea PlantCyc ADENOSINE
      Spirodela polyrhiza PlantCyc ADENOSINE
      Thellungiella parvula PlantCyc ADENOSINE
      Theobroma cacao PlantCyc ADENOSINE
      Trifolium pratense PlantCyc ADENOSINE
      Triticum aestivum PlantCyc ADENOSINE
      Triticum urartu PlantCyc ADENOSINE
      Vitis vinifera PlantCyc ADENOSINE
      Volvox carteri PlantCyc ADENOSINE
      Widely distributed in nature. One of the four principal nucleosides of nucleic acid Zerenex Molecular [ZBioX-0454]
      widespread in living tissue Microsource [01500107]
      Zea mays subsp. mays PlantCyc ADENOSINE
      Zostera marina PlantCyc ADENOSINE
    • Bio Activity:

      7-TM Receptors Tocris Bioscience 3624
      adenosine + ATP -> AMP + ADP + H+ PlantCyc ADENOSINE
      adenosine + H2O -> D-ribofuranose + adenine PlantCyc ADENOSINE
      adenosine + H2O + H+ -> inosine + ammonium PlantCyc ADENOSINE
      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
      AMP + H2O -> adenosine + phosphate PlantCyc ADENOSINE
      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]
      isopentenyl adenosine + FAD + H2O + H+ -> adenosine + 3-methyl-2-butenal + FADH2 PlantCyc ADENOSINE
      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]
      S-adenosyl-L-homocysteine + H2O <--> L-homocysteine + adenosine PlantCyc ADENOSINE
      S-adenosyl-L-homocysteine + H2O -> L-homocysteine + adenosine PlantCyc ADENOSINE
      trans-zeatin riboside + FAD + H2O + H+ -> adenosine + 3-methyl-4-trans-hydroxy-2-butenal + FADH2 PlantCyc ADENOSINE

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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