ChemSpider 2D Image | Azacitidine | C8H12N4O5

Azacitidine

  • Molecular FormulaC8H12N4O5
  • Average mass244.205 Da
  • Monoisotopic mass244.080765 Da
  • ChemSpider ID9072
  • defined stereocentres - 4 of 4 defined stereocentres


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

1,3,5-triazin-2(1H)-one, 4-amino-1-b-D-ribofuranosyl-
1,3,5-Triazin-2(1H)-one, 4-amino-1-β-D-ribofuranosyl- [ACD/Index Name]
206-280-2 [EINECS]
320-67-2 [RN]
4-amino-1-(b-D-ribofuranosyl)-1,3,5-triazin-2(1H)-one
4-Amino-1-(β-D-ribofuranosyl)-1,3,5-triazin-2(1H)-on [German] [ACD/IUPAC Name]
4-Amino-1-(β-D-ribofuranosyl)-1,3,5-triazin-2(1H)-one [ACD/IUPAC Name]
4-Amino-1-(β-D-ribofuranosyl)-1,3,5-triazin-2(1H)-one [French] [ACD/IUPAC Name]
4-Amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-1,3,5-triazin-2(1H)-one
4-Amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-1,3,5-triazin-2(1H)-on
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

M801H13NRU [DBID]
A1287_SIGMA [DBID]
A2385_SIGMA [DBID]
AIDS000615 [DBID]
AIDS-000615 [DBID]
Antibiotic u 18496 [DBID]
BRN 0620461 [DBID]
C11262 [DBID]
CCRIS 60 [DBID]
CHEBI:2038 [DBID]
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  • References
  • Experimental Physico-chemical Properties
  • Predicted Physico-chemical Properties
  • Miscellaneous
    • Toxicity:

      Organic Compound; Amine; Ether; Drug; Antimetabolite, Antineoplastic; Enzyme Inhibitor; Metabolite; Synthetic Compound Toxin, Toxin-Target Database T3D4676
    • Safety:

      Danger Biosynth W-106861
      GHS07; GHS08 Biosynth W-106861
      H302; H350 Biosynth W-106861
      L01BC07 Wikidata Q416451
      P201; P308+P313 Biosynth W-106861
    • Target Organs:

      DNA Methyltransferase inhibitor TargetMol T1339
    • Chemical Class:

      A <element>N</element>-glycosyl-1,3,5-triazine that is 4-amino-1,3,5-triazin-2(1<element>H</element>)-one substituted by a <stereo>beta</stereo>-<stereo>D</stereo>-ribofuranosyl residue via a <elemen t>N</element>-glycosidic linkage. An antineoplastic agent, it is used in the treatment of myeloid leukaemia. ChEBI CHEBI:2038
    • Compound Source:

      synthetic; U-18496; NSC-102816 Microsource [01502111]
    • Bio Activity:

      5-Azacitidine(5-AzaC) is a nucleoside analogue of cytidine that specifically inhibits DNA methylation by trapping DNA methyltransferases.; IC50 Value: Azacitidine inhibits the L1210 cells growth with IC50 and of 0.019 ?g/mL.; Target: DNMT; in vitro: Azacitidine is widely used to demonstrate the correlation between loss of methylation in specifc gene regions and activation of the associated genes. MedChem Express HY-10586
      Biochemicals & small molecules/Antagonists & inhibitors Hello Bio [HB1374]
      Cell Cycle/DNA Damage MedChem Express HY-10586
      Cell Cycle/DNA Damage; MedChem Express HY-10586
      Cell process/Stem cells/Dedifferentiation Hello Bio [HB1374]
      Cell process/Stem cells/Differentiation Hello Bio [HB1374]
      Chromatin/Epigenetic TargetMol T1339
      DNA Methyltransferase TargetMol T1339
      DNA methyltransferase inhibitor Tocris Bioscience 3842
      DNA methyltransferase inhibitor. Causes hypomethylation. Inhibits Wnt-&beta;-catenin signaling pathway and improves stem cell reprogramming efficiency. Shows anti-viral, anti-proliferative and anti-cancer actions. Hello Bio [HB1374]
      DNA methyltransferase inhibitor. Improves stem cell reprogramming efficiency. Hello Bio [HB1374]
      DNA methyltransferase inhibitor. Incorporates into DNA forming covalent adducts with cellular DNMT1, depleting enzyme activity. Induces demethylation and reactivation of silenced genes. Improves the e fficiency of reprogramming of stem cells; induces differentiation of mesenchymal stem cells into cardiomyocytes. Tocris Bioscience 3842
      DNA methyltransferase inhibitor. Incorporates into DNA forming covalent adducts with cellular DNMT1, depleting enzyme activity. Induces demethylation and reactivation of silenced genes. Improves the efficiency of reprogramming of stem cells; induces differentiation of mesenchymal stem cells into cardiomyocytes. Tocris Bioscience 3842
      DNA Methyltransferases Tocris Bioscience 3842
      Enzymes Tocris Bioscience 3842
      Enzymes/Transferase/DNA methyltransferase (DNMT) Hello Bio [HB1374]
      Nucleoside antimetabolite/analog MedChem Express HY-10586
      Transferases Tocris Bioscience 3842

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

Density: 2.1±0.1 g/cm3
Boiling Point: 534.5±60.0 °C at 760 mmHg
Vapour Pressure: 0.0±3.2 mmHg at 25°C
Enthalpy of Vaporization: 93.2±6.0 kJ/mol
Flash Point: 277.0±32.9 °C
Index of Refraction: 1.823
Molar Refractivity: 51.1±0.5 cm3
#H bond acceptors: 9
#H bond donors: 5
#Freely Rotating Bonds: 2
#Rule of 5 Violations: 1
ACD/LogP: -1.99
ACD/LogD (pH 5.5): -2.31
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.32
ACD/LogD (pH 7.4): -2.30
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.33
Polar Surface Area: 141 Å2
Polarizability: 20.3±0.5 10-24cm3
Surface Tension: 106.8±7.0 dyne/cm
Molar Volume: 117.1±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) =  -3.83
    Log Kow (Exper. database match) =  -2.17
       Exper. Ref:  Sangster (1994)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  456.88  (Adapted Stein & Brown method)
    Melting Pt (deg C):  192.45  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  4.09E-012  (Modified Grain method)
    MP  (exp database):  220 dec deg C
    Subcooled liquid VP: 4.95E-010 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):  8.894e+004
       log Kow used: -2.17 (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:
       Neutral Organics

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   3.76E-021  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.478E-017 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -2.17  (exp database)
  Log Kaw used:  -18.813  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  16.643
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.7601
   Biowin2 (Non-Linear Model)     :   0.3693
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   3.1307  (weeks       )
   Biowin4 (Primary Survey Model) :   3.8740  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.5821
   Biowin6 (MITI Non-Linear Model):   0.1374
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  1.2004
 Ready Biodegradability Prediction:   YES

Hydrocarbon Biodegradation (BioHCwin v1.01):
    Structure incompatible with current estimation method!

 Sorption to aerosols (25 Dec C)[AEROWIN v1.00]:
  Vapor pressure (liquid/subcooled):  6.6E-008 Pa (4.95E-010 mm Hg)
  Log Koa (Koawin est  ): 16.643
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  45.5 
       Octanol/air (Koa) model:  1.08E+004 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.999 
       Mackay model           :  1 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  97.1966 E-12 cm3/molecule-sec
      Half-Life =     0.110 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.321 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: -2.17 (expkow database)

 Volatilization from Water:
    Henry LC:  3.76E-021 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 2.433E+017  hours   (1.014E+016 days)
    Half-Life from Model Lake : 2.655E+018  hours   (1.106E+017 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       4.31e-010       2.64         1000       
   Water     39              360          1000       
   Soil      60.9            720          1000       
   Sediment  0.0713          3.24e+003    0          
     Persistence Time: 579 hr




                    

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