ChemSpider 2D Image | Zalcitabine | C9H13N3O3

Zalcitabine

  • Molecular FormulaC9H13N3O3
  • Average mass211.218 Da
  • Monoisotopic mass211.095688 Da
  • ChemSpider ID22498
  • defined stereocentres - 2 of 2 defined stereocentres


More details:



Featured data source



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

1-[(2R,5S)-5-(Hydroxymethyl)tetrahydro-2-furanyl]-4-imino-1,4-dihydro-2-pyrimidinol [German] [ACD/IUPAC Name]
1-[(2R,5S)-5-(Hydroxymethyl)tetrahydro-2-furanyl]-4-imino-1,4-dihydro-2-pyrimidinol [ACD/IUPAC Name]
1-[(2R,5S)-5-(Hydroxyméthyl)tétrahydro-2-furanyl]-4-imino-1,4-dihydro-2-pyrimidinol [French] [ACD/IUPAC Name]
2(1H)-Pyrimidinone, 4-amino-1-[(2R,5S)-tetrahydro-5-(hydroxymethyl)-2-furanyl]- [ACD/Index Name]
2',3'-DIDEOXYCYTIDINE
2-Pyrimidinol, 1,4-dihydro-4-imino-1-[(2R,5S)-tetrahydro-5-(hydroxymethyl)-2-furanyl]- [ACD/Index Name]
3'-Azido-3'-deoxythymidine [ACD/IUPAC Name]
4-Amino-1-[(2R,5S)-5-(hydroxymethyl)tetrahydro-2-furanyl]-2(1H)-pyrimidinon [German] [ACD/IUPAC Name]
4-Amino-1-[(2R,5S)-5-(hydroxymethyl)tetrahydro-2-furanyl]-2(1H)-pyrimidinone [ACD/IUPAC Name]
4-Amino-1-[(2R,5S)-5-(hydroxyméthyl)tétrahydro-2-furanyl]-2(1H)-pyrimidinone [French] [ACD/IUPAC Name]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

36775_FLUKA [DBID]
AIDS000006 [DBID]
AIDS-000006 [DBID]
AIDS000600 [DBID]
AIDS-000600 [DBID]
AIDS000773 [DBID]
AIDS-000773 [DBID]
AIDS000886 [DBID]
AIDS-000886 [DBID]
AIDS005889 [DBID]
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  • Experimental Physico-chemical Properties
  • Predicted Physico-chemical Properties
  • Miscellaneous
    • Safety:

      36/37 Alfa Aesar L10619
      40-62 Alfa Aesar L10619
      H302+H312+H332 W&J PharmaChem, Inc. 201302
      H351-H361 Alfa Aesar L10619
      HARMFUL Alfa Aesar L10619
      J05AF03 Wikidata Q2344582
      P261; P262 Biosynth Q-201941
      P281-P201-P202-P308+P313-P405-P501a Alfa Aesar L10619
      P302+P352+P304+P312+P503+P351+P338+P403+P235+P280+P260 W&J PharmaChem, Inc. 201302
      Warning Alfa Aesar L10619
      WARNING: Irreversible damage risk, protect skin/eyes/lungs. Alfa Aesar L10619
    • Target Organs:

      Reverse Transcriptase inhibitor TargetMol T0110
    • Chemical Class:

      A pyrimidine 2',3'-dideoxyribonucleoside compound having cytosine as the nucleobase. ChEBI CHEBI:10101
    • Drug Status:

      approved BIONET-Key Organics KS-1130
    • Bio Activity:

      Anti-infection MedChem Express HY-17392
      Anti-infection; MedChem Express HY-17392
      DNA Damage/DNA Repair;Microbiology & Virology TargetMol T0110
      HIV MedChem Express HY-17392
      HIV NRTIs MedChem Express HY-17392
      Reverse Transcriptase TargetMol T0110
      Zalcitabine(Dideoxycytidine;ddC; 2',3'-Dideoxycytidine) is a nucleoside analog reverse transcriptase inhibitor (NRTI); Zalcitabine is a potent inhibitor of HIV replication at low concentrations, actin g as a chain-terminator of viral DNA by binding to reverse transcriptase. MedChem Express http://www.medchemexpress.com/Metoclopramide-hydrochloride-hydrate.html
      Zalcitabine(Dideoxycytidine;ddC; 2',3'-Dideoxycytidine) is a nucleoside analog reverse transcriptase inhibitor (NRTI); Zalcitabine is a potent inhibitor of HIV replication at low concentrations, acting as a chain-terminator of viral DNA by binding to reverse transcriptase. MedChem Express HY-17392
      Zalcitabine(Dideoxycytidine;ddC; 2',3'-Dideoxycytidine) is a nucleoside analog reverse transcriptase inhibitor (NRTI); Zalcitabine is a potent inhibitor of HIV replication at low concentrations, acting as a chain-terminator of viral DNA by binding to reverse transcriptase. ;IC50 value:;Target: NRTI; reverse transcriptase;Two human cell lines, WiDr (colon) and MCF-7 (breast) were exposed to ddC at 10 microM concentration for various lengths of time (18, 24, 48 and 72 h). On the WiDr cell line the dual effect of concentration and duration of exposure prior to irradiation was investigated. For MCF-7, ddC induced a significant modification of the dose response only with 24 and 48 h preincubation[1].;It is phosphorylated in T cells and other HIV target cells into its active triphosphate form, ddCTP. This active metabolite works as a substrate for HIV reverse transcriptase, and also by incorporation into the viral DNA, hence terminating the chain elongation due to the missing hydroxyl g MedChem Express HY-17392

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

Density: 1.6±0.1 g/cm3
Boiling Point: 415.0±55.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.2 mmHg at 25°C
Enthalpy of Vaporization: 77.2±6.0 kJ/mol
Flash Point: 204.8±31.5 °C
Index of Refraction: 1.686
Molar Refractivity: 50.9±0.5 cm3
#H bond acceptors: 6
#H bond donors: 3
#Freely Rotating Bonds: 2
#Rule of 5 Violations: 0
ACD/LogP: -1.30
ACD/LogD (pH 5.5): -1.14
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 5.56
ACD/LogD (pH 7.4): -1.12
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 5.87
Polar Surface Area: 88 Å2
Polarizability: 20.2±0.5 10-24cm3
Surface Tension: 67.7±7.0 dyne/cm
Molar Volume: 133.8±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) =  -1.72
    Log Kow (Exper. database match) =  -1.30
       Exper. Ref:  Sangster (1993)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  376.77  (Adapted Stein & Brown method)
    Melting Pt (deg C):  141.77  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  7.91E-009  (Modified Grain method)
    MP  (exp database):  217-218 deg C
    Subcooled liquid VP: 8.82E-007 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):  2.417e+004
       log Kow used: -1.30 (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 :   1.17E-016  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  9.095E-014 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -1.30  (exp database)
  Log Kaw used:  -14.320  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  13.020
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.4584
   Biowin2 (Non-Linear Model)     :   0.0909
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.8837  (weeks       )
   Biowin4 (Primary Survey Model) :   3.6627  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.3725
   Biowin6 (MITI Non-Linear Model):   0.1219
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.4294
 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):  0.000118 Pa (8.82E-007 mm Hg)
  Log Koa (Koawin est  ): 13.020
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.0255 
       Octanol/air (Koa) model:  2.57 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.48 
       Mackay model           :  0.671 
       Octanol/air (Koa) model:  0.995 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 111.4624 E-12 cm3/molecule-sec
      Half-Life =     0.096 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.152 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     0.175000 E-17 cm3/molecule-sec
      Half-Life =     6.549 Days (at 7E11 mol/cm3)
   Fraction sorbed to airborne particulates (phi): 0.575 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  19.82
      Log Koc:  1.297 

 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: -1.30 (expkow database)

 Volatilization from Water:
    Henry LC:  1.17E-016 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 7.273E+012  hours   (3.03E+011 days)
    Half-Life from Model Lake : 7.934E+013  hours   (3.306E+012 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       2.47e-008       2.27         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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