ChemSpider 2D Image | Abacavir | C14H18N6O

Abacavir

  • Molecular FormulaC14H18N6O
  • Average mass286.332 Da
  • Monoisotopic mass286.154205 Da
  • ChemSpider ID390063
  • defined stereocentres - 2 of 2 defined stereocentres


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

(1S,4R)-4-[2-Amino-6-(cyclopropylamino)-9H-purin-9-yl]-2-cyclopentene-1-methanol
(1S,cis)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]-2-cyclopentene-1-methanol
{(1S,4R)-4-[2-Amino-6-(cyclopropylamino)-9H-purin-9-yl]-2-cyclopenten-1-yl}methanol [German] [ACD/IUPAC Name]
{(1S,4R)-4-[2-Amino-6-(cyclopropylamino)-9H-purin-9-yl]-2-cyclopenten-1-yl}methanol [ACD/IUPAC Name]
{(1S,4R)-4-[2-Amino-6-(cyclopropylamino)-9H-purin-9-yl]-2-cyclopentén-1-yl}méthanol [French] [ACD/IUPAC Name]
{(1S,4R)-4-[2-Amino-6-(cyclopropylamino)-9H-purin-9-yl]cyclopent-2-en-1-yl}methanol
{(4R)-4-[2-Amino-6-(cyclopropylamino)-9H-purin-9-yl]cyclopent-2-en-1-yl}methanol
136470-78-5 [RN]
2-Cyclopentene-1-methanol, 4-(2-amino-6-(cyclopropylamino)-9H-purin-9-yl)-, (1S,4R)-
2-Cyclopentene-1-methanol, 4-(2-amino-6-(cyclopropylamino)-9H-purin-9-yl)-, (1S-cis)-
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

CHEBI:421707 [DBID]
AIDS008715 [DBID]
AIDS-008715 [DBID]
AIDS028596 [DBID]
AIDS-028596 [DBID]
C07624 [DBID]
CHEBI:2360 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      J05AF06 Wikidata Q304330
    • Target Organs:

      Reverse Transcriptase inhibitor TargetMol T1267
    • Chemical Class:

      (1<stereo>S</stereo>)-Cyclopent-2-en-1-ylmethanol in which the <ital>pro</ital>-<stereo>R</stereo> hydrogen at the 4-position is substituted by a 2-amino-6-(cyclopropylamino)-9<element>H</element>-pur in-9-yl group. A nucleoside analogue reverse transcriptase inhibitor (NRTI) with antiretroviral activity against HIV, it is used (particularly as the sulfate) with other antiretrovirals in combination therapy of HIV infection. ChEBI CHEBI:421707
    • Bio Activity:

      Abacavir is a powerful nucleoside analog reverse transcriptase inhibitor (NRTI) used to treat HIV and AIDS. MedChem Express http://www.medchemexpress.com/iloperidone-hydrochloride.html, HY-17423
      Abacavir is a powerful nucleoside analog reverse transcriptase inhibitor (NRTI) used to treat HIV and AIDS. ;IC50 value:;Target: NRTI; reverse transcriptase inhibitorAbacavir is a nucleoside reverse transcriptase inhibitor marketed since 1999 for the treatment of infection with the human immunodeficiency virus type 1 (HIV). Despite its clinical efficacy, abacavir administration has been associated with serious and sometimes fatal toxic events. Abacavir has been reported to undergo bioactivation in vitro, yielding reactive species that bind covalently to human serum albumin, but the haptenation mechanism and its significance to the toxic events induced by this anti-HIV drug have yet to be elucidated. ;The mechanism underlying abacavir hypersensitivity syndrome is related to the change in the HLA-B*5701 protein product. Abacavir binds with high specificity to the HLA-B*5701 protein, changing the shape and chemistry of the antigen-binding cleft. This results in a change in immunolog MedChem Express HY-17423
      Anti-infection MedChem Express HY-17423
      Anti-infection; MedChem Express HY-17423
      DNA Damage/DNA Repair;Microbiology & Virology TargetMol T1267
      HIV MedChem Express HY-17423
      HIV NRTIs MedChem Express HY-17423
      HIV reverse transcriptase inhibitor Zerenex Molecular [ZBioX-0001]
      HIV-1 reverse-transcriptase TargetMol T1267

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

Density: 1.7±0.1 g/cm3
Boiling Point: 636.0±65.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.0 mmHg at 25°C
Enthalpy of Vaporization: 98.8±3.0 kJ/mol
Flash Point: 338.4±34.3 °C
Index of Refraction: 1.864
Molar Refractivity: 75.8±0.5 cm3
#H bond acceptors: 7
#H bond donors: 4
#Freely Rotating Bonds: 4
#Rule of 5 Violations: 0
ACD/LogP: 0.72
ACD/LogD (pH 5.5): 1.15
ACD/BCF (pH 5.5): 4.01
ACD/KOC (pH 5.5): 84.10
ACD/LogD (pH 7.4): 1.32
ACD/BCF (pH 7.4): 5.91
ACD/KOC (pH 7.4): 123.99
Polar Surface Area: 102 Å2
Polarizability: 30.1±0.5 10-24cm3
Surface Tension: 80.2±7.0 dyne/cm
Molar Volume: 167.7±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) =  1.62

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  521.52  (Adapted Stein & Brown method)
    Melting Pt (deg C):  222.65  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  3.14E-013  (Modified Grain method)
    Subcooled liquid VP: 4.09E-011 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):  608.3
       log Kow used: 1.62 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  41403 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 :   1.87E-016  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.945E-016 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  1.62  (KowWin est)
  Log Kaw used:  -14.117  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  15.737
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.3025
   Biowin2 (Non-Linear Model)     :   0.0229
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.4565  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.3473  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.1274
   Biowin6 (MITI Non-Linear Model):   0.0019
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.0450
 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):  5.45E-009 Pa (4.09E-011 mm Hg)
  Log Koa (Koawin est  ): 15.737
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  550 
       Octanol/air (Koa) model:  1.34E+003 
   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 = 265.4732 E-12 cm3/molecule-sec
      Half-Life =     0.040 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    29.009 Min
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    20.000000 E-17 cm3/molecule-sec
      Half-Life =     0.057 Days (at 7E11 mol/cm3)
      Half-Life =      1.375 Hrs
   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    :  62.76
      Log Koc:  1.798 

 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 = -0.102 (BCF = 0.7908)
       log Kow used: 1.62 (estimated)

 Volatilization from Water:
    Henry LC:  1.87E-016 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 5.298E+012  hours   (2.208E+011 days)
    Half-Life from Model Lake :  5.78E+013  hours   (2.408E+012 days)

 Removal In Wastewater Treatment:
    Total removal:               2.01  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.92  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       6.54e-005       0.568        1000       
   Water     30.5            900          1000       
   Soil      69.4            1.8e+003     1000       
   Sediment  0.0831          8.1e+003     0          
     Persistence Time: 1.24e+003 hr




                    

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