ChemSpider 2D Image | D-(+)-Cycloserine | C3H6N2O2

D-(+)-Cycloserine

  • Molecular FormulaC3H6N2O2
  • Average mass102.092 Da
  • Monoisotopic mass102.042931 Da
  • ChemSpider ID5998
  • defined stereocentres - 1 of 1 defined stereocentres


More details:



Featured data source



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

D-(+)-Cycloserine
(+)-4-Amino-3-isoxazolidinone
(+)-Cycloserine
(4R)-(+)-Cycloserine
(4R)-4-Amino-1,2-oxazolidin-3-on [German] [ACD/IUPAC Name]
(4R)-4-Amino-1,2-oxazolidin-3-one [ACD/IUPAC Name]
(4R)-4-Amino-1,2-oxazolidin-3-one [French] [ACD/IUPAC Name]
(R)-(+)-4-Amino-3-isoxazolidinone
(R)-(+)-CYCLOSERINE
(R)-Cycloserine
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

95IK5KI84Z [DBID]
DRG 0195 [DBID]
I 1431 [DBID]
K 300 [DBID]
UNII-95IK5KI84Z [DBID]
30020_FLUKA [DBID]
AI3-50153 [DBID]
AIDS007654 [DBID]
AIDS-007654 [DBID]
AIDS032282 [DBID]
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  • Experimental Physico-chemical Properties
  • Predicted Physico-chemical Properties
  • Miscellaneous
    • Safety:

      IRRITANT Matrix Scientific 072929
      J04AB01 Wikidata Q418508
      P261; P262 Biosynth C-9390
    • Chemical Class:

      A 4-amino-1,2-oxazolidin-3-one that has <stereo>R</stereo> configuration. It is an antibiotic produced by <ital>Streptomyces garyphalus</ital> or <ital>S. orchidaceus</ital> and is used as part of a m ulti-drug regimen for the treatment of tuberculosis when resistance to, or toxicity from, primary drugs has developed. An analogue of <stereo>D</stereo>-alanine, it interferes with bacterial cell wall synthesis in the cytoplasm by competitive inhibition of <stereo>L</stereo>-alanine racemase (which forms <stereo>D</stereo>-alanine from <stereo>L</stereo>-alanine) and <stereo>D</stereo>-alanine<em _dash/><stereo>D</stereo>-alanine ligase (which incorporates <stereo>D</stereo>-alanine into the pentapeptide required for peptidoglycan formation and bacterial cell wall synthesis). ChEBI CHEBI:40009, CHEBI:74159
      A zwitterion resulting from the transfer of a proton from the ring nitrogen to the primary amino group of <stereo>D</stereo>-cycloserine. The major species at pH 7.3. ChEBI CHEBI:40009, CHEBI:74159
      amino acid Microsource [01500215]
    • Drug Status:

      approved BIONET-Key Organics HS-0079
    • Compound Source:

      Prod. by Streptomyces garyphalus, Streptomyces orchidaceus, Streptomyces lavendulae and Streptomyces nagasakiensis Zerenex Molecular [ZBioX-0178]
      Streptomyces spp Microsource [01500215]
    • Bio Activity:

      Antibacterial MedChem Express HY-B0030
      Anti-infection MedChem Express HY-B0030
      Anti-infection; MedChem Express HY-B0030
      D-Cycloserine is an analog of the amino acid D-alanine. MedChem Express
      D-Cycloserine is an analog of the amino acid D-alanine.; Target: Antibacterial; D-Cycloserine selectively potentiated the duration of motor cortical excitability enhancements induced by anodal tDCS. MedChem Express HY-B0030
      D-Cycloserine is an analog of the amino acid D-alanine.;Target: AntibacterialD-Cycloserine selectively potentiated the duration of motor cortical excitability enhancements induced by anodal tDCS. D-Cycloserine alone did not modulate excitability [1]. Participants receiving d-cycloserine in addition to exposure therapy reported significantly less social anxiety compared with patients receiving exposure therapy plus placebo. Controlled effect sizes were in the medium to large range [2]. Chronic D-cycloserine significantly reduced nicotine self-administration selectively in rats with low baseline nicotine use, but was ineffective with the rats with higher levels of baseline nicotine self-administration [3]. MedChem Express HY-B0030
      Shows antibiotic activity primarily against mycobacteria; Zerenex Molecular [ZBioX-0178]

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

Density: 1.3±0.1 g/cm3
Boiling Point:
Vapour Pressure:
Enthalpy of Vaporization:
Flash Point:
Index of Refraction: 1.475
Molar Refractivity: 22.5±0.3 cm3
#H bond acceptors: 4
#H bond donors: 3
#Freely Rotating Bonds: 0
#Rule of 5 Violations: 0
ACD/LogP: -1.84
ACD/LogD (pH 5.5): -2.39
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -1.85
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 2.32
Polar Surface Area: 64 Å2
Polarizability: 8.9±0.5 10-24cm3
Surface Tension: 40.9±3.0 dyne/cm
Molar Volume: 79.9±3.0 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

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  281.12  (Adapted Stein & Brown method)
    Melting Pt (deg C):  89.59  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  0.000245  (Modified Grain method)
    MP  (exp database):  155.5 dec deg C
    Subcooled liquid VP: 0.00529 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):  1.655e+005
       log Kow used: -1.72 (estimated)
       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:
       Aliphatic Amines

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   6.49E-012  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.989E-010 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -1.72  (KowWin est)
  Log Kaw used:  -9.576  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  7.856
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.8528
   Biowin2 (Non-Linear Model)     :   0.9352
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.9980  (weeks       )
   Biowin4 (Primary Survey Model) :   3.7437  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.4739
   Biowin6 (MITI Non-Linear Model):   0.3545
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.9328
 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):  0.705 Pa (0.00529 mm Hg)
  Log Koa (Koawin est  ): 7.856
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  4.25E-006 
       Octanol/air (Koa) model:  1.76E-005 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.000154 
       Mackay model           :  0.00034 
       Octanol/air (Koa) model:  0.00141 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  37.5716 E-12 cm3/molecule-sec
      Half-Life =     0.285 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     3.416 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.000247 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  27.88
      Log Koc:  1.445 

 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: -1.72 (estimated)

 Volatilization from Water:
    Henry LC:  6.49E-012 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 9.115E+007  hours   (3.798E+006 days)
    Half-Life from Model Lake : 9.944E+008  hours   (4.143E+007 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       0.000153        6.83         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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