PLANNED MAINTENANCE

There will be scheduled maintenance work beginning on Wednesday 26th February 2020 from 11:00 AM through to 12.00 PM (GMT).

During this time, you may not be able to log into ChemSpider. We apologise for any inconvenience this might cause and thank you for your patience.


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)-4-Amino-3-isoxazolidone
More...

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

95IK5KI84Z [DBID]
DRG 0195 [DBID]
I 1431 [DBID]
K 300 [DBID]
MFCD00005353 [DBID]
UNII-95IK5KI84Z [DBID]
30020_FLUKA [DBID]
AI3-50153 [DBID]
AIDS007654 [DBID]
AIDS-007654 [DBID]
More...
  • 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 4-amino-1,2-oxazolidin-3-one that has R configuration. It is an antibiotic produced by Streptomyces garyphalus or S. orchidaceus and is used as part of a m; ulti-drug regimen for the treatment of tu berculosis when resistance to, or toxicity from, primary drugs has developed. An analogue of D-alanine, it interferes with bacterial cell wall; synthesis in the cytoplasm by competitive inhibition of L-alanine racemase (which forms D-alanine from L-alanine) and D-alanine<em; _dash/>D-alanine ligase (which incorporates D-alanine into the pentapeptide required for peptidoglycan formation and bacte rial cell wall synthesis). ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:40009
      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
      A zwitterion resulting from the transfer of a proton from the ring nitrogen to the primary amino group of D-cycloserine. The major species at pH 7.3. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:74159
      amino acid Microsource [01500215]
    • 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




                    

Click to predict properties on the Chemicalize site






Advertisement