ChemSpider 2D Image | Trimethoprim | C14H18N4O3

Trimethoprim

  • Molecular FormulaC14H18N4O3
  • Average mass290.318 Da
  • Monoisotopic mass290.137878 Da
  • ChemSpider ID5376

More details:



Featured data source



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

1047
2,4-Pyrimidinediamine, 5-[(3,4,5-trimethoxyphenyl)methyl]- [ACD/Index Name]
212-006-2 [EINECS]
5-(3,4,5-Trimethoxybenzyl)-2,4-pyrimidindiamin [German] [ACD/IUPAC Name]
5-(3,4,5-Trimethoxybenzyl)-2,4-pyrimidinediamine [ACD/IUPAC Name]
5-(3,4,5-Triméthoxybenzyl)-2,4-pyrimidinediamine [French] [ACD/IUPAC Name]
5-(3,4,5-Trimethoxybenzyl)pyrimidin-2,4-diamin [German]
5-(3,4,5-trimethoxybenzyl)pyrimidine-2,4-diamine
5-(3,4,5-triméthoxybenzyl)pyrimidine-2,4-diamine [French]
5-{[3,4,5-tris(methyloxy)phenyl]methyl}pyrimidine-2,4-diamine
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

AN164J8Y0X [DBID]
UNII-AN164J8Y0X [DBID]
46984_RIEDEL [DBID]
92131_FLUKA [DBID]
AI3-52594 [DBID]
AIDS010922 [DBID]
AIDS-010922 [DBID]
AIDS110808 [DBID]
AIDS-110808 [DBID]
BRN 0625127 [DBID]
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  • Experimental Physico-chemical Properties
  • Predicted Physico-chemical Properties
  • Miscellaneous
    • Appearance:

      white powder Oxford University Chemical Safety Data (No longer updated) More details
    • Stability:

      Stable. Incompatible with strong oxidizing agents, acids. Oxford University Chemical Safety Data (No longer updated) More details
    • Toxicity:

      ORL-RAT LD50 2800 mg kg-1, ORL-MUS LD50 4850 mg kg-1, IPR-MUS LD50 3500 mg kg-1, IVN-MUS LD50 200 mg kg-1 Oxford University Chemical Safety Data (No longer updated) More details
    • Safety:

      IRRITANT Matrix Scientific 058373
      J01EA01 Wikidata Q422665
      None LKT Labs [T7034]
      Safety glasses, adequate ventilation. Oxford University Chemical Safety Data (No longer updated) More details
      Xi Abblis Chemicals AB1004879
    • Target Organs:

      Antibiotic TargetMol T1153
    • Chemical Class:

      An aminopyrimidine antibiotic whose structure consists of pyrimidine 2,4-diamine and 1,2,3-trimethoxybenzene moieties linked by a methylene bridge. ChEBI CHEBI:45924
    • Drug Status:

      approved BIONET-Key Organics KS-1145
    • Compound Source:

      synthetic Microsource [01500595]
    • Bio Activity:

      Antibacterial agent; Antiseptic; Zerenex Molecular [ZBioX-0607]
      Antifolate MedChem Express HY-B0510
      Cell Cycle/DNA Damage MedChem Express HY-B0510
      Cell Cycle/DNA Damage; MedChem Express HY-B0510
      DHFR;Thymidylate synthase TargetMol T1153
      Microbiology & Virology TargetMol T1153
      Trimethoprim is a bacteriostatic antibiotic used mainly in the prophylaxis and treatment of urinary tract infections. MedChem Express
      Trimethoprim is a bacteriostatic antibiotic used mainly in the prophylaxis and treatment of urinary tract infections.; Target: DHFR; Trimethoprim (TMP), an inhibitor of dihydrofolate reductase, decreases the level of tetrahydrofolate supplying one-carbon units for biosynthesis of nucleotides, proteins, and panthotenate. MedChem Express HY-B0510
      Trimethoprim is a bacteriostatic antibiotic used mainly in the prophylaxis and treatment of urinary tract infections.;Target: DHFR;Trimethoprim (TMP), an inhibitor of dihydrofolate reductase, decreases the level of tetrahydrofolate supplying one-carbon units for biosynthesis of nucleotides, proteins, and panthotenate. TMP caused induction of DnaK, DnaJ, GroEL, ClpB, and IbpA/B Hsps. Among these Hsps, IbpA/B were most efficiently induced by TMP and coaggregated with the insoluble proteins [1]. Trimethoprim binds to dihydrofolate reductase and inhibits the reduction of dihydrofolic acid (DHF) to tetrahydrofolic acid (THF). THF is an essential precursor in the thymidine synthesis pathway and interference with this pathway inhibits bacterial DNA synthesis. Trimethoprim's affinity for bacterial dihydrofolate reductase is several thousand times greater than its affinity for human dihydrofolate reductase. Sulfamethoxazole inhibits dihydropteroate synthetase, an enzyme involved further upst MedChem Express HY-B0510
  • Gas Chromatography
    • Retention Index (Kovats):

      2645 (estimated with error: 89) NIST Spectra mainlib_247707, replib_79715, replib_235675, replib_290711, replib_335030
      2574 (Program type: Isothermal; Col... (show more) umn class: Standard non-polar; Column diameter: 0.20 mm; Column length: 25 m; Column type: Capillary; Start T: 250 C; CAS no: 738705; Active phase: SPB-1; Carrier gas: He; Data type: Kovats RI; Authors: Lora-Tamayo, C.; Rams, M.A.; Chacon, J.M.R., Gas Chromatographic Data for 187 Nitrogen- or Phosphorus-Containing Drugs and Metabolites of Toxicological Interest Analysed on Methyl Silicone Capillary Columns, J. Chromatogr., 374, 1986, 73-85.) NIST Spectra nist ri
    • Retention Index (Normal Alkane):

      2564.7 (Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column diameter: 0.32 mm; Column length: 12 m; Column type: Capillary; Heat rate: 10 K/min; Start T: 40 C; End T: 290 C; Start time: 1 min; CAS no: 738705; Active phase: SE-30; Carrier gas: He; Phase thickness: 0.25 um; Data type: Normal alkane RI; Authors: Neill, G.P.; Davies, N.W.; McLean, S., Automated screening procedure using gas chromatography-mass spectrometry for identification of drugs after their extraction from biological samples, J. Chromatogr., 565, 1991, 207-224.) NIST Spectra nist ri
      2605.9 (Program type: Complex; Column... (show more) class: Semi-standard non-polar; Column diameter: 0.32 mm; Column length: 15 m; Column type: Capillary; Description: 100 0C (0.4 min) ^ 25 0C/min -> 200 0C ^ 10 0C/min -> 290 0C (10 min); CAS no: 738705; Active phase: HG-5; Carrier gas: He; Phase thickness: 0.25 um; Data type: Normal alkane RI; Authors: Rasanen, I.; Kontinen, I.; Nokua, J.; Ojanpera, I.; Vuori, E., Precise gas chromatography with retention time locking in comprehensive toxicological screening for drugs in blood, J. Chromatogr. B, 788, 2003, 243-250.) NIST Spectra nist ri
      2582.4 (Program type: Complex; Column... (show more) class: Semi-standard non-polar; Column diameter: 0.32 mm; Column length: 15 m; Column type: Capillary; Description: 70 0C (0.7 min) ^ 20 0C/min -> 140 0C ^ 10 0C/min -> 290 0C (9.5 min); CAS no: 738705; Active phase: DB-5; Carrier gas: He; Phase thickness: 0.25 um; Data type: Normal alkane RI; Authors: Rasanen, I.; Ojanpera, I.; Vartiovaara, J.; Vuori, E.; Sunila, P., The advantage of dual-column approach and retention indices combined with refined reporting in gas chromatographic drug screening, J. Hi. Res. Chromatogr., 19, 1996, 313-321.) NIST Spectra nist ri
      2598.4 (Program type: Ramp; Column cl... (show more) ass: Semi-standard non-polar; Column diameter: 0.53 mm; Column length: 12 m; Column type: Capillary; Heat rate: .5 K/min; Start T: 100 C; End T: 310 C; End time: 10 min; Start time: 2 min; CAS no: 738705; Active phase: DB-5; Carrier gas: He; Phase thickness: 1.0 um; Data type: Normal alkane RI; Authors: Drummer, O.H.; Horomidis, S.; Kourtis, S.K.; Syrjanen, M.L.; Tippet, P., Capillary gas chromatographic drug screen for use in forensic toxicology, J. Anal. Toxicol., 18, 1994, 134-138.) NIST Spectra nist ri
    • Retention Index (Linear):

      2564 (Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column diameter: 0.75 mm; Column length: 30 m; Column type: Capillary; Heat rate: 10 K/min; Start T: 160 C; End T: 280 C; End time: 12 min; CAS no: 738705; Active phase: SPB-1; Carrier gas: He; Phase thickness: 1.0 um; Data type: Linear RI; Authors: Christ, D.W.; Noomano, P.; Rosas, M.; Rhone, D., Retention indices by wide-bore capillary gas chromatography with nitrogen-phosphorus detection, J. Anal. Toxicol., 12, 1988, 84-88.) NIST Spectra nist ri

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

Density: 1.3±0.1 g/cm3
Boiling Point: 526.0±60.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.4 mmHg at 25°C
Enthalpy of Vaporization: 80.0±3.0 kJ/mol
Flash Point: 271.9±32.9 °C
Index of Refraction: 1.609
Molar Refractivity: 80.3±0.3 cm3
#H bond acceptors: 7
#H bond donors: 4
#Freely Rotating Bonds: 5
#Rule of 5 Violations: 0
ACD/LogP: 0.79
ACD/LogD (pH 5.5): -0.28
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 3.89
ACD/LogD (pH 7.4): 1.00
ACD/BCF (pH 7.4): 3.14
ACD/KOC (pH 7.4): 72.87
Polar Surface Area: 106 Å2
Polarizability: 31.8±0.5 10-24cm3
Surface Tension: 53.9±3.0 dyne/cm
Molar Volume: 231.9±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) =  0.73
    Log Kow (Exper. database match) =  0.91
       Exper. Ref:  Hansch,C et al. (1995)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  449.23  (Adapted Stein & Brown method)
    Melting Pt (deg C):  188.88  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  7.52E-009  (Modified Grain method)
    MP  (exp database):  199-203 deg C
    Subcooled liquid VP: 5.13E-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):  2334
       log Kow used: 0.91 (expkow database)
       no-melting pt equation used
     Water Sol (Exper. database match) =  400 mg/L (25 deg C)
        Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  171.1 mg/L
    Wat Sol (Exper. database match) =  400.00
       Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Anilines (amino-meta)

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.39E-014  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.231E-012 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  0.91  (exp database)
  Log Kaw used:  -12.010  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  12.920
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.5922
   Biowin2 (Non-Linear Model)     :   0.9164
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.0385  (months      )
   Biowin4 (Primary Survey Model) :   3.3749  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.0889
   Biowin6 (MITI Non-Linear Model):   0.0172
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.1677
 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):  6.84E-005 Pa (5.13E-007 mm Hg)
  Log Koa (Koawin est  ): 12.920
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.0439 
       Octanol/air (Koa) model:  2.04 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.613 
       Mackay model           :  0.778 
       Octanol/air (Koa) model:  0.994 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 203.4228 E-12 cm3/molecule-sec
      Half-Life =     0.053 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.631 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.696 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  905
      Log Koc:  2.957 

 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: 0.91 (expkow database)

 Volatilization from Water:
    Henry LC:  2.39E-014 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 4.174E+010  hours   (1.739E+009 days)
    Half-Life from Model Lake : 4.553E+011  hours   (1.897E+010 days)

 Removal In Wastewater Treatment:
    Total removal:               1.88  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.79  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       9.95e-007       1.26         1000       
   Water     44.3            1.44e+003    1000       
   Soil      55.6            2.88e+003    1000       
   Sediment  0.0931          1.3e+004     0          
     Persistence Time: 1.27e+003 hr




                    

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