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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (5)transporters (1) Show 6 proteins XML

enzymes (5)transporters (1) Show 6 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:40 UTC

HMDB ID

HMDB0014583

Secondary Accession Numbers

HMDB14583

Metabolite Identification

Common Name

Trimethoprim

Description

Trimethoprim, also known as proloprim or trimpex, belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof. Trimethoprim is a very strong basic compound (based on its pKa). An aminopyrimidine antibiotic whose structure consists of pyrimidine 2,4-diamine and 1,2,3-trimethoxybenzene moieties linked by a methylene bridge.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0014583
     RDKit          3D
Trimethoprim
 39 40  0  0  0  0  0  0  0  0999 V2000
    2.1139    1.7348   -3.1707 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7427    0.9562   -2.1742 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0768    0.7374   -0.9746 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8165    1.2637   -0.7365 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1393    1.0632    0.4353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2084    1.6209    0.6777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3140    0.6935    0.4497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9582    0.0915    1.5342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9751   -0.7702    1.3678 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4149   -1.0884    0.1386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5058   -2.0134   -0.0385 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8078   -0.5195   -0.9128 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7717    0.3612   -0.8000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1849    0.9253   -1.9731 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7379    0.3049    1.4210 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0059   -0.2413    1.2177 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6233   -1.0061    2.1971 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9750   -1.2545    3.4416 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6530   -0.0189    0.0308 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9269   -0.5834   -0.1398 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0826   -1.8836   -0.6945 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6379    1.6750   -4.1393 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0392    2.7931   -2.8041 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0654    1.4098   -3.3683 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3682    1.8532   -1.5035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3033    2.5644    0.0751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2008    1.9915    1.7433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5792    0.3692    2.5146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1237   -1.9921   -0.8594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6352   -2.7153    0.7232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4972    1.8378   -2.3854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4117    0.3858   -2.4225 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2392    0.1157    2.3743 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7247   -0.2713    3.8949 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0627   -1.8824    3.2943 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6234   -1.7854    4.1444 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2584   -2.6515    0.0823 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1148   -2.1517   -1.1868 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8643   -1.9189   -1.4741 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
  5 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 16 19  2  0
 19 20  1  0
 20 21  1  0
 19  3  1  0
 13  7  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  6 26  1  0
  6 27  1  0
  8 28  1  0
 11 29  1  0
 11 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 18 34  1  0
 18 35  1  0
 18 36  1  0
 21 37  1  0
 21 38  1  0
 21 39  1  0
M  END

440
  Mrv0541 02231214412D          

 21 22  0  0  0  0            999 V2000
    6.3799    1.6995    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    1.6995    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509    2.5246    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -2.4256    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -1.1880    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509   -2.4256    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930   -2.4256    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509   -0.7755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509    0.0495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -1.1880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365    0.4620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6655    0.4620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6655    1.2870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365    1.2870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509    1.6995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -2.0130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -0.7755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -2.0130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0944    1.2870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075    1.2870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6655    2.9371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 13  1  0  0  0  0
  1 19  1  0  0  0  0
  2 14  1  0  0  0  0
  2 20  1  0  0  0  0
  3 15  1  0  0  0  0
  3 21  1  0  0  0  0
  4 16  2  0  0  0  0
  4 18  1  0  0  0  0
  5 17  1  0  0  0  0
  5 18  2  0  0  0  0
  6 16  1  0  0  0  0
  7 18  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 11  2  0  0  0  0
  9 12  1  0  0  0  0
 10 16  1  0  0  0  0
 10 17  2  0  0  0  0
 11 14  1  0  0  0  0
 12 13  2  0  0  0  0
 13 15  1  0  0  0  0
 14 15  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014583

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(CC2=CN=C(N)N=C2N)=CC(OC)=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C14H18N4O3/c1-19-10-5-8(6-11(20-2)12(10)21-3)4-9-7-17-14(16)18-13(9)15/h5-7H,4H2,1-3H3,(H4,15,16,17,18)

> <INCHI_KEY>
IEDVJHCEMCRBQM-UHFFFAOYSA-N

> <FORMULA>
C14H18N4O3

> <MOLECULAR_WEIGHT>
290.3177

> <EXACT_MASS>
290.137890462

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
29.713702230056416

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidine-2,4-diamine

> <ALOGPS_LOGP>
1.26

> <JCHEM_LOGP>
1.2839073299999995

> <ALOGPS_LOGS>
-2.67

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.33440529178666

> <JCHEM_PKA_STRONGEST_BASIC>
7.156319189418069

> <JCHEM_POLAR_SURFACE_AREA>
105.50999999999999

> <JCHEM_REFRACTIVITY>
81.5094

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.15e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
trimethoprim

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014583
     RDKit          3D
Trimethoprim
 39 40  0  0  0  0  0  0  0  0999 V2000
    2.1139    1.7348   -3.1707 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7427    0.9562   -2.1742 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0768    0.7374   -0.9746 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8165    1.2637   -0.7365 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1393    1.0632    0.4353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2084    1.6209    0.6777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3140    0.6935    0.4497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9582    0.0915    1.5342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9751   -0.7702    1.3678 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4149   -1.0884    0.1386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5058   -2.0134   -0.0385 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8078   -0.5195   -0.9128 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7717    0.3612   -0.8000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1849    0.9253   -1.9731 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7379    0.3049    1.4210 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0059   -0.2413    1.2177 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6233   -1.0061    2.1971 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9750   -1.2545    3.4416 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6530   -0.0189    0.0308 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9269   -0.5834   -0.1398 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0826   -1.8836   -0.6945 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6379    1.6750   -4.1393 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0392    2.7931   -2.8041 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0654    1.4098   -3.3683 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3682    1.8532   -1.5035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3033    2.5644    0.0751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2008    1.9915    1.7433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5792    0.3692    2.5146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1237   -1.9921   -0.8594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6352   -2.7153    0.7232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4972    1.8378   -2.3854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4117    0.3858   -2.4225 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2392    0.1157    2.3743 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7247   -0.2713    3.8949 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0627   -1.8824    3.2943 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6234   -1.7854    4.1444 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2584   -2.6515    0.0823 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1148   -2.1517   -1.1868 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8643   -1.9189   -1.4741 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
  5 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 16 19  2  0
 19 20  1  0
 20 21  1  0
 19  3  1  0
 13  7  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  6 26  1  0
  6 27  1  0
  8 28  1  0
 11 29  1  0
 11 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 18 34  1  0
 18 35  1  0
 18 36  1  0
 21 37  1  0
 21 38  1  0
 21 39  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 440                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      11.909   3.172   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       6.574   3.172   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       9.242   4.713   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       6.574  -4.528   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       5.241  -2.218   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       9.242  -4.528   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       3.907  -4.528   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       9.242  -1.448   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.242   0.092   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.908  -2.218   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.908   0.862   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.576   0.862   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.576   2.402   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.908   2.402   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.242   3.172   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.908  -3.758   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.574  -1.448   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.241  -3.758   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.243   2.402   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.241   2.402   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.576   5.483   0.000  0.00  0.00           C+0
CONECT    1   13   19                                                       
CONECT    2   14   20                                                       
CONECT    3   15   21                                                       
CONECT    4   16   18                                                       
CONECT    5   17   18                                                       
CONECT    6   16                                                            
CONECT    7   18                                                            
CONECT    8    9   10                                                       
CONECT    9    8   11   12                                                  
CONECT   10    8   16   17                                                  
CONECT   11    9   14                                                       
CONECT   12    9   13                                                       
CONECT   13    1   12   15                                                  
CONECT   14    2   11   15                                                  
CONECT   15    3   13   14                                                  
CONECT   16    4    6   10                                                  
CONECT   17    5   10                                                       
CONECT   18    4    5    7                                                  
CONECT   19    1                                                            
CONECT   20    2                                                            
CONECT   21    3                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

COMPND    HMDB0014583
HETATM    1  C1  UNL     1       2.114   1.735  -3.171  1.00  0.00           C  
HETATM    2  O1  UNL     1       2.743   0.956  -2.174  1.00  0.00           O  
HETATM    3  C2  UNL     1       2.077   0.737  -0.975  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.817   1.264  -0.736  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.139   1.063   0.435  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.208   1.621   0.678  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.314   0.693   0.450  1.00  0.00           C  
HETATM    8  C7  UNL     1      -2.958   0.091   1.534  1.00  0.00           C  
HETATM    9  N1  UNL     1      -3.975  -0.770   1.368  1.00  0.00           N  
HETATM   10  C8  UNL     1      -4.415  -1.088   0.139  1.00  0.00           C  
HETATM   11  N2  UNL     1      -5.506  -2.013  -0.039  1.00  0.00           N  
HETATM   12  N3  UNL     1      -3.808  -0.520  -0.913  1.00  0.00           N  
HETATM   13  C9  UNL     1      -2.772   0.361  -0.800  1.00  0.00           C  
HETATM   14  N4  UNL     1      -2.185   0.925  -1.973  1.00  0.00           N  
HETATM   15  C10 UNL     1       0.738   0.305   1.421  1.00  0.00           C  
HETATM   16  C11 UNL     1       2.006  -0.241   1.218  1.00  0.00           C  
HETATM   17  O2  UNL     1       2.623  -1.006   2.197  1.00  0.00           O  
HETATM   18  C12 UNL     1       1.975  -1.255   3.442  1.00  0.00           C  
HETATM   19  C13 UNL     1       2.653  -0.019   0.031  1.00  0.00           C  
HETATM   20  O3  UNL     1       3.927  -0.583  -0.140  1.00  0.00           O  
HETATM   21  C14 UNL     1       4.083  -1.884  -0.694  1.00  0.00           C  
HETATM   22  H1  UNL     1       2.638   1.675  -4.139  1.00  0.00           H  
HETATM   23  H2  UNL     1       2.039   2.793  -2.804  1.00  0.00           H  
HETATM   24  H3  UNL     1       1.065   1.410  -3.368  1.00  0.00           H  
HETATM   25  H4  UNL     1       0.368   1.853  -1.504  1.00  0.00           H  
HETATM   26  H5  UNL     1      -1.303   2.564   0.075  1.00  0.00           H  
HETATM   27  H6  UNL     1      -1.201   1.991   1.743  1.00  0.00           H  
HETATM   28  H7  UNL     1      -2.579   0.369   2.515  1.00  0.00           H  
HETATM   29  H8  UNL     1      -6.124  -1.992  -0.859  1.00  0.00           H  
HETATM   30  H9  UNL     1      -5.635  -2.715   0.723  1.00  0.00           H  
HETATM   31  H10 UNL     1      -2.497   1.838  -2.385  1.00  0.00           H  
HETATM   32  H11 UNL     1      -1.412   0.386  -2.423  1.00  0.00           H  
HETATM   33  H12 UNL     1       0.239   0.116   2.374  1.00  0.00           H  
HETATM   34  H13 UNL     1       1.725  -0.271   3.895  1.00  0.00           H  
HETATM   35  H14 UNL     1       1.063  -1.882   3.294  1.00  0.00           H  
HETATM   36  H15 UNL     1       2.623  -1.785   4.144  1.00  0.00           H  
HETATM   37  H16 UNL     1       4.258  -2.651   0.082  1.00  0.00           H  
HETATM   38  H17 UNL     1       3.115  -2.152  -1.187  1.00  0.00           H  
HETATM   39  H18 UNL     1       4.864  -1.919  -1.474  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3
CONECT    3    4    4   19
CONECT    4    5   25
CONECT    5    6   15   15
CONECT    6    7   26   27
CONECT    7    8    8   13
CONECT    8    9   28
CONECT    9   10   10
CONECT   10   11   12
CONECT   11   29   30
CONECT   12   13   13
CONECT   13   14
CONECT   14   31   32
CONECT   15   16   33
CONECT   16   17   19   19
CONECT   17   18
CONECT   18   34   35   36
CONECT   19   20
CONECT   20   21
CONECT   21   37   38   39
END

HMDB0014583
     RDKit          3D
Trimethoprim
 39 40  0  0  0  0  0  0  0  0999 V2000
    2.1139    1.7348   -3.1707 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7427    0.9562   -2.1742 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0768    0.7374   -0.9746 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8165    1.2637   -0.7365 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1393    1.0632    0.4353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2084    1.6209    0.6777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3140    0.6935    0.4497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9582    0.0915    1.5342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9751   -0.7702    1.3678 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4149   -1.0884    0.1386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5058   -2.0134   -0.0385 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8078   -0.5195   -0.9128 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7717    0.3612   -0.8000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1849    0.9253   -1.9731 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7379    0.3049    1.4210 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0059   -0.2413    1.2177 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6233   -1.0061    2.1971 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9750   -1.2545    3.4416 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6530   -0.0189    0.0308 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9269   -0.5834   -0.1398 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0826   -1.8836   -0.6945 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6379    1.6750   -4.1393 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0392    2.7931   -2.8041 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0654    1.4098   -3.3683 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3682    1.8532   -1.5035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3033    2.5644    0.0751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2008    1.9915    1.7433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5792    0.3692    2.5146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1237   -1.9921   -0.8594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6352   -2.7153    0.7232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4972    1.8378   -2.3854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4117    0.3858   -2.4225 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2392    0.1157    2.3743 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7247   -0.2713    3.8949 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0627   -1.8824    3.2943 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6234   -1.7854    4.1444 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2584   -2.6515    0.0823 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1148   -2.1517   -1.1868 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8643   -1.9189   -1.4741 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
  5 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 16 19  2  0
 19 20  1  0
 20 21  1  0
 19  3  1  0
 13  7  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  6 26  1  0
  6 27  1  0
  8 28  1  0
 11 29  1  0
 11 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 18 34  1  0
 18 35  1  0
 18 36  1  0
 21 37  1  0
 21 38  1  0
 21 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2,4-Diamino-5-(3,4,5-trimethoxybenzyl)pyrimidine	ChEBI
5-[(3,4,5-Trimethoxyphenyl)methyl]-2,4-pyrimidinediamine	ChEBI
Proloprim	ChEBI
Trimpex	ChEBI
CO-Trimoxazole	HMDB

Chemical Formula

C₁₄H₁₈N₄O₃

Average Molecular Weight

290.3177

Monoisotopic Molecular Weight

290.137890462

IUPAC Name

5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidine-2,4-diamine

Traditional Name

trimethoprim

CAS Registry Number

738-70-5

SMILES

COC1=CC(CC2=CN=C(N)N=C2N)=CC(OC)=C1OC

InChI Identifier

InChI=1S/C14H18N4O3/c1-19-10-5-8(6-11(20-2)12(10)21-3)4-9-7-17-14(16)18-13(9)15/h5-7H,4H2,1-3H3,(H4,15,16,17,18)

InChI Key

IEDVJHCEMCRBQM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Phenoxy compound
Anisole
Methoxybenzene
Alkyl aryl ether
Aminopyrimidine
Monocyclic benzene moiety
Pyrimidine
Imidolactam
Heteroaromatic compound
Organoheterocyclic compound
Ether
Azacycle
Organic oxygen compound
Amine
Primary amine
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

aminopyrimidine (CHEBI:45924 )
methoxybenzene (CHEBI:45924 )
a small molecule (CPD0-1581 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0014583)

Source

Exogenous

Exogenous (HMDB: HMDB0014583)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	199 - 203 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.62 g/L	Not Available
LogP	0.6	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	170.8	30932474
[M+H]+	Not Available	171.225	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000787

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.62 g/L	ALOGPS
logP	1.26	ALOGPS
logP	1.28	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	17.33	ChemAxon
pKa (Strongest Basic)	7.16	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	105.51 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	81.51 m³·mol⁻¹	ChemAxon
Polarizability	29.71 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	170.296	31661259
DarkChem	[M-H]-	169.608	31661259
DeepCCS	[M+H]+	166.935	30932474
DeepCCS	[M-H]-	164.577	30932474
DeepCCS	[M-2H]-	197.463	30932474
DeepCCS	[M+Na]+	173.028	30932474
AllCCS	[M+H]+	166.7	32859911
AllCCS	[M+H-H2O]+	163.1	32859911
AllCCS	[M+NH4]+	170.0	32859911
AllCCS	[M+Na]+	170.9	32859911
AllCCS	[M-H]-	171.2	32859911
AllCCS	[M+Na-2H]-	171.1	32859911
AllCCS	[M+HCOO]-	171.1	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	2.12 minutes	32390414
Predicted by Siyang on May 30, 2022	9.9937 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.98 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	36.0 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	646.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	209.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	124.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	164.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	62.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	282.6 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	350.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	392.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	717.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	196.2 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	798.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	210.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	246.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	412.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	243.6 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	20.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Trimethoprim	COC1=CC(CC2=CN=C(N)N=C2N)=CC(OC)=C1OC	3800.3	Standard polar	33892256
Trimethoprim	COC1=CC(CC2=CN=C(N)N=C2N)=CC(OC)=C1OC	2577.3	Standard non polar	33892256
Trimethoprim	COC1=CC(CC2=CN=C(N)N=C2N)=CC(OC)=C1OC	2638.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Trimethoprim,1TMS,isomer #1	COC1=CC(CC2=CN=C(N[Si](C)(C)C)N=C2N)=CC(OC)=C1OC	2666.2	Semi standard non polar	33892256
Trimethoprim,1TMS,isomer #1	COC1=CC(CC2=CN=C(N[Si](C)(C)C)N=C2N)=CC(OC)=C1OC	2610.4	Standard non polar	33892256
Trimethoprim,1TMS,isomer #1	COC1=CC(CC2=CN=C(N[Si](C)(C)C)N=C2N)=CC(OC)=C1OC	4269.8	Standard polar	33892256
Trimethoprim,1TMS,isomer #2	COC1=CC(CC2=CN=C(N)N=C2N[Si](C)(C)C)=CC(OC)=C1OC	2679.4	Semi standard non polar	33892256
Trimethoprim,1TMS,isomer #2	COC1=CC(CC2=CN=C(N)N=C2N[Si](C)(C)C)=CC(OC)=C1OC	2606.6	Standard non polar	33892256
Trimethoprim,1TMS,isomer #2	COC1=CC(CC2=CN=C(N)N=C2N[Si](C)(C)C)=CC(OC)=C1OC	4121.0	Standard polar	33892256
Trimethoprim,2TMS,isomer #1	COC1=CC(CC2=CN=C(N[Si](C)(C)C)N=C2N[Si](C)(C)C)=CC(OC)=C1OC	2632.7	Semi standard non polar	33892256
Trimethoprim,2TMS,isomer #1	COC1=CC(CC2=CN=C(N[Si](C)(C)C)N=C2N[Si](C)(C)C)=CC(OC)=C1OC	2623.0	Standard non polar	33892256
Trimethoprim,2TMS,isomer #1	COC1=CC(CC2=CN=C(N[Si](C)(C)C)N=C2N[Si](C)(C)C)=CC(OC)=C1OC	4011.1	Standard polar	33892256
Trimethoprim,2TMS,isomer #2	COC1=CC(CC2=CN=C(N([Si](C)(C)C)[Si](C)(C)C)N=C2N)=CC(OC)=C1OC	2599.1	Semi standard non polar	33892256
Trimethoprim,2TMS,isomer #2	COC1=CC(CC2=CN=C(N([Si](C)(C)C)[Si](C)(C)C)N=C2N)=CC(OC)=C1OC	2659.9	Standard non polar	33892256
Trimethoprim,2TMS,isomer #2	COC1=CC(CC2=CN=C(N([Si](C)(C)C)[Si](C)(C)C)N=C2N)=CC(OC)=C1OC	3946.1	Standard polar	33892256
Trimethoprim,2TMS,isomer #3	COC1=CC(CC2=CN=C(N)N=C2N([Si](C)(C)C)[Si](C)(C)C)=CC(OC)=C1OC	2553.6	Semi standard non polar	33892256
Trimethoprim,2TMS,isomer #3	COC1=CC(CC2=CN=C(N)N=C2N([Si](C)(C)C)[Si](C)(C)C)=CC(OC)=C1OC	2709.4	Standard non polar	33892256
Trimethoprim,2TMS,isomer #3	COC1=CC(CC2=CN=C(N)N=C2N([Si](C)(C)C)[Si](C)(C)C)=CC(OC)=C1OC	3870.4	Standard polar	33892256
Trimethoprim,3TMS,isomer #1	COC1=CC(CC2=CN=C(N([Si](C)(C)C)[Si](C)(C)C)N=C2N[Si](C)(C)C)=CC(OC)=C1OC	2610.6	Semi standard non polar	33892256
Trimethoprim,3TMS,isomer #1	COC1=CC(CC2=CN=C(N([Si](C)(C)C)[Si](C)(C)C)N=C2N[Si](C)(C)C)=CC(OC)=C1OC	2621.2	Standard non polar	33892256
Trimethoprim,3TMS,isomer #1	COC1=CC(CC2=CN=C(N([Si](C)(C)C)[Si](C)(C)C)N=C2N[Si](C)(C)C)=CC(OC)=C1OC	3579.4	Standard polar	33892256
Trimethoprim,3TMS,isomer #2	COC1=CC(CC2=CN=C(N[Si](C)(C)C)N=C2N([Si](C)(C)C)[Si](C)(C)C)=CC(OC)=C1OC	2604.1	Semi standard non polar	33892256
Trimethoprim,3TMS,isomer #2	COC1=CC(CC2=CN=C(N[Si](C)(C)C)N=C2N([Si](C)(C)C)[Si](C)(C)C)=CC(OC)=C1OC	2674.5	Standard non polar	33892256
Trimethoprim,3TMS,isomer #2	COC1=CC(CC2=CN=C(N[Si](C)(C)C)N=C2N([Si](C)(C)C)[Si](C)(C)C)=CC(OC)=C1OC	3678.5	Standard polar	33892256
Trimethoprim,4TMS,isomer #1	COC1=CC(CC2=CN=C(N([Si](C)(C)C)[Si](C)(C)C)N=C2N([Si](C)(C)C)[Si](C)(C)C)=CC(OC)=C1OC	2649.8	Semi standard non polar	33892256
Trimethoprim,4TMS,isomer #1	COC1=CC(CC2=CN=C(N([Si](C)(C)C)[Si](C)(C)C)N=C2N([Si](C)(C)C)[Si](C)(C)C)=CC(OC)=C1OC	2655.1	Standard non polar	33892256
Trimethoprim,4TMS,isomer #1	COC1=CC(CC2=CN=C(N([Si](C)(C)C)[Si](C)(C)C)N=C2N([Si](C)(C)C)[Si](C)(C)C)=CC(OC)=C1OC	3287.5	Standard polar	33892256
Trimethoprim,1TBDMS,isomer #1	COC1=CC(CC2=CN=C(N[Si](C)(C)C(C)(C)C)N=C2N)=CC(OC)=C1OC	2853.9	Semi standard non polar	33892256
Trimethoprim,1TBDMS,isomer #1	COC1=CC(CC2=CN=C(N[Si](C)(C)C(C)(C)C)N=C2N)=CC(OC)=C1OC	2825.4	Standard non polar	33892256
Trimethoprim,1TBDMS,isomer #1	COC1=CC(CC2=CN=C(N[Si](C)(C)C(C)(C)C)N=C2N)=CC(OC)=C1OC	4235.7	Standard polar	33892256
Trimethoprim,1TBDMS,isomer #2	COC1=CC(CC2=CN=C(N)N=C2N[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC	2873.4	Semi standard non polar	33892256
Trimethoprim,1TBDMS,isomer #2	COC1=CC(CC2=CN=C(N)N=C2N[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC	2817.2	Standard non polar	33892256
Trimethoprim,1TBDMS,isomer #2	COC1=CC(CC2=CN=C(N)N=C2N[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC	4105.2	Standard polar	33892256
Trimethoprim,2TBDMS,isomer #1	COC1=CC(CC2=CN=C(N[Si](C)(C)C(C)(C)C)N=C2N[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC	3031.7	Semi standard non polar	33892256
Trimethoprim,2TBDMS,isomer #1	COC1=CC(CC2=CN=C(N[Si](C)(C)C(C)(C)C)N=C2N[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC	3020.8	Standard non polar	33892256
Trimethoprim,2TBDMS,isomer #1	COC1=CC(CC2=CN=C(N[Si](C)(C)C(C)(C)C)N=C2N[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC	3981.5	Standard polar	33892256
Trimethoprim,2TBDMS,isomer #2	COC1=CC(CC2=CN=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C2N)=CC(OC)=C1OC	3033.6	Semi standard non polar	33892256
Trimethoprim,2TBDMS,isomer #2	COC1=CC(CC2=CN=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C2N)=CC(OC)=C1OC	3086.2	Standard non polar	33892256
Trimethoprim,2TBDMS,isomer #2	COC1=CC(CC2=CN=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C2N)=CC(OC)=C1OC	3916.1	Standard polar	33892256
Trimethoprim,2TBDMS,isomer #3	COC1=CC(CC2=CN=C(N)N=C2N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC	2988.0	Semi standard non polar	33892256
Trimethoprim,2TBDMS,isomer #3	COC1=CC(CC2=CN=C(N)N=C2N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC	3084.9	Standard non polar	33892256
Trimethoprim,2TBDMS,isomer #3	COC1=CC(CC2=CN=C(N)N=C2N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC	3876.2	Standard polar	33892256
Trimethoprim,3TBDMS,isomer #1	COC1=CC(CC2=CN=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C2N[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC	3159.7	Semi standard non polar	33892256
Trimethoprim,3TBDMS,isomer #1	COC1=CC(CC2=CN=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C2N[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC	3230.2	Standard non polar	33892256
Trimethoprim,3TBDMS,isomer #1	COC1=CC(CC2=CN=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C2N[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC	3689.2	Standard polar	33892256
Trimethoprim,3TBDMS,isomer #2	COC1=CC(CC2=CN=C(N[Si](C)(C)C(C)(C)C)N=C2N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC	3177.4	Semi standard non polar	33892256
Trimethoprim,3TBDMS,isomer #2	COC1=CC(CC2=CN=C(N[Si](C)(C)C(C)(C)C)N=C2N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC	3220.9	Standard non polar	33892256
Trimethoprim,3TBDMS,isomer #2	COC1=CC(CC2=CN=C(N[Si](C)(C)C(C)(C)C)N=C2N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC	3774.4	Standard polar	33892256
Trimethoprim,4TBDMS,isomer #1	COC1=CC(CC2=CN=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C2N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC	3362.7	Semi standard non polar	33892256
Trimethoprim,4TBDMS,isomer #1	COC1=CC(CC2=CN=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C2N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC	3434.3	Standard non polar	33892256
Trimethoprim,4TBDMS,isomer #1	COC1=CC(CC2=CN=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C2N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC	3533.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Trimethoprim EI-B (Non-derivatized)	splash10-0006-5390000000-e68103f64cbb997e5776	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Trimethoprim EI-B (Non-derivatized)	splash10-0006-5390000000-e68103f64cbb997e5776	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Trimethoprim GC-MS (Non-derivatized) - 70eV, Positive	splash10-072c-0390000000-14ead3ead386e06ae454	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Trimethoprim GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Trimethoprim LC-ESI-qTof , Positive-QTOF	splash10-03na-2690000000-39babdc7b45a0aa0adf7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Trimethoprim LC-ESI-ITFT , positive-QTOF	splash10-0089-0290000000-32000410829186ca112c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Trimethoprim LC-ESI-ITFT , positive-QTOF	splash10-0006-0090000000-44ccaa9725303a7db8a4	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Trimethoprim LC-ESI-ITFT , positive-QTOF	splash10-0006-0090000000-af77a44791c8867aad66	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Trimethoprim LC-ESI-ITFT , positive-QTOF	splash10-0006-0190000000-8eb1449e3f800368c863	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Trimethoprim LC-ESI-ITFT , positive-QTOF	splash10-03n9-0190000000-deb1664d211c2227b048	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Trimethoprim LC-ESI-ITFT , positive-QTOF	splash10-077i-0590000000-ae48b54f4879c1551670	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Trimethoprim LC-ESI-ITFT , positive-QTOF	splash10-0089-1950000000-5084ea4b328a585b675d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Trimethoprim LC-ESI-ITFT , positive-QTOF	splash10-0006-0090000000-fb9fa4e4130917b6e6ff	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Trimethoprim LC-ESI-ITFT , positive-QTOF	splash10-0006-0090000000-15d83f92b30f466cd587	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Trimethoprim LC-ESI-ITFT , positive-QTOF	splash10-0006-0190000000-f95e0c038a6aa70dc02e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Trimethoprim LC-ESI-ITFT , positive-QTOF	splash10-03na-0190000000-72c88d8f9739c7d29714	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Trimethoprim LC-ESI-ITFT , positive-QTOF	splash10-077i-0590000000-9c0f5662b9713adab9cb	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Trimethoprim LC-ESI-ITFT , positive-QTOF	splash10-0089-1950000000-8b16041ba3b127d299ba	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Trimethoprim LC-ESI-ITFT , positive-QTOF	splash10-0089-0290000000-6a16da6c03a03fd87f34	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Trimethoprim LC-ESI-QQ , positive-QTOF	splash10-0006-0090000000-145bf44afce31ab82f64	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Trimethoprim LC-ESI-QQ , positive-QTOF	splash10-0006-0090000000-68ca013641f0c338b3a2	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Trimethoprim LC-ESI-QQ , positive-QTOF	splash10-008c-0290000000-d56028ecf88d373b83bd	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Trimethoprim LC-ESI-QQ , positive-QTOF	splash10-03n9-0590000000-15246e14a33089adf87d	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trimethoprim 10V, Positive-QTOF	splash10-0006-0090000000-ab604617a206ca211558	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trimethoprim 20V, Positive-QTOF	splash10-006x-0190000000-20fc4fb0fdca747b84f8	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trimethoprim 40V, Positive-QTOF	splash10-00dj-3690000000-0ec38b6068b0db0dfb83	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trimethoprim 10V, Negative-QTOF	splash10-000i-0090000000-8e413946db77cf7ccfea	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trimethoprim 20V, Negative-QTOF	splash10-000i-1090000000-691ddb4fa4a66277fa2e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trimethoprim 40V, Negative-QTOF	splash10-0006-7390000000-a01859f18f535ce1b096	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00440	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00440	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00440

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5376

KEGG Compound ID

C01965

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Trimethoprim

METLIN ID

Not Available

PubChem Compound

5578

PDB ID

Not Available

ChEBI ID

45924

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Brumfitt W, Hamilton-Miller JM: Limitations of and indications for the use of co-trimoxazole. J Chemother. 1994 Feb;6(1):3-11. [PubMed:8071675 ]
Brumfitt W, Hamilton-Miller JM: Reassessment of the rationale for the combinations of sulphonamides with diaminopyrimidines. J Chemother. 1993 Dec;5(6):465-9. [PubMed:8195839 ]
Johnson JR, Manges AR, O'Bryan TT, Riley LW: A disseminated multidrug-resistant clonal group of uropathogenic Escherichia coli in pyelonephritis. Lancet. 2002 Jun 29;359(9325):2249-51. [PubMed:12103291 ]
Felmingham D, Reinert RR, Hirakata Y, Rodloff A: Increasing prevalence of antimicrobial resistance among isolates of Streptococcus pneumoniae from the PROTEKT surveillance study, and compatative in vitro activity of the ketolide, telithromycin. J Antimicrob Chemother. 2002 Sep;50 Suppl S1:25-37. [PubMed:12239226 ]
Bean DC, Livermore DM, Papa I, Hall LM: Resistance among Escherichia coli to sulphonamides and other antimicrobials now little used in man. J Antimicrob Chemother. 2005 Nov;56(5):962-4. Epub 2005 Sep 8. [PubMed:16150859 ]

Enzymes

Enzyme Details

1. Dihydrofolate reductase

General function:: Involved in dihydrofolate reductase activity
Specific function:: Key enzyme in folate metabolism. Contributes to the de novo mitochondrial thymidylate biosynthesis pathway. Catalyzes an essential reaction for de novo glycine and purine synthesis, and for DNA precursor synthesis. Binds its own mRNA and that of DHFRL1.
Gene Name:: DHFR
Uniprot ID:: P00374
Molecular weight:: 21452.61

References

Laskowska E, Kuczynska-Wisnik D, Bak M, Lipinska B: Trimethoprim induces heat shock proteins and protein aggregation in E. coli cells. Curr Microbiol. 2003 Oct;47(4):286-9. [PubMed:14629008 ]
Floris-Moore MA, Amodio-Groton MI, Catalano MT: Adverse reactions to trimethoprim/sulfamethoxazole in AIDS. Ann Pharmacother. 2003 Dec;37(12):1810-3. [PubMed:14632594 ]
Rosowsky A, Fu H, Chan DC, Queener SF: Synthesis of 2,4-diamino-6-[2'-O-(omega-carboxyalkyl)oxydibenz[b,f]azepin-5-yl]methylpteridine s as potent and selective inhibitors of Pneumocystis carinii, Toxoplasma gondii, and Mycobacterium avium dihydrofolate reductase. J Med Chem. 2004 May 6;47(10):2475-85. [PubMed:15115391 ]
Nahimana A, Rabodonirina M, Bille J, Francioli P, Hauser PM: Mutations of Pneumocystis jirovecii dihydrofolate reductase associated with failure of prophylaxis. Antimicrob Agents Chemother. 2004 Nov;48(11):4301-5. [PubMed:15504856 ]
Barrow EW, Bourne PC, Barrow WW: Functional cloning of Bacillus anthracis dihydrofolate reductase and confirmation of natural resistance to trimethoprim. Antimicrob Agents Chemother. 2004 Dec;48(12):4643-9. [PubMed:15561838 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

2. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

3. Cytochrome P450 2C9

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:: CYP2C9
Uniprot ID:: P11712
Molecular weight:: 55627.365

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

4. Cytochrome P450 2C8

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti-cancer drug paclitaxel (taxol).
Gene Name:: CYP2C8
Uniprot ID:: P10632
Molecular weight:: 55824.275

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

5. Thymidylate synthase

General function:: Involved in thymidylate synthase activity
Specific function:: Contributes to the de novo mitochondrial thymidylate biosynthesis pathway.
Gene Name:: TYMS
Uniprot ID:: P04818
Molecular weight:: 35715.65

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Gamarro F, Yu PL, Zhao J, Edman U, Greene PJ, Santi D: Trypanosoma brucei dihydrofolate reductase-thymidylate synthase: gene isolation and expression and characterization of the enzyme. Mol Biochem Parasitol. 1995 Jun;72(1-2):11-22. [PubMed:8538681 ]
Rosowsky A, Papoulis AT, Forsch RA, Queener SF: Synthesis and antiparasitic and antitumor activity of 2, 4-diamino-6-(arylmethyl)-5,6,7,8-tetrahydroquinazoline analogues of piritrexim. J Med Chem. 1999 Mar 25;42(6):1007-17. [PubMed:10090784 ]
Reche P, Arrebola R, Santi DV, Gonzalez-Pacanowska D, Ruiz-Perez LM: Expression and characterization of the Trypanosoma cruzi dihydrofolate reductase domain. Mol Biochem Parasitol. 1996 Feb-Mar;76(1-2):175-85. [PubMed:8920005 ]
Oefner C, Parisi S, Schulz H, Lociuro S, Dale GE: Inhibitory properties and X-ray crystallographic study of the binding of AR-101, AR-102 and iclaprim in ternary complexes with NADPH and dihydrofolate reductase from Staphylococcus aureus. Acta Crystallogr D Biol Crystallogr. 2009 Aug;65(Pt 8):751-7. doi: 10.1107/S0907444909013936. Epub 2009 Jul 10. [PubMed:19622858 ]
Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]

Transporters

Enzyme Details

1. Multidrug resistance protein 1

General function:: Involved in ATP binding
Specific function:: Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:: ABCB1
Uniprot ID:: P08183
Molecular weight:: 141477.3

References

Romiti N, Tramonti G, Chieli E: Influence of different chemicals on MDR-1 P-glycoprotein expression and activity in the HK-2 proximal tubular cell line. Toxicol Appl Pharmacol. 2002 Sep 1;183(2):83-91. [PubMed:12387747 ]
Polli JW, Wring SA, Humphreys JE, Huang L, Morgan JB, Webster LO, Serabjit-Singh CS: Rational use of in vitro P-glycoprotein assays in drug discovery. J Pharmacol Exp Ther. 2001 Nov;299(2):620-8. [PubMed:11602674 ]

Showing metabocard for Trimethoprim (HMDB0014583)

MOL for HMDB0014583 (Trimethoprim)

3D MOL for HMDB0014583 (Trimethoprim)

3D SDF for HMDB0014583 (Trimethoprim)

3D-SDF for HMDB0014583 (Trimethoprim)

PDB for HMDB0014583 (Trimethoprim)

3D PDB for HMDB0014583 (Trimethoprim)

SMILES for HMDB0014583 (Trimethoprim)

INCHI for HMDB0014583 (Trimethoprim)

Structure for HMDB0014583 (Trimethoprim)

3D Structure for HMDB0014583 (Trimethoprim)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References

References

Transporters

References