Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:55 UTC

HMDB ID

HMDB0015288

Secondary Accession Numbers

HMDB15288

Metabolite Identification

Common Name

Trimetrexate

Description

Trimetrexate, also known as trimetrexic acid or neutrexin, belongs to the class of organic compounds known as quinazolinamines. These are heterocyclic aromatic compounds containing a quianazoline moiety substituted by one or more amine groups. Trimetrexate is a drug which is used for use, with concurrent leucovorin administration (leucovorin protection), as an alternative therapy for the treatment of moderate-to-severe pneumocystis carinii pneumonia (pcp) in immunocompromised patients, including patients with the acquired immunodeficiency syndrome (aids). also used to treat several types of cancer including colon cancer. It has been investigated for use in treating leiomyosarcoma.It is a methotrexate (MTX) analog that is active against transport-deficient MTX-resistant tumor cells that overcome the acquired and natural resistance to methotrexate. Trimetrexate is a very strong basic compound (based on its pKa). Trimetrexate is a potentially toxic compound. It is a dihydrofolate reductase inhibitor. It has been used with leucovorin in treating pneumocystis pneumonia. Other uses include skin lymphoma. Trimetrexate is a quinazoline derivative.

Structure

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

1157
  Mrv0541 02231215172D          

 27 29  0  0  0  0            999 V2000
    8.5698   -1.9212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0083    0.5483    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0019   -1.1017    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1504    0.5593    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    1.8195    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075    0.5820    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -0.6556    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930    1.8195    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7214    0.5648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9740    0.1408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4343    0.1496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2364    0.5820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2364    1.4070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7214    1.4241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9740    1.8481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9644   -0.6841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8633    0.1440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    0.1695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5793    0.5537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8601   -0.6810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5730   -1.0963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2922    0.1385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2890   -0.6865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075    1.4070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8537   -2.3310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0115    1.3733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7180   -0.6920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 21  1  0  0  0  0
  1 25  1  0  0  0  0
  2 22  1  0  0  0  0
  2 26  1  0  0  0  0
  3 23  1  0  0  0  0
  3 27  1  0  0  0  0
  4 11  1  0  0  0  0
  4 17  1  0  0  0  0
  5 13  1  0  0  0  0
  5 24  2  0  0  0  0
  6 18  2  0  0  0  0
  6 24  1  0  0  0  0
  7 18  1  0  0  0  0
  8 24  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  9 14  1  0  0  0  0
 10 12  1  0  0  0  0
 10 16  1  0  0  0  0
 12 13  2  0  0  0  0
 12 18  1  0  0  0  0
 13 15  1  0  0  0  0
 14 15  2  0  0  0  0
 17 19  2  0  0  0  0
 17 20  1  0  0  0  0
 19 22  1  0  0  0  0
 20 21  2  0  0  0  0
 21 23  1  0  0  0  0
 22 23  2  0  0  0  0
M  END

HMDB0015288
     RDKit          3D
Trimetrexate
 50 52  0  0  0  0  0  0  0  0999 V2000
   -4.9490   -2.4766   -2.2337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3224   -1.3131   -1.5201 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3206   -0.5964   -0.8917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9778   -0.9894   -0.9463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9901   -0.2727   -0.3201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6181   -0.7354   -0.4166 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4354   -0.0062    0.2272 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7540   -0.5884    0.0369 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9680   -1.7136   -0.6862 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2585   -2.2338   -0.8380 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3328   -1.6224   -0.2627 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5801   -2.1314   -0.4113 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6333   -1.5359    0.1525 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9635   -2.0824   -0.0088 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4295   -0.4324    0.8628 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2018    0.1196    1.0433 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1011    1.3003    1.8234 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1035   -0.4607    0.4825 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8530    0.0784    0.6529 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6014    1.3045    1.4390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3300    0.8621    0.3796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6504    1.2906    0.4611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0100    2.4273    1.1591 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9821    3.1650    1.8054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6324    0.5630   -0.1715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9363    0.9788   -0.0958 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5362    1.8626   -1.0245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2128   -2.2249   -3.0275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4795   -3.1800   -1.4922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8233   -3.0115   -2.6532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7259   -1.8873   -1.5026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4116   -1.5911   -0.9508 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3543    1.0344   -0.2177 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2689    0.0364    1.3455 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2032   -2.2794   -1.1839 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4346   -3.1338   -1.4158 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3107   -2.3725   -0.9440 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5525   -2.1715    0.8456 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8163    1.2559    2.7996 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3475    2.2125    1.3925 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5039    1.5712    1.2664 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1124    2.2032    1.1084 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5872    1.1268    2.5494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5708    1.4435    0.8811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2325    3.5427    1.1064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4241    3.9713    2.4520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4868    2.4602    2.5350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5464    2.1382   -0.6900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6464    1.3412   -2.0009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8920    2.7534   -1.1906 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  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
  5 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 22 25  2  0
 25 26  1  0
 26 27  1  0
 25  3  1  0
 19  8  1  0
 18 11  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  4 31  1  0
  6 32  1  0
  7 33  1  0
  7 34  1  0
  9 35  1  0
 10 36  1  0
 14 37  1  0
 14 38  1  0
 17 39  1  0
 17 40  1  0
 20 41  1  0
 20 42  1  0
 20 43  1  0
 21 44  1  0
 24 45  1  0
 24 46  1  0
 24 47  1  0
 27 48  1  0
 27 49  1  0
 27 50  1  0
M  END

1157
  Mrv0541 02231215172D          

 27 29  0  0  0  0            999 V2000
    8.5698   -1.9212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0083    0.5483    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0019   -1.1017    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1504    0.5593    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    1.8195    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075    0.5820    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -0.6556    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930    1.8195    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7214    0.5648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9740    0.1408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4343    0.1496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2364    0.5820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2364    1.4070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7214    1.4241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9740    1.8481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9644   -0.6841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8633    0.1440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    0.1695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5793    0.5537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8601   -0.6810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5730   -1.0963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2922    0.1385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2890   -0.6865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075    1.4070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8537   -2.3310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0115    1.3733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7180   -0.6920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 21  1  0  0  0  0
  1 25  1  0  0  0  0
  2 22  1  0  0  0  0
  2 26  1  0  0  0  0
  3 23  1  0  0  0  0
  3 27  1  0  0  0  0
  4 11  1  0  0  0  0
  4 17  1  0  0  0  0
  5 13  1  0  0  0  0
  5 24  2  0  0  0  0
  6 18  2  0  0  0  0
  6 24  1  0  0  0  0
  7 18  1  0  0  0  0
  8 24  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  9 14  1  0  0  0  0
 10 12  1  0  0  0  0
 10 16  1  0  0  0  0
 12 13  2  0  0  0  0
 12 18  1  0  0  0  0
 13 15  1  0  0  0  0
 14 15  2  0  0  0  0
 17 19  2  0  0  0  0
 17 20  1  0  0  0  0
 19 22  1  0  0  0  0
 20 21  2  0  0  0  0
 21 23  1  0  0  0  0
 22 23  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015288

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(NCC2=C(C)C3=C(C=C2)N=C(N)N=C3N)=CC(OC)=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C19H23N5O3/c1-10-11(5-6-13-16(10)18(20)24-19(21)23-13)9-22-12-7-14(25-2)17(27-4)15(8-12)26-3/h5-8,22H,9H2,1-4H3,(H4,20,21,23,24)

> <INCHI_KEY>
NOYPYLRCIDNJJB-UHFFFAOYSA-N

> <FORMULA>
C19H23N5O3

> <MOLECULAR_WEIGHT>
369.4176

> <EXACT_MASS>
369.180089627

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
40.23957114843252

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-methyl-6-{[(3,4,5-trimethoxyphenyl)amino]methyl}quinazoline-2,4-diamine

> <ALOGPS_LOGP>
2.36

> <JCHEM_LOGP>
2.2781130193333325

> <ALOGPS_LOGS>
-4.08

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.038573321274995

> <JCHEM_PKA_STRONGEST_BASIC>
7.539544844201364

> <JCHEM_POLAR_SURFACE_AREA>
117.53999999999999

> <JCHEM_REFRACTIVITY>
107.69800000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.09e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
trimetrexate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015288
     RDKit          3D
Trimetrexate
 50 52  0  0  0  0  0  0  0  0999 V2000
   -4.9490   -2.4766   -2.2337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3224   -1.3131   -1.5201 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3206   -0.5964   -0.8917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9778   -0.9894   -0.9463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9901   -0.2727   -0.3201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6181   -0.7354   -0.4166 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4354   -0.0062    0.2272 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7540   -0.5884    0.0369 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9680   -1.7136   -0.6862 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2585   -2.2338   -0.8380 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3328   -1.6224   -0.2627 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5801   -2.1314   -0.4113 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6333   -1.5359    0.1525 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9635   -2.0824   -0.0088 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4295   -0.4324    0.8628 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2018    0.1196    1.0433 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1011    1.3003    1.8234 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1035   -0.4607    0.4825 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8530    0.0784    0.6529 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6014    1.3045    1.4390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3300    0.8621    0.3796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6504    1.2906    0.4611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0100    2.4273    1.1591 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9821    3.1650    1.8054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6324    0.5630   -0.1715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9363    0.9788   -0.0958 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5362    1.8626   -1.0245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2128   -2.2249   -3.0275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4795   -3.1800   -1.4922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8233   -3.0115   -2.6532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7259   -1.8873   -1.5026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4116   -1.5911   -0.9508 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3543    1.0344   -0.2177 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2689    0.0364    1.3455 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2032   -2.2794   -1.1839 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4346   -3.1338   -1.4158 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3107   -2.3725   -0.9440 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5525   -2.1715    0.8456 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8163    1.2559    2.7996 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3475    2.2125    1.3925 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5039    1.5712    1.2664 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1124    2.2032    1.1084 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5872    1.1268    2.5494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5708    1.4435    0.8811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2325    3.5427    1.1064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4241    3.9713    2.4520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4868    2.4602    2.5350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5464    2.1382   -0.6900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6464    1.3412   -2.0009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8920    2.7534   -1.1906 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  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
  5 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 22 25  2  0
 25 26  1  0
 26 27  1  0
 25  3  1  0
 19  8  1  0
 18 11  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  4 31  1  0
  6 32  1  0
  7 33  1  0
  7 34  1  0
  9 35  1  0
 10 36  1  0
 14 37  1  0
 14 38  1  0
 17 39  1  0
 17 40  1  0
 20 41  1  0
 20 42  1  0
 20 43  1  0
 21 44  1  0
 24 45  1  0
 24 46  1  0
 24 47  1  0
 27 48  1  0
 27 49  1  0
 27 50  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1157                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      15.997  -3.586   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      18.682   1.023   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      18.670  -2.057   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0      13.347   1.044   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       6.574   3.396   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       5.241   1.086   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       6.574  -1.224   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0       3.907   3.396   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      10.680   1.054   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.285   0.263   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.011   0.279   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.908   1.086   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.908   2.626   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.680   2.658   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.285   3.450   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.267  -1.277   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.678   0.269   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.574   0.316   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      16.015   1.034   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      14.672  -1.271   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      16.003  -2.046   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      17.345   0.259   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      17.339  -1.281   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.241   2.626   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      14.660  -4.351   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      18.688   2.563   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      20.007  -1.292   0.000  0.00  0.00           C+0
CONECT    1   21   25                                                       
CONECT    2   22   26                                                       
CONECT    3   23   27                                                       
CONECT    4   11   17                                                       
CONECT    5   13   24                                                       
CONECT    6   18   24                                                       
CONECT    7   18                                                            
CONECT    8   24                                                            
CONECT    9   10   11   14                                                  
CONECT   10    9   12   16                                                  
CONECT   11    4    9                                                       
CONECT   12   10   13   18                                                  
CONECT   13    5   12   15                                                  
CONECT   14    9   15                                                       
CONECT   15   13   14                                                       
CONECT   16   10                                                            
CONECT   17    4   19   20                                                  
CONECT   18    6    7   12                                                  
CONECT   19   17   22                                                       
CONECT   20   17   21                                                       
CONECT   21    1   20   23                                                  
CONECT   22    2   19   23                                                  
CONECT   23    3   21   22                                                  
CONECT   24    5    6    8                                                  
CONECT   25    1                                                            
CONECT   26    2                                                            
CONECT   27    3                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   58    0
END

COMPND    HMDB0015288
HETATM    1  C1  UNL     1      -4.949  -2.477  -2.234  1.00  0.00           C  
HETATM    2  O1  UNL     1      -5.322  -1.313  -1.520  1.00  0.00           O  
HETATM    3  C2  UNL     1      -4.321  -0.596  -0.892  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.978  -0.989  -0.946  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.990  -0.273  -0.320  1.00  0.00           C  
HETATM    6  N1  UNL     1      -0.618  -0.735  -0.417  1.00  0.00           N  
HETATM    7  C5  UNL     1       0.435  -0.006   0.227  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.754  -0.588   0.037  1.00  0.00           C  
HETATM    9  C7  UNL     1       1.968  -1.714  -0.686  1.00  0.00           C  
HETATM   10  C8  UNL     1       3.259  -2.234  -0.838  1.00  0.00           C  
HETATM   11  C9  UNL     1       4.333  -1.622  -0.263  1.00  0.00           C  
HETATM   12  N2  UNL     1       5.580  -2.131  -0.411  1.00  0.00           N  
HETATM   13  C10 UNL     1       6.633  -1.536   0.152  1.00  0.00           C  
HETATM   14  N3  UNL     1       7.964  -2.082  -0.009  1.00  0.00           N  
HETATM   15  N4  UNL     1       6.430  -0.432   0.863  1.00  0.00           N  
HETATM   16  C11 UNL     1       5.202   0.120   1.043  1.00  0.00           C  
HETATM   17  N5  UNL     1       5.101   1.300   1.823  1.00  0.00           N  
HETATM   18  C12 UNL     1       4.104  -0.461   0.483  1.00  0.00           C  
HETATM   19  C13 UNL     1       2.853   0.078   0.653  1.00  0.00           C  
HETATM   20  C14 UNL     1       2.601   1.305   1.439  1.00  0.00           C  
HETATM   21  C15 UNL     1      -2.330   0.862   0.380  1.00  0.00           C  
HETATM   22  C16 UNL     1      -3.650   1.291   0.461  1.00  0.00           C  
HETATM   23  O2  UNL     1      -4.010   2.427   1.159  1.00  0.00           O  
HETATM   24  C17 UNL     1      -2.982   3.165   1.805  1.00  0.00           C  
HETATM   25  C18 UNL     1      -4.632   0.563  -0.171  1.00  0.00           C  
HETATM   26  O3  UNL     1      -5.936   0.979  -0.096  1.00  0.00           O  
HETATM   27  C19 UNL     1      -6.536   1.863  -1.024  1.00  0.00           C  
HETATM   28  H1  UNL     1      -4.213  -2.225  -3.027  1.00  0.00           H  
HETATM   29  H2  UNL     1      -4.479  -3.180  -1.492  1.00  0.00           H  
HETATM   30  H3  UNL     1      -5.823  -3.011  -2.653  1.00  0.00           H  
HETATM   31  H4  UNL     1      -2.726  -1.887  -1.503  1.00  0.00           H  
HETATM   32  H5  UNL     1      -0.412  -1.591  -0.951  1.00  0.00           H  
HETATM   33  H6  UNL     1       0.354   1.034  -0.218  1.00  0.00           H  
HETATM   34  H7  UNL     1       0.269   0.036   1.345  1.00  0.00           H  
HETATM   35  H8  UNL     1       1.203  -2.279  -1.184  1.00  0.00           H  
HETATM   36  H9  UNL     1       3.435  -3.134  -1.416  1.00  0.00           H  
HETATM   37  H10 UNL     1       8.311  -2.373  -0.944  1.00  0.00           H  
HETATM   38  H11 UNL     1       8.552  -2.172   0.846  1.00  0.00           H  
HETATM   39  H12 UNL     1       4.816   1.256   2.800  1.00  0.00           H  
HETATM   40  H13 UNL     1       5.347   2.213   1.393  1.00  0.00           H  
HETATM   41  H14 UNL     1       1.504   1.571   1.266  1.00  0.00           H  
HETATM   42  H15 UNL     1       3.112   2.203   1.108  1.00  0.00           H  
HETATM   43  H16 UNL     1       2.587   1.127   2.549  1.00  0.00           H  
HETATM   44  H17 UNL     1      -1.571   1.444   0.881  1.00  0.00           H  
HETATM   45  H18 UNL     1      -2.232   3.543   1.106  1.00  0.00           H  
HETATM   46  H19 UNL     1      -3.424   3.971   2.452  1.00  0.00           H  
HETATM   47  H20 UNL     1      -2.487   2.460   2.535  1.00  0.00           H  
HETATM   48  H21 UNL     1      -7.546   2.138  -0.690  1.00  0.00           H  
HETATM   49  H22 UNL     1      -6.646   1.341  -2.001  1.00  0.00           H  
HETATM   50  H23 UNL     1      -5.892   2.753  -1.191  1.00  0.00           H  
CONECT    1    2   28   29   30
CONECT    2    3
CONECT    3    4    4   25
CONECT    4    5   31
CONECT    5    6   21   21
CONECT    6    7   32
CONECT    7    8   33   34
CONECT    8    9    9   19
CONECT    9   10   35
CONECT   10   11   11   36
CONECT   11   12   18
CONECT   12   13   13
CONECT   13   14   15
CONECT   14   37   38
CONECT   15   16   16
CONECT   16   17   18
CONECT   17   39   40
CONECT   18   19   19
CONECT   19   20
CONECT   20   41   42   43
CONECT   21   22   44
CONECT   22   23   25   25
CONECT   23   24
CONECT   24   45   46   47
CONECT   25   26
CONECT   26   27
CONECT   27   48   49   50
END

HMDB0015288
     RDKit          3D
Trimetrexate
 50 52  0  0  0  0  0  0  0  0999 V2000
   -4.9490   -2.4766   -2.2337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3224   -1.3131   -1.5201 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3206   -0.5964   -0.8917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9778   -0.9894   -0.9463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9901   -0.2727   -0.3201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6181   -0.7354   -0.4166 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4354   -0.0062    0.2272 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7540   -0.5884    0.0369 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9680   -1.7136   -0.6862 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2585   -2.2338   -0.8380 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3328   -1.6224   -0.2627 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5801   -2.1314   -0.4113 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6333   -1.5359    0.1525 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9635   -2.0824   -0.0088 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4295   -0.4324    0.8628 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2018    0.1196    1.0433 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1011    1.3003    1.8234 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1035   -0.4607    0.4825 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8530    0.0784    0.6529 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6014    1.3045    1.4390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3300    0.8621    0.3796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6504    1.2906    0.4611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0100    2.4273    1.1591 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9821    3.1650    1.8054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6324    0.5630   -0.1715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9363    0.9788   -0.0958 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5362    1.8626   -1.0245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2128   -2.2249   -3.0275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4795   -3.1800   -1.4922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8233   -3.0115   -2.6532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7259   -1.8873   -1.5026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4116   -1.5911   -0.9508 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3543    1.0344   -0.2177 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2689    0.0364    1.3455 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2032   -2.2794   -1.1839 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4346   -3.1338   -1.4158 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3107   -2.3725   -0.9440 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5525   -2.1715    0.8456 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8163    1.2559    2.7996 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3475    2.2125    1.3925 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5039    1.5712    1.2664 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1124    2.2032    1.1084 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5872    1.1268    2.5494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5708    1.4435    0.8811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2325    3.5427    1.1064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4241    3.9713    2.4520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4868    2.4602    2.5350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5464    2.1382   -0.6900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6464    1.3412   -2.0009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8920    2.7534   -1.1906 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  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
  5 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 22 25  2  0
 25 26  1  0
 26 27  1  0
 25  3  1  0
 19  8  1  0
 18 11  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  4 31  1  0
  6 32  1  0
  7 33  1  0
  7 34  1  0
  9 35  1  0
 10 36  1  0
 14 37  1  0
 14 38  1  0
 17 39  1  0
 17 40  1  0
 20 41  1  0
 20 42  1  0
 20 43  1  0
 21 44  1  0
 24 45  1  0
 24 46  1  0
 24 47  1  0
 27 48  1  0
 27 49  1  0
 27 50  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Trimetrexic acid	Generator
Neutrexin	HMDB
TMQ	HMDB
TMX	HMDB
Monohydrate, monoacetate trimetrexate	HMDB
Trimetrexate ipsen brand	HMDB
Trimetrexate monohydrate, monoacetate	HMDB
JB 11	HMDB
Hydrate, trimetrexate	HMDB
Ipsen brand OF trimetrexate	HMDB
JB-11	HMDB
Trimetrexate hydrate	HMDB

Chemical Formula

C₁₉H₂₃N₅O₃

Average Molecular Weight

369.4176

Monoisotopic Molecular Weight

369.180089627

IUPAC Name

5-methyl-6-{[(3,4,5-trimethoxyphenyl)amino]methyl}quinazoline-2,4-diamine

Traditional Name

trimetrexate

CAS Registry Number

52128-35-5

SMILES

COC1=CC(NCC2=C(C)C3=C(C=C2)N=C(N)N=C3N)=CC(OC)=C1OC

InChI Identifier

InChI=1S/C19H23N5O3/c1-10-11(5-6-13-16(10)18(20)24-19(21)23-13)9-22-12-7-14(25-2)17(27-4)15(8-12)26-3/h5-8,22H,9H2,1-4H3,(H4,20,21,23,24)

InChI Key

NOYPYLRCIDNJJB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quinazolinamines. These are heterocyclic aromatic compounds containing a quianazoline moiety substituted by one or more amine groups.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazanaphthalenes

Sub Class

Benzodiazines

Direct Parent

Quinazolinamines

Alternative Parents

Substituents

Quinazolinamine
Methoxyaniline
Aminophenyl ether
Aniline or substituted anilines
Phenylalkylamine
Phenoxy compound
Methoxybenzene
Phenol ether
Anisole
Secondary aliphatic/aromatic amine
Alkyl aryl ether
Aralkylamine
Aminopyrimidine
Pyrimidine
Benzenoid
Imidolactam
Monocyclic benzene moiety
Heteroaromatic compound
Ether
Azacycle
Secondary amine
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Amine
Primary amine
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

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: HMDB0015288)

Source

Exogenous

Exogenous (HMDB: HMDB0015288)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	215 - 217 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.031 g/L	Not Available
LogP	2	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.031 g/L	ALOGPS
logP	2.36	ALOGPS
logP	2.28	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	17.04	ChemAxon
pKa (Strongest Basic)	7.54	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	117.54 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	107.7 m³·mol⁻¹	ChemAxon
Polarizability	40.24 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	189.099	31661259
DarkChem	[M-H]-	191.484	31661259
DeepCCS	[M+H]+	188.603	30932474
DeepCCS	[M-H]-	186.245	30932474
DeepCCS	[M-2H]-	220.35	30932474
DeepCCS	[M+Na]+	195.578	30932474
AllCCS	[M+H]+	190.7	32859911
AllCCS	[M+H-H2O]+	187.9	32859911
AllCCS	[M+NH4]+	193.3	32859911
AllCCS	[M+Na]+	194.0	32859911
AllCCS	[M-H]-	192.1	32859911
AllCCS	[M+Na-2H]-	192.1	32859911
AllCCS	[M+HCOO]-	192.4	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.	2.82 minutes	32390414
Predicted by Siyang on May 30, 2022	10.1722 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.54 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	61.0 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1083.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	185.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	124.0 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	57.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	297.3 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	347.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	527.9 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	155.1 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	772.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	211.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	266.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	433.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	404.2 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	91.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Trimetrexate	COC1=CC(NCC2=C(C)C3=C(C=C2)N=C(N)N=C3N)=CC(OC)=C1OC	4771.5	Standard polar	33892256
Trimetrexate	COC1=CC(NCC2=C(C)C3=C(C=C2)N=C(N)N=C3N)=CC(OC)=C1OC	3432.8	Standard non polar	33892256
Trimetrexate	COC1=CC(NCC2=C(C)C3=C(C=C2)N=C(N)N=C3N)=CC(OC)=C1OC	3703.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Trimetrexate,1TMS,isomer #1	COC1=CC(NCC2=CC=C3N=C(N[Si](C)(C)C)N=C(N)C3=C2C)=CC(OC)=C1OC	3661.3	Semi standard non polar	33892256
Trimetrexate,1TMS,isomer #1	COC1=CC(NCC2=CC=C3N=C(N[Si](C)(C)C)N=C(N)C3=C2C)=CC(OC)=C1OC	3368.0	Standard non polar	33892256
Trimetrexate,1TMS,isomer #1	COC1=CC(NCC2=CC=C3N=C(N[Si](C)(C)C)N=C(N)C3=C2C)=CC(OC)=C1OC	5134.2	Standard polar	33892256
Trimetrexate,1TMS,isomer #2	COC1=CC(NCC2=CC=C3N=C(N)N=C(N[Si](C)(C)C)C3=C2C)=CC(OC)=C1OC	3706.8	Semi standard non polar	33892256
Trimetrexate,1TMS,isomer #2	COC1=CC(NCC2=CC=C3N=C(N)N=C(N[Si](C)(C)C)C3=C2C)=CC(OC)=C1OC	3375.3	Standard non polar	33892256
Trimetrexate,1TMS,isomer #2	COC1=CC(NCC2=CC=C3N=C(N)N=C(N[Si](C)(C)C)C3=C2C)=CC(OC)=C1OC	5112.1	Standard polar	33892256
Trimetrexate,1TMS,isomer #3	COC1=CC(N(CC2=CC=C3N=C(N)N=C(N)C3=C2C)[Si](C)(C)C)=CC(OC)=C1OC	3604.7	Semi standard non polar	33892256
Trimetrexate,1TMS,isomer #3	COC1=CC(N(CC2=CC=C3N=C(N)N=C(N)C3=C2C)[Si](C)(C)C)=CC(OC)=C1OC	3356.9	Standard non polar	33892256
Trimetrexate,1TMS,isomer #3	COC1=CC(N(CC2=CC=C3N=C(N)N=C(N)C3=C2C)[Si](C)(C)C)=CC(OC)=C1OC	5209.0	Standard polar	33892256
Trimetrexate,2TMS,isomer #1	COC1=CC(NCC2=CC=C3N=C(N[Si](C)(C)C)N=C(N[Si](C)(C)C)C3=C2C)=CC(OC)=C1OC	3663.4	Semi standard non polar	33892256
Trimetrexate,2TMS,isomer #1	COC1=CC(NCC2=CC=C3N=C(N[Si](C)(C)C)N=C(N[Si](C)(C)C)C3=C2C)=CC(OC)=C1OC	3399.4	Standard non polar	33892256
Trimetrexate,2TMS,isomer #1	COC1=CC(NCC2=CC=C3N=C(N[Si](C)(C)C)N=C(N[Si](C)(C)C)C3=C2C)=CC(OC)=C1OC	4854.6	Standard polar	33892256
Trimetrexate,2TMS,isomer #2	COC1=CC(N(CC2=CC=C3N=C(N[Si](C)(C)C)N=C(N)C3=C2C)[Si](C)(C)C)=CC(OC)=C1OC	3505.5	Semi standard non polar	33892256
Trimetrexate,2TMS,isomer #2	COC1=CC(N(CC2=CC=C3N=C(N[Si](C)(C)C)N=C(N)C3=C2C)[Si](C)(C)C)=CC(OC)=C1OC	3307.7	Standard non polar	33892256
Trimetrexate,2TMS,isomer #2	COC1=CC(N(CC2=CC=C3N=C(N[Si](C)(C)C)N=C(N)C3=C2C)[Si](C)(C)C)=CC(OC)=C1OC	4707.8	Standard polar	33892256
Trimetrexate,2TMS,isomer #3	COC1=CC(NCC2=CC=C3N=C(N([Si](C)(C)C)[Si](C)(C)C)N=C(N)C3=C2C)=CC(OC)=C1OC	3562.7	Semi standard non polar	33892256
Trimetrexate,2TMS,isomer #3	COC1=CC(NCC2=CC=C3N=C(N([Si](C)(C)C)[Si](C)(C)C)N=C(N)C3=C2C)=CC(OC)=C1OC	3458.6	Standard non polar	33892256
Trimetrexate,2TMS,isomer #3	COC1=CC(NCC2=CC=C3N=C(N([Si](C)(C)C)[Si](C)(C)C)N=C(N)C3=C2C)=CC(OC)=C1OC	4780.1	Standard polar	33892256
Trimetrexate,2TMS,isomer #4	COC1=CC(N(CC2=CC=C3N=C(N)N=C(N[Si](C)(C)C)C3=C2C)[Si](C)(C)C)=CC(OC)=C1OC	3528.1	Semi standard non polar	33892256
Trimetrexate,2TMS,isomer #4	COC1=CC(N(CC2=CC=C3N=C(N)N=C(N[Si](C)(C)C)C3=C2C)[Si](C)(C)C)=CC(OC)=C1OC	3333.8	Standard non polar	33892256
Trimetrexate,2TMS,isomer #4	COC1=CC(N(CC2=CC=C3N=C(N)N=C(N[Si](C)(C)C)C3=C2C)[Si](C)(C)C)=CC(OC)=C1OC	4688.1	Standard polar	33892256
Trimetrexate,2TMS,isomer #5	COC1=CC(NCC2=CC=C3N=C(N)N=C(N([Si](C)(C)C)[Si](C)(C)C)C3=C2C)=CC(OC)=C1OC	3568.5	Semi standard non polar	33892256
Trimetrexate,2TMS,isomer #5	COC1=CC(NCC2=CC=C3N=C(N)N=C(N([Si](C)(C)C)[Si](C)(C)C)C3=C2C)=CC(OC)=C1OC	3467.5	Standard non polar	33892256
Trimetrexate,2TMS,isomer #5	COC1=CC(NCC2=CC=C3N=C(N)N=C(N([Si](C)(C)C)[Si](C)(C)C)C3=C2C)=CC(OC)=C1OC	4811.2	Standard polar	33892256
Trimetrexate,3TMS,isomer #1	COC1=CC(N(CC2=CC=C3N=C(N[Si](C)(C)C)N=C(N[Si](C)(C)C)C3=C2C)[Si](C)(C)C)=CC(OC)=C1OC	3454.0	Semi standard non polar	33892256
Trimetrexate,3TMS,isomer #1	COC1=CC(N(CC2=CC=C3N=C(N[Si](C)(C)C)N=C(N[Si](C)(C)C)C3=C2C)[Si](C)(C)C)=CC(OC)=C1OC	3268.8	Standard non polar	33892256
Trimetrexate,3TMS,isomer #1	COC1=CC(N(CC2=CC=C3N=C(N[Si](C)(C)C)N=C(N[Si](C)(C)C)C3=C2C)[Si](C)(C)C)=CC(OC)=C1OC	4483.7	Standard polar	33892256
Trimetrexate,3TMS,isomer #2	COC1=CC(NCC2=CC=C3N=C(N([Si](C)(C)C)[Si](C)(C)C)N=C(N[Si](C)(C)C)C3=C2C)=CC(OC)=C1OC	3553.3	Semi standard non polar	33892256
Trimetrexate,3TMS,isomer #2	COC1=CC(NCC2=CC=C3N=C(N([Si](C)(C)C)[Si](C)(C)C)N=C(N[Si](C)(C)C)C3=C2C)=CC(OC)=C1OC	3487.8	Standard non polar	33892256
Trimetrexate,3TMS,isomer #2	COC1=CC(NCC2=CC=C3N=C(N([Si](C)(C)C)[Si](C)(C)C)N=C(N[Si](C)(C)C)C3=C2C)=CC(OC)=C1OC	4429.4	Standard polar	33892256
Trimetrexate,3TMS,isomer #3	COC1=CC(NCC2=CC=C3N=C(N[Si](C)(C)C)N=C(N([Si](C)(C)C)[Si](C)(C)C)C3=C2C)=CC(OC)=C1OC	3558.5	Semi standard non polar	33892256
Trimetrexate,3TMS,isomer #3	COC1=CC(NCC2=CC=C3N=C(N[Si](C)(C)C)N=C(N([Si](C)(C)C)[Si](C)(C)C)C3=C2C)=CC(OC)=C1OC	3466.0	Standard non polar	33892256
Trimetrexate,3TMS,isomer #3	COC1=CC(NCC2=CC=C3N=C(N[Si](C)(C)C)N=C(N([Si](C)(C)C)[Si](C)(C)C)C3=C2C)=CC(OC)=C1OC	4485.3	Standard polar	33892256
Trimetrexate,3TMS,isomer #4	COC1=CC(N(CC2=CC=C3N=C(N([Si](C)(C)C)[Si](C)(C)C)N=C(N)C3=C2C)[Si](C)(C)C)=CC(OC)=C1OC	3417.0	Semi standard non polar	33892256
Trimetrexate,3TMS,isomer #4	COC1=CC(N(CC2=CC=C3N=C(N([Si](C)(C)C)[Si](C)(C)C)N=C(N)C3=C2C)[Si](C)(C)C)=CC(OC)=C1OC	3386.1	Standard non polar	33892256
Trimetrexate,3TMS,isomer #4	COC1=CC(N(CC2=CC=C3N=C(N([Si](C)(C)C)[Si](C)(C)C)N=C(N)C3=C2C)[Si](C)(C)C)=CC(OC)=C1OC	4432.4	Standard polar	33892256
Trimetrexate,3TMS,isomer #5	COC1=CC(N(CC2=CC=C3N=C(N)N=C(N([Si](C)(C)C)[Si](C)(C)C)C3=C2C)[Si](C)(C)C)=CC(OC)=C1OC	3412.7	Semi standard non polar	33892256
Trimetrexate,3TMS,isomer #5	COC1=CC(N(CC2=CC=C3N=C(N)N=C(N([Si](C)(C)C)[Si](C)(C)C)C3=C2C)[Si](C)(C)C)=CC(OC)=C1OC	3397.5	Standard non polar	33892256
Trimetrexate,3TMS,isomer #5	COC1=CC(N(CC2=CC=C3N=C(N)N=C(N([Si](C)(C)C)[Si](C)(C)C)C3=C2C)[Si](C)(C)C)=CC(OC)=C1OC	4472.5	Standard polar	33892256
Trimetrexate,4TMS,isomer #1	COC1=CC(N(CC2=CC=C3N=C(N([Si](C)(C)C)[Si](C)(C)C)N=C(N[Si](C)(C)C)C3=C2C)[Si](C)(C)C)=CC(OC)=C1OC	3410.2	Semi standard non polar	33892256
Trimetrexate,4TMS,isomer #1	COC1=CC(N(CC2=CC=C3N=C(N([Si](C)(C)C)[Si](C)(C)C)N=C(N[Si](C)(C)C)C3=C2C)[Si](C)(C)C)=CC(OC)=C1OC	3360.5	Standard non polar	33892256
Trimetrexate,4TMS,isomer #1	COC1=CC(N(CC2=CC=C3N=C(N([Si](C)(C)C)[Si](C)(C)C)N=C(N[Si](C)(C)C)C3=C2C)[Si](C)(C)C)=CC(OC)=C1OC	4143.7	Standard polar	33892256
Trimetrexate,4TMS,isomer #2	COC1=CC(N(CC2=CC=C3N=C(N[Si](C)(C)C)N=C(N([Si](C)(C)C)[Si](C)(C)C)C3=C2C)[Si](C)(C)C)=CC(OC)=C1OC	3408.9	Semi standard non polar	33892256
Trimetrexate,4TMS,isomer #2	COC1=CC(N(CC2=CC=C3N=C(N[Si](C)(C)C)N=C(N([Si](C)(C)C)[Si](C)(C)C)C3=C2C)[Si](C)(C)C)=CC(OC)=C1OC	3337.4	Standard non polar	33892256
Trimetrexate,4TMS,isomer #2	COC1=CC(N(CC2=CC=C3N=C(N[Si](C)(C)C)N=C(N([Si](C)(C)C)[Si](C)(C)C)C3=C2C)[Si](C)(C)C)=CC(OC)=C1OC	4191.7	Standard polar	33892256
Trimetrexate,4TMS,isomer #3	COC1=CC(NCC2=CC=C3N=C(N([Si](C)(C)C)[Si](C)(C)C)N=C(N([Si](C)(C)C)[Si](C)(C)C)C3=C2C)=CC(OC)=C1OC	3485.8	Semi standard non polar	33892256
Trimetrexate,4TMS,isomer #3	COC1=CC(NCC2=CC=C3N=C(N([Si](C)(C)C)[Si](C)(C)C)N=C(N([Si](C)(C)C)[Si](C)(C)C)C3=C2C)=CC(OC)=C1OC	3554.9	Standard non polar	33892256
Trimetrexate,4TMS,isomer #3	COC1=CC(NCC2=CC=C3N=C(N([Si](C)(C)C)[Si](C)(C)C)N=C(N([Si](C)(C)C)[Si](C)(C)C)C3=C2C)=CC(OC)=C1OC	4138.1	Standard polar	33892256
Trimetrexate,5TMS,isomer #1	COC1=CC(N(CC2=CC=C3N=C(N([Si](C)(C)C)[Si](C)(C)C)N=C(N([Si](C)(C)C)[Si](C)(C)C)C3=C2C)[Si](C)(C)C)=CC(OC)=C1OC	3416.5	Semi standard non polar	33892256
Trimetrexate,5TMS,isomer #1	COC1=CC(N(CC2=CC=C3N=C(N([Si](C)(C)C)[Si](C)(C)C)N=C(N([Si](C)(C)C)[Si](C)(C)C)C3=C2C)[Si](C)(C)C)=CC(OC)=C1OC	3440.4	Standard non polar	33892256
Trimetrexate,5TMS,isomer #1	COC1=CC(N(CC2=CC=C3N=C(N([Si](C)(C)C)[Si](C)(C)C)N=C(N([Si](C)(C)C)[Si](C)(C)C)C3=C2C)[Si](C)(C)C)=CC(OC)=C1OC	3890.8	Standard polar	33892256
Trimetrexate,1TBDMS,isomer #1	COC1=CC(NCC2=CC=C3N=C(N[Si](C)(C)C(C)(C)C)N=C(N)C3=C2C)=CC(OC)=C1OC	3818.1	Semi standard non polar	33892256
Trimetrexate,1TBDMS,isomer #1	COC1=CC(NCC2=CC=C3N=C(N[Si](C)(C)C(C)(C)C)N=C(N)C3=C2C)=CC(OC)=C1OC	3570.1	Standard non polar	33892256
Trimetrexate,1TBDMS,isomer #1	COC1=CC(NCC2=CC=C3N=C(N[Si](C)(C)C(C)(C)C)N=C(N)C3=C2C)=CC(OC)=C1OC	5025.9	Standard polar	33892256
Trimetrexate,1TBDMS,isomer #2	COC1=CC(NCC2=CC=C3N=C(N)N=C(N[Si](C)(C)C(C)(C)C)C3=C2C)=CC(OC)=C1OC	3884.1	Semi standard non polar	33892256
Trimetrexate,1TBDMS,isomer #2	COC1=CC(NCC2=CC=C3N=C(N)N=C(N[Si](C)(C)C(C)(C)C)C3=C2C)=CC(OC)=C1OC	3570.0	Standard non polar	33892256
Trimetrexate,1TBDMS,isomer #2	COC1=CC(NCC2=CC=C3N=C(N)N=C(N[Si](C)(C)C(C)(C)C)C3=C2C)=CC(OC)=C1OC	5029.1	Standard polar	33892256
Trimetrexate,1TBDMS,isomer #3	COC1=CC(N(CC2=CC=C3N=C(N)N=C(N)C3=C2C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC	3836.9	Semi standard non polar	33892256
Trimetrexate,1TBDMS,isomer #3	COC1=CC(N(CC2=CC=C3N=C(N)N=C(N)C3=C2C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC	3514.4	Standard non polar	33892256
Trimetrexate,1TBDMS,isomer #3	COC1=CC(N(CC2=CC=C3N=C(N)N=C(N)C3=C2C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC	5158.2	Standard polar	33892256
Trimetrexate,2TBDMS,isomer #1	COC1=CC(NCC2=CC=C3N=C(N[Si](C)(C)C(C)(C)C)N=C(N[Si](C)(C)C(C)(C)C)C3=C2C)=CC(OC)=C1OC	4021.6	Semi standard non polar	33892256
Trimetrexate,2TBDMS,isomer #1	COC1=CC(NCC2=CC=C3N=C(N[Si](C)(C)C(C)(C)C)N=C(N[Si](C)(C)C(C)(C)C)C3=C2C)=CC(OC)=C1OC	3796.1	Standard non polar	33892256
Trimetrexate,2TBDMS,isomer #1	COC1=CC(NCC2=CC=C3N=C(N[Si](C)(C)C(C)(C)C)N=C(N[Si](C)(C)C(C)(C)C)C3=C2C)=CC(OC)=C1OC	4767.0	Standard polar	33892256
Trimetrexate,2TBDMS,isomer #2	COC1=CC(N(CC2=CC=C3N=C(N[Si](C)(C)C(C)(C)C)N=C(N)C3=C2C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC	3830.2	Semi standard non polar	33892256
Trimetrexate,2TBDMS,isomer #2	COC1=CC(N(CC2=CC=C3N=C(N[Si](C)(C)C(C)(C)C)N=C(N)C3=C2C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC	3665.1	Standard non polar	33892256
Trimetrexate,2TBDMS,isomer #2	COC1=CC(N(CC2=CC=C3N=C(N[Si](C)(C)C(C)(C)C)N=C(N)C3=C2C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC	4679.3	Standard polar	33892256
Trimetrexate,2TBDMS,isomer #3	COC1=CC(NCC2=CC=C3N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C(N)C3=C2C)=CC(OC)=C1OC	3937.8	Semi standard non polar	33892256
Trimetrexate,2TBDMS,isomer #3	COC1=CC(NCC2=CC=C3N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C(N)C3=C2C)=CC(OC)=C1OC	3769.1	Standard non polar	33892256
Trimetrexate,2TBDMS,isomer #3	COC1=CC(NCC2=CC=C3N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C(N)C3=C2C)=CC(OC)=C1OC	4672.8	Standard polar	33892256
Trimetrexate,2TBDMS,isomer #4	COC1=CC(N(CC2=CC=C3N=C(N)N=C(N[Si](C)(C)C(C)(C)C)C3=C2C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC	3849.8	Semi standard non polar	33892256
Trimetrexate,2TBDMS,isomer #4	COC1=CC(N(CC2=CC=C3N=C(N)N=C(N[Si](C)(C)C(C)(C)C)C3=C2C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC	3685.6	Standard non polar	33892256
Trimetrexate,2TBDMS,isomer #4	COC1=CC(N(CC2=CC=C3N=C(N)N=C(N[Si](C)(C)C(C)(C)C)C3=C2C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC	4678.6	Standard polar	33892256
Trimetrexate,2TBDMS,isomer #5	COC1=CC(NCC2=CC=C3N=C(N)N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C3=C2C)=CC(OC)=C1OC	3959.3	Semi standard non polar	33892256
Trimetrexate,2TBDMS,isomer #5	COC1=CC(NCC2=CC=C3N=C(N)N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C3=C2C)=CC(OC)=C1OC	3783.3	Standard non polar	33892256
Trimetrexate,2TBDMS,isomer #5	COC1=CC(NCC2=CC=C3N=C(N)N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C3=C2C)=CC(OC)=C1OC	4728.1	Standard polar	33892256
Trimetrexate,3TBDMS,isomer #1	COC1=CC(N(CC2=CC=C3N=C(N[Si](C)(C)C(C)(C)C)N=C(N[Si](C)(C)C(C)(C)C)C3=C2C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC	3904.1	Semi standard non polar	33892256
Trimetrexate,3TBDMS,isomer #1	COC1=CC(N(CC2=CC=C3N=C(N[Si](C)(C)C(C)(C)C)N=C(N[Si](C)(C)C(C)(C)C)C3=C2C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC	3824.9	Standard non polar	33892256
Trimetrexate,3TBDMS,isomer #1	COC1=CC(N(CC2=CC=C3N=C(N[Si](C)(C)C(C)(C)C)N=C(N[Si](C)(C)C(C)(C)C)C3=C2C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC	4549.4	Standard polar	33892256
Trimetrexate,3TBDMS,isomer #2	COC1=CC(NCC2=CC=C3N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C(N[Si](C)(C)C(C)(C)C)C3=C2C)=CC(OC)=C1OC	4068.7	Semi standard non polar	33892256
Trimetrexate,3TBDMS,isomer #2	COC1=CC(NCC2=CC=C3N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C(N[Si](C)(C)C(C)(C)C)C3=C2C)=CC(OC)=C1OC	3991.9	Standard non polar	33892256
Trimetrexate,3TBDMS,isomer #2	COC1=CC(NCC2=CC=C3N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C(N[Si](C)(C)C(C)(C)C)C3=C2C)=CC(OC)=C1OC	4469.4	Standard polar	33892256
Trimetrexate,3TBDMS,isomer #3	COC1=CC(NCC2=CC=C3N=C(N[Si](C)(C)C(C)(C)C)N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C3=C2C)=CC(OC)=C1OC	4064.4	Semi standard non polar	33892256
Trimetrexate,3TBDMS,isomer #3	COC1=CC(NCC2=CC=C3N=C(N[Si](C)(C)C(C)(C)C)N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C3=C2C)=CC(OC)=C1OC	3975.7	Standard non polar	33892256
Trimetrexate,3TBDMS,isomer #3	COC1=CC(NCC2=CC=C3N=C(N[Si](C)(C)C(C)(C)C)N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C3=C2C)=CC(OC)=C1OC	4518.2	Standard polar	33892256
Trimetrexate,3TBDMS,isomer #4	COC1=CC(N(CC2=CC=C3N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C(N)C3=C2C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC	3960.8	Semi standard non polar	33892256
Trimetrexate,3TBDMS,isomer #4	COC1=CC(N(CC2=CC=C3N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C(N)C3=C2C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC	3836.3	Standard non polar	33892256
Trimetrexate,3TBDMS,isomer #4	COC1=CC(N(CC2=CC=C3N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C(N)C3=C2C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC	4477.6	Standard polar	33892256
Trimetrexate,3TBDMS,isomer #5	COC1=CC(N(CC2=CC=C3N=C(N)N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C3=C2C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC	3948.1	Semi standard non polar	33892256
Trimetrexate,3TBDMS,isomer #5	COC1=CC(N(CC2=CC=C3N=C(N)N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C3=C2C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC	3851.7	Standard non polar	33892256
Trimetrexate,3TBDMS,isomer #5	COC1=CC(N(CC2=CC=C3N=C(N)N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C3=C2C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC	4526.1	Standard polar	33892256
Trimetrexate,4TBDMS,isomer #1	COC1=CC(N(CC2=CC=C3N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C(N[Si](C)(C)C(C)(C)C)C3=C2C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC	4032.2	Semi standard non polar	33892256
Trimetrexate,4TBDMS,isomer #1	COC1=CC(N(CC2=CC=C3N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C(N[Si](C)(C)C(C)(C)C)C3=C2C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC	4032.6	Standard non polar	33892256
Trimetrexate,4TBDMS,isomer #1	COC1=CC(N(CC2=CC=C3N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C(N[Si](C)(C)C(C)(C)C)C3=C2C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC	4338.8	Standard polar	33892256
Trimetrexate,4TBDMS,isomer #2	COC1=CC(N(CC2=CC=C3N=C(N[Si](C)(C)C(C)(C)C)N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C3=C2C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC	4031.3	Semi standard non polar	33892256
Trimetrexate,4TBDMS,isomer #2	COC1=CC(N(CC2=CC=C3N=C(N[Si](C)(C)C(C)(C)C)N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C3=C2C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC	4017.8	Standard non polar	33892256
Trimetrexate,4TBDMS,isomer #2	COC1=CC(N(CC2=CC=C3N=C(N[Si](C)(C)C(C)(C)C)N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C3=C2C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC	4383.2	Standard polar	33892256
Trimetrexate,4TBDMS,isomer #3	COC1=CC(NCC2=CC=C3N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C3=C2C)=CC(OC)=C1OC	4129.9	Semi standard non polar	33892256
Trimetrexate,4TBDMS,isomer #3	COC1=CC(NCC2=CC=C3N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C3=C2C)=CC(OC)=C1OC	4173.1	Standard non polar	33892256
Trimetrexate,4TBDMS,isomer #3	COC1=CC(NCC2=CC=C3N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C3=C2C)=CC(OC)=C1OC	4293.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Trimetrexate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ugj-0409000000-97a2080cda5a33464953	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Trimetrexate 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trimetrexate 10V, Positive-QTOF	splash10-00dr-0409000000-a9fcda741827d39a85bc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trimetrexate 20V, Positive-QTOF	splash10-000i-0903000000-d3e9f90709b809eb4f3d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trimetrexate 40V, Positive-QTOF	splash10-000i-2911000000-97342eb0d2ab1fad8f13	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trimetrexate 10V, Negative-QTOF	splash10-014i-0209000000-e610f7928dd8d57d924c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trimetrexate 20V, Negative-QTOF	splash10-014i-0209000000-c28a10a57fcb7298832a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trimetrexate 40V, Negative-QTOF	splash10-00kf-9431000000-249d2de16520a2966585	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trimetrexate 10V, Positive-QTOF	splash10-00di-0109000000-a0632a23538eb5952dd1	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trimetrexate 20V, Positive-QTOF	splash10-00di-0309000000-95e446c0693d174b1b3e	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trimetrexate 40V, Positive-QTOF	splash10-000i-0930000000-a03a19d017251496a0fb	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trimetrexate 10V, Negative-QTOF	splash10-014i-0009000000-f667390d4352ff65f24d	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trimetrexate 20V, Negative-QTOF	splash10-0gbi-0129000000-24c353e7a0c027954a2a	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trimetrexate 40V, Negative-QTOF	splash10-00vj-2493000000-41a8bf8d77660b776bda	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

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 DB01157	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01157	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01157

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5381

KEGG Compound ID

C11154

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Trimetrexate

METLIN ID

Not Available

PubChem Compound

5583

PDB ID

Not Available

ChEBI ID

119101

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)

Not Available

General References

Not Available

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

Bertino JR, Zhao SC, Mineishi S, Ercikan-Abali EA, Banerjee D: Use of variants of dihydrofolate reductase in gene transfer to produce resistance to methotrexate and trimetrexate. Prog Exp Tumor Res. 1999;36:82-94. [PubMed:10386066 ]
Graffner-Nordberg M, Kolmodin K, Aqvist J, Queener SF, Hallberg A: Design, synthesis, computational prediction, and biological evaluation of ester soft drugs as inhibitors of dihydrofolate reductase from Pneumocystis carinii. J Med Chem. 2001 Jul 19;44(15):2391-402. [PubMed:11448221 ]
Warlick CA, Diers MD, Wagner JE, McIvor RS: In vivo selection of antifolate-resistant transgenic hematopoietic stem cells in a murine bone marrow transplant model. J Pharmacol Exp Ther. 2002 Jan;300(1):50-6. [PubMed:11752096 ]
Zhu WY, Bunni M, Priest DG, DiCapua JL, Dressler JM, Chen Z, Melera PW: Severe folate restriction results in depletion of and alteration in the composition of the intracellular folate pool, moderate sensitization to methotrexate and trimetrexate, upregulation of endogenous DHFR activity, and overexpression of metallothionein II and folate receptor alpha that, upon folate repletion, confer drug resistance to CHL cells. J Exp Ther Oncol. 2002 Sep-Oct;2(5):264-77. [PubMed:12416030 ]
Sweeney CL, Frandsen JL, Verfaillie CM, McIvor RS: Trimetrexate inhibits progression of the murine 32Dp210 model of chronic myeloid leukemia in animals expressing drug-resistant dihydrofolate reductase. Cancer Res. 2003 Mar 15;63(6):1304-10. [PubMed:12649191 ]
Polshakov VI, Birdsall B, Frenkiel TA, Gargaro AR, Feeney J: Structure and dynamics in solution of the complex of Lactobacillus casei dihydrofolate reductase with the new lipophilic antifolate drug trimetrexate. Protein Sci. 1999 Mar;8(3):467-81. [PubMed:10091649 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Showing metabocard for Trimetrexate (HMDB0015288)

MOL for HMDB0015288 (Trimetrexate)

3D MOL for HMDB0015288 (Trimetrexate)

3D SDF for HMDB0015288 (Trimetrexate)

3D-SDF for HMDB0015288 (Trimetrexate)

PDB for HMDB0015288 (Trimetrexate)

3D PDB for HMDB0015288 (Trimetrexate)

SMILES for HMDB0015288 (Trimetrexate)

INCHI for HMDB0015288 (Trimetrexate)

Structure for HMDB0015288 (Trimetrexate)

3D Structure for HMDB0015288 (Trimetrexate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References