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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:37 UTC

HMDB ID

HMDB0014438

Secondary Accession Numbers

HMDB14438

Metabolite Identification

Common Name

Raltitrexed

Description

Raltitrexed, also known as tomudex or ZD1694, belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Raltitrexed is a drug which is used for the treatment of malignant neoplasm of colon and rectum. Raltitrexed is fully active after polyglutamylation, which allows cellular retention of the drug. Raltitrexed is an extremely weak basic (essentially neutral) compound (based on its pKa). Inhibition of L1210 cell growth in culture IC50 9 nM, is one of the strongest antimetabolites in use. By inhibiting Thymidylate synthase (TS), thus formation of precursor pyrimidine nucleotides, raltitrexed prevents the formation of DNA and RNA, which are required for the growth and survival of both normal cells and cancer cells. Raltitrexed is approved for use in Canada and some European countries, but is not approved by the US FDA.Raltitrexed is chemically similar to folic acid and is in the class of chemotherapy drugs called folate antimetabolites, which inhibit one or more of three enzymes that use folate and derivatives as substrates: DHFR, GARFT and thymidylate synthase. Structure and phase I clinical trial of the precursor drug, CB3717, was described in 1986. Used in treatment of colorectal cancer since 1998, it may also be used in the treatment of malignant mesothelioma. Raltitrexed (Tomudex, TDX, ZD 1694) is an antimetabolite drug used in cancer chemotherapy. It is an inhibitor of thymidylate synthase, and is manufactured by AstraZeneca.

Structure

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

293
  Mrv0541 02231214342D          

 32 34  0  0  1  0            999 V2000
    8.1753    0.3429    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   12.1522   -1.3618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8843    0.5632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9929   -2.1972    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -0.7894    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1676    0.8954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8644    1.4816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7074    0.4255    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0282   -0.8586    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    1.6857    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4481    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9914    0.0158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8490   -0.7755    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2785    0.4310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1874   -0.0231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4203    0.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.4481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5310    0.0071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.2732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0083    0.0600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2785    1.2903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7250   -0.2723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5310    1.7143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5458   -0.1893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7107    1.2505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5034   -0.8106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3097   -0.9852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3313   -1.4448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    0.0356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.2732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3467    0.8123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.6857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 16  1  0  0  0  0
  1 22  1  0  0  0  0
  2 28  1  0  0  0  0
  3 24  2  0  0  0  0
  4 28  2  0  0  0  0
  5 29  2  0  0  0  0
  6 31  1  0  0  0  0
  7 31  2  0  0  0  0
  8 12  1  0  0  0  0
  8 16  1  0  0  0  0
  8 25  1  0  0  0  0
 13  9  1  1  0  0  0
  9 24  1  0  0  0  0
 10 19  1  0  0  0  0
 10 30  1  0  0  0  0
 11 29  1  0  0  0  0
 11 30  2  0  0  0  0
 12 14  1  0  0  0  0
 13 15  1  0  0  0  0
 13 28  1  0  0  0  0
 14 18  2  0  0  0  0
 14 21  1  0  0  0  0
 15 20  1  0  0  0  0
 16 26  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 17 29  1  0  0  0  0
 19 23  1  0  0  0  0
 20 31  1  0  0  0  0
 21 23  2  0  0  0  0
 22 24  1  0  0  0  0
 22 27  2  0  0  0  0
 26 27  1  0  0  0  0
 30 32  1  0  0  0  0
M  END

HMDB0014438
     RDKit          3D
Raltitrexed
 54 56  0  0  0  0  0  0  0  0999 V2000
    9.9558    0.2123    0.6288 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5252   -0.0463    0.2708 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0204    0.2182   -0.9549 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7328    0.0125   -1.2681 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2590    0.2593   -2.4066 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8413   -0.4942   -0.3169 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5110   -0.6894   -0.5968 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6268   -1.1629    0.3483 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1719   -1.3239    0.0497 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4752   -0.0982    0.2404 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1575    1.1648    0.4495 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0659   -0.0054    0.2044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7611    0.1609   -0.8834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0701    0.3221   -0.6539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4894    0.3109    0.6412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8823    0.5560    1.1592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9624    0.5149    2.4098 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9113    0.8149    0.2995 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9552    1.0772   -0.5629 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.6205   -0.1182   -1.1584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2001   -1.1160   -0.2451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2944   -0.7485    0.6474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8730    0.3370    0.6900 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7351   -1.7631    1.5655 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9371    2.0942   -0.1629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8809    2.6200    0.9792 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9345    2.4950   -1.0448 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0599    0.0687    1.5159 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.1161   -1.4402    1.5994 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4777   -1.2383    1.8815 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3636   -0.7600    0.9258 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6628   -0.5366    1.1888 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9737    0.8624    1.5583 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3785    0.8557   -0.1680 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5188   -0.6782    0.8807 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1130   -0.4716   -1.5931 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0731   -1.6625   -1.0148 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7029   -2.1047    0.6809 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2343    1.1423    0.3607 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7871    1.9155   -0.2908 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9053    1.4796    1.4898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3334    0.1569   -1.9146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8332    0.4639   -1.4629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7621    0.9071    1.3676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5079    1.6194   -1.5286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4667    0.2656   -1.8126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9346   -0.6115   -1.9148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4116   -1.5996    0.4116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6002   -1.9594   -0.8973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0252   -1.4584    2.4899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6201    3.1961   -0.7613 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4904   -1.8125    2.3999 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8744   -1.4582    2.8691 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0478   -0.7458    2.1535 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 19 25  1  0
 25 26  2  0
 25 27  1  0
 15 28  1  0
  8 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32  2  1  0
 31  6  1  0
 28 12  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  7 36  1  0
  9 37  1  0
  9 38  1  0
 11 39  1  0
 11 40  1  0
 11 41  1  0
 13 42  1  0
 14 43  1  0
 18 44  1  0
 19 45  1  6
 20 46  1  0
 20 47  1  0
 21 48  1  0
 21 49  1  0
 24 50  1  0
 27 51  1  0
 29 52  1  0
 30 53  1  0
 32 54  1  0
M  END

293
  Mrv0541 02231214342D          

 32 34  0  0  1  0            999 V2000
    8.1753    0.3429    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   12.1522   -1.3618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8843    0.5632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9929   -2.1972    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -0.7894    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1676    0.8954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8644    1.4816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7074    0.4255    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0282   -0.8586    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    1.6857    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4481    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9914    0.0158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8490   -0.7755    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2785    0.4310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1874   -0.0231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4203    0.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.4481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5310    0.0071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.2732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0083    0.0600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2785    1.2903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7250   -0.2723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5310    1.7143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5458   -0.1893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7107    1.2505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5034   -0.8106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3097   -0.9852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3313   -1.4448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    0.0356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.2732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3467    0.8123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.6857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 16  1  0  0  0  0
  1 22  1  0  0  0  0
  2 28  1  0  0  0  0
  3 24  2  0  0  0  0
  4 28  2  0  0  0  0
  5 29  2  0  0  0  0
  6 31  1  0  0  0  0
  7 31  2  0  0  0  0
  8 12  1  0  0  0  0
  8 16  1  0  0  0  0
  8 25  1  0  0  0  0
 13  9  1  1  0  0  0
  9 24  1  0  0  0  0
 10 19  1  0  0  0  0
 10 30  1  0  0  0  0
 11 29  1  0  0  0  0
 11 30  2  0  0  0  0
 12 14  1  0  0  0  0
 13 15  1  0  0  0  0
 13 28  1  0  0  0  0
 14 18  2  0  0  0  0
 14 21  1  0  0  0  0
 15 20  1  0  0  0  0
 16 26  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 17 29  1  0  0  0  0
 19 23  1  0  0  0  0
 20 31  1  0  0  0  0
 21 23  2  0  0  0  0
 22 24  1  0  0  0  0
 22 27  2  0  0  0  0
 26 27  1  0  0  0  0
 30 32  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014438

> <DATABASE_NAME>
hmdb

> <SMILES>
CN(CC1=CC2=C(NC(C)=NC2=O)C=C1)C1=CC=C(S1)C(=O)N[C@@H](CCC(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C21H22N4O6S/c1-11-22-14-4-3-12(9-13(14)19(28)23-11)10-25(2)17-7-6-16(32-17)20(29)24-15(21(30)31)5-8-18(26)27/h3-4,6-7,9,15H,5,8,10H2,1-2H3,(H,24,29)(H,26,27)(H,30,31)(H,22,23,28)/t15-/m0/s1

> <INCHI_KEY>
IVTVGDXNLFLDRM-HNNXBMFYSA-N

> <FORMULA>
C21H22N4O6S

> <MOLECULAR_WEIGHT>
458.488

> <EXACT_MASS>
458.126005146

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
45.554454906958014

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-2-[(5-{methyl[(2-methyl-4-oxo-1,4-dihydroquinazolin-6-yl)methyl]amino}thiophen-2-yl)formamido]pentanedioic acid

> <ALOGPS_LOGP>
1.65

> <JCHEM_LOGP>
1.970358828333333

> <ALOGPS_LOGS>
-4.40

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.448657561305654

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.7238410806930564

> <JCHEM_PKA_STRONGEST_BASIC>
-0.4573108487877974

> <JCHEM_POLAR_SURFACE_AREA>
148.39999999999998

> <JCHEM_REFRACTIVITY>
117.39150000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.81e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
raltitrexed

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014438
     RDKit          3D
Raltitrexed
 54 56  0  0  0  0  0  0  0  0999 V2000
    9.9558    0.2123    0.6288 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5252   -0.0463    0.2708 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0204    0.2182   -0.9549 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7328    0.0125   -1.2681 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2590    0.2593   -2.4066 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8413   -0.4942   -0.3169 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5110   -0.6894   -0.5968 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6268   -1.1629    0.3483 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1719   -1.3239    0.0497 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4752   -0.0982    0.2404 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1575    1.1648    0.4495 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0659   -0.0054    0.2044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7611    0.1609   -0.8834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0701    0.3221   -0.6539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4894    0.3109    0.6412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8823    0.5560    1.1592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9624    0.5149    2.4098 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9113    0.8149    0.2995 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9552    1.0772   -0.5629 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.6205   -0.1182   -1.1584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2001   -1.1160   -0.2451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2944   -0.7485    0.6474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8730    0.3370    0.6900 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7351   -1.7631    1.5655 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9371    2.0942   -0.1629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8809    2.6200    0.9792 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9345    2.4950   -1.0448 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0599    0.0687    1.5159 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.1161   -1.4402    1.5994 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4777   -1.2383    1.8815 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3636   -0.7600    0.9258 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6628   -0.5366    1.1888 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9737    0.8624    1.5583 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3785    0.8557   -0.1680 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5188   -0.6782    0.8807 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1130   -0.4716   -1.5931 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0731   -1.6625   -1.0148 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7029   -2.1047    0.6809 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2343    1.1423    0.3607 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7871    1.9155   -0.2908 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9053    1.4796    1.4898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3334    0.1569   -1.9146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8332    0.4639   -1.4629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7621    0.9071    1.3676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5079    1.6194   -1.5286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4667    0.2656   -1.8126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9346   -0.6115   -1.9148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4116   -1.5996    0.4116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6002   -1.9594   -0.8973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0252   -1.4584    2.4899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6201    3.1961   -0.7613 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4904   -1.8125    2.3999 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8744   -1.4582    2.8691 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0478   -0.7458    2.1535 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 19 25  1  0
 25 26  2  0
 25 27  1  0
 15 28  1  0
  8 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32  2  1  0
 31  6  1  0
 28 12  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  7 36  1  0
  9 37  1  0
  9 38  1  0
 11 39  1  0
 11 40  1  0
 11 41  1  0
 13 42  1  0
 14 43  1  0
 18 44  1  0
 19 45  1  6
 20 46  1  0
 20 47  1  0
 21 48  1  0
 21 49  1  0
 24 50  1  0
 27 51  1  0
 29 52  1  0
 30 53  1  0
 32 54  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 293                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0      15.261   0.640   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0      22.684  -2.542   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      18.451   1.051   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      20.520  -4.101   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       5.747  -1.474   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      24.580   1.671   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      22.147   2.766   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0      12.520   0.794   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0      18.719  -1.603   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0       5.747   3.147   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0       4.414   0.836   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      11.184   0.029   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      20.251  -1.448   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.853   0.805   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      20.883  -0.043   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.851   0.019   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.081   0.836   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.458   0.013   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.081   2.377   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      22.415   0.112   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.853   2.409   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      16.287  -0.508   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.458   3.200   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      17.819  -0.353   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      12.527   2.334   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      14.006  -1.513   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      15.511  -1.839   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      21.152  -2.697   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.747   0.066   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.414   2.377   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      23.047   1.516   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.080   3.147   0.000  0.00  0.00           C+0
CONECT    1   16   22                                                       
CONECT    2   28                                                            
CONECT    3   24                                                            
CONECT    4   28                                                            
CONECT    5   29                                                            
CONECT    6   31                                                            
CONECT    7   31                                                            
CONECT    8   12   16   25                                                  
CONECT    9   13   24                                                       
CONECT   10   19   30                                                       
CONECT   11   29   30                                                       
CONECT   12    8   14                                                       
CONECT   13    9   15   28                                                  
CONECT   14   12   18   21                                                  
CONECT   15   13   20                                                       
CONECT   16    1    8   26                                                  
CONECT   17   18   19   29                                                  
CONECT   18   14   17                                                       
CONECT   19   10   17   23                                                  
CONECT   20   15   31                                                       
CONECT   21   14   23                                                       
CONECT   22    1   24   27                                                  
CONECT   23   19   21                                                       
CONECT   24    3    9   22                                                  
CONECT   25    8                                                            
CONECT   26   16   27                                                       
CONECT   27   22   26                                                       
CONECT   28    2    4   13                                                  
CONECT   29    5   11   17                                                  
CONECT   30   10   11   32                                                  
CONECT   31    6    7   20                                                  
CONECT   32   30                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   68    0
END

COMPND    HMDB0014438
HETATM    1  C1  UNL     1       9.956   0.212   0.629  1.00  0.00           C  
HETATM    2  C2  UNL     1       8.525  -0.046   0.271  1.00  0.00           C  
HETATM    3  N1  UNL     1       8.020   0.218  -0.955  1.00  0.00           N  
HETATM    4  C3  UNL     1       6.733   0.013  -1.268  1.00  0.00           C  
HETATM    5  O1  UNL     1       6.259   0.259  -2.407  1.00  0.00           O  
HETATM    6  C4  UNL     1       5.841  -0.494  -0.317  1.00  0.00           C  
HETATM    7  C5  UNL     1       4.511  -0.689  -0.597  1.00  0.00           C  
HETATM    8  C6  UNL     1       3.627  -1.163   0.348  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.172  -1.324   0.050  1.00  0.00           C  
HETATM   10  N2  UNL     1       1.475  -0.098   0.240  1.00  0.00           N  
HETATM   11  C8  UNL     1       2.158   1.165   0.450  1.00  0.00           C  
HETATM   12  C9  UNL     1       0.066  -0.005   0.204  1.00  0.00           C  
HETATM   13  C10 UNL     1      -0.761   0.161  -0.883  1.00  0.00           C  
HETATM   14  C11 UNL     1      -2.070   0.322  -0.654  1.00  0.00           C  
HETATM   15  C12 UNL     1      -2.489   0.311   0.641  1.00  0.00           C  
HETATM   16  C13 UNL     1      -3.882   0.556   1.159  1.00  0.00           C  
HETATM   17  O2  UNL     1      -3.962   0.515   2.410  1.00  0.00           O  
HETATM   18  N3  UNL     1      -4.911   0.815   0.300  1.00  0.00           N  
HETATM   19  C14 UNL     1      -5.955   1.077  -0.563  1.00  0.00           C  
HETATM   20  C15 UNL     1      -6.621  -0.118  -1.158  1.00  0.00           C  
HETATM   21  C16 UNL     1      -7.200  -1.116  -0.245  1.00  0.00           C  
HETATM   22  C17 UNL     1      -8.294  -0.748   0.647  1.00  0.00           C  
HETATM   23  O3  UNL     1      -8.873   0.337   0.690  1.00  0.00           O  
HETATM   24  O4  UNL     1      -8.735  -1.763   1.566  1.00  0.00           O  
HETATM   25  C18 UNL     1      -6.937   2.094  -0.163  1.00  0.00           C  
HETATM   26  O5  UNL     1      -6.881   2.620   0.979  1.00  0.00           O  
HETATM   27  O6  UNL     1      -7.934   2.495  -1.045  1.00  0.00           O  
HETATM   28  S1  UNL     1      -1.060   0.069   1.516  1.00  0.00           S  
HETATM   29  C19 UNL     1       4.116  -1.440   1.599  1.00  0.00           C  
HETATM   30  C20 UNL     1       5.478  -1.238   1.882  1.00  0.00           C  
HETATM   31  C21 UNL     1       6.364  -0.760   0.926  1.00  0.00           C  
HETATM   32  N4  UNL     1       7.663  -0.537   1.189  1.00  0.00           N  
HETATM   33  H1  UNL     1       9.974   0.862   1.558  1.00  0.00           H  
HETATM   34  H2  UNL     1      10.378   0.856  -0.168  1.00  0.00           H  
HETATM   35  H3  UNL     1      10.519  -0.678   0.881  1.00  0.00           H  
HETATM   36  H4  UNL     1       4.113  -0.472  -1.593  1.00  0.00           H  
HETATM   37  H5  UNL     1       2.073  -1.662  -1.015  1.00  0.00           H  
HETATM   38  H6  UNL     1       1.703  -2.105   0.681  1.00  0.00           H  
HETATM   39  H7  UNL     1       3.234   1.142   0.361  1.00  0.00           H  
HETATM   40  H8  UNL     1       1.787   1.915  -0.291  1.00  0.00           H  
HETATM   41  H9  UNL     1       1.905   1.480   1.490  1.00  0.00           H  
HETATM   42  H10 UNL     1      -0.333   0.157  -1.915  1.00  0.00           H  
HETATM   43  H11 UNL     1      -2.833   0.464  -1.463  1.00  0.00           H  
HETATM   44  H12 UNL     1      -5.762   0.907   1.368  1.00  0.00           H  
HETATM   45  H13 UNL     1      -5.508   1.619  -1.529  1.00  0.00           H  
HETATM   46  H14 UNL     1      -7.467   0.266  -1.813  1.00  0.00           H  
HETATM   47  H15 UNL     1      -5.935  -0.612  -1.915  1.00  0.00           H  
HETATM   48  H16 UNL     1      -6.412  -1.600   0.412  1.00  0.00           H  
HETATM   49  H17 UNL     1      -7.600  -1.959  -0.897  1.00  0.00           H  
HETATM   50  H18 UNL     1      -9.025  -1.458   2.490  1.00  0.00           H  
HETATM   51  H19 UNL     1      -8.620   3.196  -0.761  1.00  0.00           H  
HETATM   52  H20 UNL     1       3.490  -1.812   2.400  1.00  0.00           H  
HETATM   53  H21 UNL     1       5.874  -1.458   2.869  1.00  0.00           H  
HETATM   54  H22 UNL     1       8.048  -0.746   2.154  1.00  0.00           H  
CONECT    1    2   33   34   35
CONECT    2    3    3   32
CONECT    3    4
CONECT    4    5    5    6
CONECT    6    7    7   31
CONECT    7    8   36
CONECT    8    9   29   29
CONECT    9   10   37   38
CONECT   10   11   12
CONECT   11   39   40   41
CONECT   12   13   13   28
CONECT   13   14   42
CONECT   14   15   15   43
CONECT   15   16   28
CONECT   16   17   17   18
CONECT   18   19   44
CONECT   19   20   25   45
CONECT   20   21   46   47
CONECT   21   22   48   49
CONECT   22   23   23   24
CONECT   24   50
CONECT   25   26   26   27
CONECT   27   51
CONECT   29   30   52
CONECT   30   31   31   53
CONECT   31   32
CONECT   32   54
END

HMDB0014438
     RDKit          3D
Raltitrexed
 54 56  0  0  0  0  0  0  0  0999 V2000
    9.9558    0.2123    0.6288 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5252   -0.0463    0.2708 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0204    0.2182   -0.9549 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7328    0.0125   -1.2681 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2590    0.2593   -2.4066 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8413   -0.4942   -0.3169 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5110   -0.6894   -0.5968 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6268   -1.1629    0.3483 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1719   -1.3239    0.0497 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4752   -0.0982    0.2404 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1575    1.1648    0.4495 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0659   -0.0054    0.2044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7611    0.1609   -0.8834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0701    0.3221   -0.6539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4894    0.3109    0.6412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8823    0.5560    1.1592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9624    0.5149    2.4098 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9113    0.8149    0.2995 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9552    1.0772   -0.5629 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.6205   -0.1182   -1.1584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2001   -1.1160   -0.2451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2944   -0.7485    0.6474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8730    0.3370    0.6900 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7351   -1.7631    1.5655 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9371    2.0942   -0.1629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8809    2.6200    0.9792 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9345    2.4950   -1.0448 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0599    0.0687    1.5159 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.1161   -1.4402    1.5994 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4777   -1.2383    1.8815 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3636   -0.7600    0.9258 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6628   -0.5366    1.1888 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9737    0.8624    1.5583 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3785    0.8557   -0.1680 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5188   -0.6782    0.8807 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1130   -0.4716   -1.5931 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0731   -1.6625   -1.0148 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7029   -2.1047    0.6809 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2343    1.1423    0.3607 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7871    1.9155   -0.2908 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9053    1.4796    1.4898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3334    0.1569   -1.9146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8332    0.4639   -1.4629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7621    0.9071    1.3676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5079    1.6194   -1.5286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4667    0.2656   -1.8126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9346   -0.6115   -1.9148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4116   -1.5996    0.4116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6002   -1.9594   -0.8973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0252   -1.4584    2.4899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6201    3.1961   -0.7613 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4904   -1.8125    2.3999 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8744   -1.4582    2.8691 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0478   -0.7458    2.1535 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 19 25  1  0
 25 26  2  0
 25 27  1  0
 15 28  1  0
  8 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32  2  1  0
 31  6  1  0
 28 12  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  7 36  1  0
  9 37  1  0
  9 38  1  0
 11 39  1  0
 11 40  1  0
 11 41  1  0
 13 42  1  0
 14 43  1  0
 18 44  1  0
 19 45  1  6
 20 46  1  0
 20 47  1  0
 21 48  1  0
 21 49  1  0
 24 50  1  0
 27 51  1  0
 29 52  1  0
 30 53  1  0
 32 54  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
ZD1694	Kegg
Tomudex	Kegg
ZD-1694	HMDB
ICI-D1694	HMDB
N-(5-(N-(3,4-Dihydro-2-methyl-4-oxoquinazolin-6-ylmethyl)-N-methylamino)-2-thenoyl)-L-glutamic acid	HMDB
Arkomédika brand OF raltitrexed	HMDB
AstraZeneca brand OF raltitrexed	HMDB
ICI D1694	HMDB
Zeneca brand OF raltitrexed	HMDB
Raltitrexed	KEGG

Chemical Formula

C₂₁H₂₂N₄O₆S

Average Molecular Weight

458.488

Monoisotopic Molecular Weight

458.126005146

IUPAC Name

(2S)-2-[(5-{methyl[(2-methyl-4-oxo-1,4-dihydroquinazolin-6-yl)methyl]amino}thiophen-2-yl)formamido]pentanedioic acid

Traditional Name

raltitrexed

CAS Registry Number

112887-68-0

SMILES

CN(CC1=CC2=C(NC(C)=NC2=O)C=C1)C1=CC=C(S1)C(=O)N[C@@H](CCC(O)=O)C(O)=O

InChI Identifier

InChI=1S/C21H22N4O6S/c1-11-22-14-4-3-12(9-13(14)19(28)23-11)10-25(2)17-7-6-16(32-17)20(29)24-15(21(30)31)5-8-18(26)27/h3-4,6-7,9,15H,5,8,10H2,1-2H3,(H,24,29)(H,26,27)(H,30,31)(H,22,23,28)/t15-/m0/s1

InChI Key

IVTVGDXNLFLDRM-HNNXBMFYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Glutamic acid and derivatives

Alternative Parents

Substituents

Glutamic acid or derivatives
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Diazanaphthalene
Quinazoline
2-heteroaryl carboxamide
Thiophene carboxamide
Thiophene carboxylic acid or derivatives
Dialkylarylamine
Hydroxypyrimidine
2,5-disubstituted thiophene
Pyrimidine
Dicarboxylic acid or derivatives
2-aminothiophene
Benzenoid
Heteroaromatic compound
Thiophene
Carboxamide group
Secondary carboxylic acid amide
Azacycle
Carboxylic acid
Organoheterocyclic compound
Carbonyl group
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

N-acyl-amino acid (CHEBI:5847 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	180 - 184 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.018 g/L	Not Available
LogP	-1.2	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.018 g/L	ALOGPS
logP	1.65	ALOGPS
logP	1.97	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	3.72	ChemAxon
pKa (Strongest Basic)	-0.46	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	148.4 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	117.39 m³·mol⁻¹	ChemAxon
Polarizability	45.55 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]+	202.539	31661259
DarkChem	[M-H]-	193.888	31661259
DeepCCS	[M+H]+	200.157	30932474
DeepCCS	[M-H]-	197.762	30932474
DeepCCS	[M-2H]-	230.645	30932474
DeepCCS	[M+Na]+	206.07	30932474
AllCCS	[M+H]+	203.2	32859911
AllCCS	[M+H-H2O]+	201.3	32859911
AllCCS	[M+NH4]+	204.9	32859911
AllCCS	[M+Na]+	205.4	32859911
AllCCS	[M-H]-	198.2	32859911
AllCCS	[M+Na-2H]-	198.8	32859911
AllCCS	[M+HCOO]-	199.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Raltitrexed	CN(CC1=CC2=C(NC(C)=NC2=O)C=C1)C1=CC=C(S1)C(=O)N[C@@H](CCC(O)=O)C(O)=O	4769.2	Standard polar	33892256
Raltitrexed	CN(CC1=CC2=C(NC(C)=NC2=O)C=C1)C1=CC=C(S1)C(=O)N[C@@H](CCC(O)=O)C(O)=O	2849.0	Standard non polar	33892256
Raltitrexed	CN(CC1=CC2=C(NC(C)=NC2=O)C=C1)C1=CC=C(S1)C(=O)N[C@@H](CCC(O)=O)C(O)=O	4544.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Raltitrexed,1TMS,isomer #1	CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N[C@@H](CCC(=O)O[Si](C)(C)C)C(=O)O)S3)=CC=C2[NH]1	4297.5	Semi standard non polar	33892256
Raltitrexed,1TMS,isomer #2	CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N[C@@H](CCC(=O)O)C(=O)O[Si](C)(C)C)S3)=CC=C2[NH]1	4277.8	Semi standard non polar	33892256
Raltitrexed,1TMS,isomer #3	CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N[C@@H](CCC(=O)O)C(=O)O)S3)=CC=C2N1[Si](C)(C)C	4377.9	Semi standard non polar	33892256
Raltitrexed,1TMS,isomer #4	CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N([C@@H](CCC(=O)O)C(=O)O)[Si](C)(C)C)S3)=CC=C2[NH]1	4237.1	Semi standard non polar	33892256
Raltitrexed,2TMS,isomer #1	CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N[C@@H](CCC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C)S3)=CC=C2[NH]1	4183.7	Semi standard non polar	33892256
Raltitrexed,2TMS,isomer #2	CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N([C@@H](CCC(=O)O[Si](C)(C)C)C(=O)O)[Si](C)(C)C)S3)=CC=C2[NH]1	4101.8	Semi standard non polar	33892256
Raltitrexed,2TMS,isomer #3	CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N[C@@H](CCC(=O)O[Si](C)(C)C)C(=O)O)S3)=CC=C2N1[Si](C)(C)C	4266.9	Semi standard non polar	33892256
Raltitrexed,2TMS,isomer #4	CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N([C@@H](CCC(=O)O)C(=O)O[Si](C)(C)C)[Si](C)(C)C)S3)=CC=C2[NH]1	4141.2	Semi standard non polar	33892256
Raltitrexed,2TMS,isomer #5	CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N[C@@H](CCC(=O)O)C(=O)O[Si](C)(C)C)S3)=CC=C2N1[Si](C)(C)C	4244.1	Semi standard non polar	33892256
Raltitrexed,2TMS,isomer #6	CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N([C@@H](CCC(=O)O)C(=O)O)[Si](C)(C)C)S3)=CC=C2N1[Si](C)(C)C	4182.8	Semi standard non polar	33892256
Raltitrexed,3TMS,isomer #1	CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N([C@@H](CCC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C)S3)=CC=C2[NH]1	4036.7	Semi standard non polar	33892256
Raltitrexed,3TMS,isomer #1	CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N([C@@H](CCC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C)S3)=CC=C2[NH]1	3834.0	Standard non polar	33892256
Raltitrexed,3TMS,isomer #1	CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N([C@@H](CCC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C)S3)=CC=C2[NH]1	4891.3	Standard polar	33892256
Raltitrexed,3TMS,isomer #2	CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N[C@@H](CCC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C)S3)=CC=C2N1[Si](C)(C)C	4125.6	Semi standard non polar	33892256
Raltitrexed,3TMS,isomer #2	CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N[C@@H](CCC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C)S3)=CC=C2N1[Si](C)(C)C	3837.1	Standard non polar	33892256
Raltitrexed,3TMS,isomer #2	CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N[C@@H](CCC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C)S3)=CC=C2N1[Si](C)(C)C	4862.7	Standard polar	33892256
Raltitrexed,3TMS,isomer #3	CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N([C@@H](CCC(=O)O[Si](C)(C)C)C(=O)O)[Si](C)(C)C)S3)=CC=C2N1[Si](C)(C)C	4063.7	Semi standard non polar	33892256
Raltitrexed,3TMS,isomer #3	CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N([C@@H](CCC(=O)O[Si](C)(C)C)C(=O)O)[Si](C)(C)C)S3)=CC=C2N1[Si](C)(C)C	3884.1	Standard non polar	33892256
Raltitrexed,3TMS,isomer #3	CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N([C@@H](CCC(=O)O[Si](C)(C)C)C(=O)O)[Si](C)(C)C)S3)=CC=C2N1[Si](C)(C)C	4944.3	Standard polar	33892256
Raltitrexed,3TMS,isomer #4	CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N([C@@H](CCC(=O)O)C(=O)O[Si](C)(C)C)[Si](C)(C)C)S3)=CC=C2N1[Si](C)(C)C	4095.5	Semi standard non polar	33892256
Raltitrexed,3TMS,isomer #4	CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N([C@@H](CCC(=O)O)C(=O)O[Si](C)(C)C)[Si](C)(C)C)S3)=CC=C2N1[Si](C)(C)C	3850.5	Standard non polar	33892256
Raltitrexed,3TMS,isomer #4	CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N([C@@H](CCC(=O)O)C(=O)O[Si](C)(C)C)[Si](C)(C)C)S3)=CC=C2N1[Si](C)(C)C	4901.7	Standard polar	33892256
Raltitrexed,4TMS,isomer #1	CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N([C@@H](CCC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C)S3)=CC=C2N1[Si](C)(C)C	3997.4	Semi standard non polar	33892256
Raltitrexed,4TMS,isomer #1	CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N([C@@H](CCC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C)S3)=CC=C2N1[Si](C)(C)C	3759.8	Standard non polar	33892256
Raltitrexed,4TMS,isomer #1	CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N([C@@H](CCC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C)S3)=CC=C2N1[Si](C)(C)C	4507.8	Standard polar	33892256
Raltitrexed,1TBDMS,isomer #1	CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N[C@@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O)S3)=CC=C2[NH]1	4576.1	Semi standard non polar	33892256
Raltitrexed,1TBDMS,isomer #2	CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N[C@@H](CCC(=O)O)C(=O)O[Si](C)(C)C(C)(C)C)S3)=CC=C2[NH]1	4551.4	Semi standard non polar	33892256
Raltitrexed,1TBDMS,isomer #3	CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N[C@@H](CCC(=O)O)C(=O)O)S3)=CC=C2N1[Si](C)(C)C(C)(C)C	4568.6	Semi standard non polar	33892256
Raltitrexed,1TBDMS,isomer #4	CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N([C@@H](CCC(=O)O)C(=O)O)[Si](C)(C)C(C)(C)C)S3)=CC=C2[NH]1	4500.8	Semi standard non polar	33892256
Raltitrexed,2TBDMS,isomer #1	CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N[C@@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)S3)=CC=C2[NH]1	4641.1	Semi standard non polar	33892256
Raltitrexed,2TBDMS,isomer #2	CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N([C@@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C)S3)=CC=C2[NH]1	4584.6	Semi standard non polar	33892256
Raltitrexed,2TBDMS,isomer #3	CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N[C@@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O)S3)=CC=C2N1[Si](C)(C)C(C)(C)C	4667.4	Semi standard non polar	33892256
Raltitrexed,2TBDMS,isomer #4	CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N([C@@H](CCC(=O)O)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)S3)=CC=C2[NH]1	4589.9	Semi standard non polar	33892256
Raltitrexed,2TBDMS,isomer #5	CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N[C@@H](CCC(=O)O)C(=O)O[Si](C)(C)C(C)(C)C)S3)=CC=C2N1[Si](C)(C)C(C)(C)C	4638.4	Semi standard non polar	33892256
Raltitrexed,2TBDMS,isomer #6	CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N([C@@H](CCC(=O)O)C(=O)O)[Si](C)(C)C(C)(C)C)S3)=CC=C2N1[Si](C)(C)C(C)(C)C	4601.4	Semi standard non polar	33892256
Raltitrexed,3TBDMS,isomer #1	CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N([C@@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)S3)=CC=C2[NH]1	4651.0	Semi standard non polar	33892256
Raltitrexed,3TBDMS,isomer #1	CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N([C@@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)S3)=CC=C2[NH]1	4308.0	Standard non polar	33892256
Raltitrexed,3TBDMS,isomer #1	CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N([C@@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)S3)=CC=C2[NH]1	4942.6	Standard polar	33892256
Raltitrexed,3TBDMS,isomer #2	CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N[C@@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)S3)=CC=C2N1[Si](C)(C)C(C)(C)C	4691.6	Semi standard non polar	33892256
Raltitrexed,3TBDMS,isomer #2	CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N[C@@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)S3)=CC=C2N1[Si](C)(C)C(C)(C)C	4297.4	Standard non polar	33892256
Raltitrexed,3TBDMS,isomer #2	CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N[C@@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)S3)=CC=C2N1[Si](C)(C)C(C)(C)C	4901.0	Standard polar	33892256
Raltitrexed,3TBDMS,isomer #3	CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N([C@@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C)S3)=CC=C2N1[Si](C)(C)C(C)(C)C	4652.4	Semi standard non polar	33892256
Raltitrexed,3TBDMS,isomer #3	CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N([C@@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C)S3)=CC=C2N1[Si](C)(C)C(C)(C)C	4306.6	Standard non polar	33892256
Raltitrexed,3TBDMS,isomer #3	CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N([C@@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C)S3)=CC=C2N1[Si](C)(C)C(C)(C)C	4947.5	Standard polar	33892256
Raltitrexed,3TBDMS,isomer #4	CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N([C@@H](CCC(=O)O)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)S3)=CC=C2N1[Si](C)(C)C(C)(C)C	4652.4	Semi standard non polar	33892256
Raltitrexed,3TBDMS,isomer #4	CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N([C@@H](CCC(=O)O)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)S3)=CC=C2N1[Si](C)(C)C(C)(C)C	4279.9	Standard non polar	33892256
Raltitrexed,3TBDMS,isomer #4	CC1=NC(=O)C2=CC(CN(C)C3=CC=C(C(=O)N([C@@H](CCC(=O)O)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)S3)=CC=C2N1[Si](C)(C)C(C)(C)C	4927.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Raltitrexed GC-MS (Non-derivatized) - 70eV, Positive	splash10-03dl-2443900000-4123f916ebf757efa490	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Raltitrexed GC-MS (2 TMS) - 70eV, Positive	splash10-00dr-7321290000-bce279f690f228594cb4	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Raltitrexed 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 - Raltitrexed , positive-QTOF	splash10-03k9-0709000000-b0a922c0009fee349863	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Raltitrexed 35V, Positive-QTOF	splash10-0229-0905000000-8495738b2ade19f86c55	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Raltitrexed 35V, Negative-QTOF	splash10-0a4i-0141900000-ff3efc6165c65f4a9024	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Raltitrexed 10V, Positive-QTOF	splash10-074l-0512900000-f514d4a6b300e1598c10	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Raltitrexed 20V, Positive-QTOF	splash10-0h90-0932200000-df9ed4d0d58576d2bb3f	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Raltitrexed 40V, Positive-QTOF	splash10-00di-0910000000-639daf8403905e6f1108	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Raltitrexed 10V, Negative-QTOF	splash10-001i-0290000000-b82035dbae7250dd815a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Raltitrexed 20V, Negative-QTOF	splash10-0bvj-0695700000-22b802197672293574e8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Raltitrexed 40V, Negative-QTOF	splash10-0r09-6940000000-c21b12820e7259aeaa79	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Raltitrexed 10V, Positive-QTOF	splash10-0a4i-0002900000-ab80ccf8854a5fa05e39	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Raltitrexed 20V, Positive-QTOF	splash10-03di-0309000000-662b7467b152c14db878	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Raltitrexed 40V, Positive-QTOF	splash10-03nc-0964000000-03c9a6de56b48b2a5430	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Raltitrexed 10V, Negative-QTOF	splash10-0671-0294800000-11e71794a8ea12903210	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Raltitrexed 20V, Negative-QTOF	splash10-004j-2839600000-da164ebd563c294893c2	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Raltitrexed 40V, Negative-QTOF	splash10-066r-1893200000-ac9baba8ea2c00c97300	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

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 DB00293	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00293	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00293

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

94568

KEGG Compound ID

C11372

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Raltitrexed

METLIN ID

Not Available

PubChem Compound

104758

PDB ID

D16

ChEBI ID

Not Available

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. Folylpolyglutamate synthase, mitochondrial

General function:: Involved in tetrahydrofolylpolyglutamate synthase activity
Specific function:: Catalyzes conversion of folates to polyglutamate derivatives allowing concentration of folate compounds in the cell and the intracellular retention of these cofactors, which are important substrates for most of the folate-dependent enzymes that are involved in one-carbon transfer reactions involved in purine, pyrimidine and amino acid synthesis. Unsubstitued reduced folates are the preferred substrates. Metabolizes methotrexate (MTX) to polyglutamates.
Gene Name:: FPGS
Uniprot ID:: Q05932
Molecular weight:: 59173.37

References

Innocenti F, Ratain MJ: Update on pharmacogenetics in cancer chemotherapy. Eur J Cancer. 2002 Mar;38(5):639-44. [PubMed:11916544 ]

Enzyme Details

2. 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

Yin MB, Guo B, Panadero A, Frank C, Wrzosek C, Slocum HK, Rustum YM: Cyclin E-cdk2 activation is associated with cell cycle arrest and inhibition of DNA replication induced by the thymidylate synthase inhibitor Tomudex. Exp Cell Res. 1999 Feb 25;247(1):189-99. [PubMed:10047461 ]
Cao S, McGuire JJ, Rustum YM: Antitumor activity of ZD1694 (tomudex) against human head and neck cancer in nude mouse models: role of dosing schedule and plasma thymidine. Clin Cancer Res. 1999 Jul;5(7):1925-34. [PubMed:10430100 ]
Ferguson PJ, Collins O, Dean NM, DeMoor J, Li CS, Vincent MD, Koropatnick J: Antisense down-regulation of thymidylate synthase to suppress growth and enhance cytotoxicity of 5-FUdR, 5-FU and Tomudex in HeLa cells. Br J Pharmacol. 1999 Aug;127(8):1777-86. [PubMed:10482907 ]
Orlandi L, Bearzatto A, Abolafio G, De Marco C, Daidone MG, Zaffaroni N: Involvement of bcl-2 and p21waf1 proteins in response of human breast cancer cell clones to Tomudex. Br J Cancer. 1999 Sep;81(2):252-60. [PubMed:10496350 ]
Grem JL, Sorensen JM, Cullen E, Takimoto CH, Steinberg SM, Chen AP, Hamilton JM, Arbuck SG, McAtee N, Lawrence D, Goldspiel B, Johnston PG, Allegra CJ: A Phase I study of raltitrexed, an antifolate thymidylate synthase inhibitor, in adult patients with advanced solid tumors. Clin Cancer Res. 1999 Sep;5(9):2381-91. [PubMed:10499608 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Yang Z, Waldman AS, Wyatt MD: DNA damage and homologous recombination signaling induced by thymidylate deprivation. Biochem Pharmacol. 2008 Oct 15;76(8):987-96. doi: 10.1016/j.bcp.2008.08.010. Epub 2008 Aug 19. [PubMed:18773878 ]
Chen VJ, Bewley JR, Andis SL, Schultz RM, Iversen PW, Shih C, Mendelsohn LG, Seitz DE, Tonkinson JL: Cellular pharmacology of MTA: a correlation of MTA-induced cellular toxicity and in vitro enzyme inhibition with its effect on intracellular folate and nucleoside triphosphate pools in CCRF-CEM cells. Semin Oncol. 1999 Apr;26(2 Suppl 6):48-54. [PubMed:10598555 ]
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 ]

Showing metabocard for Raltitrexed (HMDB0014438)

MOL for HMDB0014438 (Raltitrexed)

3D MOL for HMDB0014438 (Raltitrexed)

3D SDF for HMDB0014438 (Raltitrexed)

3D-SDF for HMDB0014438 (Raltitrexed)

PDB for HMDB0014438 (Raltitrexed)

3D PDB for HMDB0014438 (Raltitrexed)

SMILES for HMDB0014438 (Raltitrexed)

INCHI for HMDB0014438 (Raltitrexed)

Structure for HMDB0014438 (Raltitrexed)

3D Structure for HMDB0014438 (Raltitrexed)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References