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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:52:03 UTC

HMDB ID

HMDB0015603

Secondary Accession Numbers

HMDB15603

Metabolite Identification

Common Name

Ximelagatran

Description

Ximelagatran, also known as exanta or H 376-95, belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. There was also a numerically higher mortality against warfarin. Ximelagatran is a drug which is used for the treatment of acute deep vein thrombosis. Ximelagatran was expected to replace warfarin and sometimes aspirin and heparin in many therapeutic settings, including deep venous thrombosis, prevention of secondary venous thromboembolism and complications of atrial fibrillation such as stroke. Ximelagatran is a very strong basic compound (based on its pKa). In humans, ximelagatran is involved in ximelagatran action pathway. Subsequent analysis of Phase 2 clinical study data using extreme value modelling (see Extreme value theory) showed that the elevated liver enzyme levels observed in Phase 3 clinical studies could have been predicted; if this had been known at the time, it might have affected decisions on future development of the compound. The efficacy of ximelagatran for these indications had been well documented, except for non valvular atrial fibrillation. A disadvantage recognised early was the absence of an antidote in case acute bleeding develops, while warfarin can be antagonised by prothrombin complex concentrate and/or vitamin K and heparin by protamine sulfate. Ximelagatran, a direct thrombin inhibitor, was the first member of this class that can be taken orally. It is taken orally twice daily, and rapidly absorbed by the small intestine.

Structure

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


  Mrv0541 02231218002D          

 34 36  0  0  1  0            999 V2000
    6.6001   -2.5484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0051   -1.0370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8876   -4.6919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8876   -3.2629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2906    5.1506    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3626   -1.8339    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5376   -3.2629    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2906    0.2005    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7196    4.3256    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2906    4.3256    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7751   -3.9774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3626   -3.2629    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3626   -4.6919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6001   -3.9774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7751   -5.4063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0127   -4.6919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5761   -1.0370    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.6001   -5.4063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5657   -1.6204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7792   -0.8235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7751   -2.5484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2906   -0.6245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1251   -3.9774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3001   -3.9774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0051    0.6130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0051    1.4380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2906    1.8505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7196    1.8505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -4.6919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2906    2.6755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7196    2.6755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0051    3.0880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -5.4063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0051    3.9131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 21  2  0  0  0  0
  2 22  2  0  0  0  0
  3 24  1  0  0  0  0
  3 29  1  0  0  0  0
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 12  7  1  1  0  0  0
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  8 22  1  0  0  0  0
  8 25  1  0  0  0  0
  9 34  1  0  0  0  0
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 17 22  1  1  0  0  0
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 27 30  1  0  0  0  0
 28 31  2  0  0  0  0
 29 33  1  0  0  0  0
 30 32  2  0  0  0  0
 31 32  1  0  0  0  0
 32 34  1  0  0  0  0
M  END

HMDB0015603
     RDKit          3D
Ximelagatran
 69 71  0  0  0  0  0  0  0  0999 V2000
   -7.1880    3.9636    1.9758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8407    4.1061    1.2579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7164    2.9367    0.4734 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5772    2.7014   -0.3485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7419    3.6160   -0.2906 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5209    1.4591   -1.1367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3508    1.1469   -1.7189 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1755    0.6110   -1.3691 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4306    1.2987   -0.3045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9645    1.7235    0.7790 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0305    1.5559   -0.3931 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9465    2.1910    0.4296 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7039    2.5364   -0.8463 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9819    1.2904   -1.3593 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7448    0.0514   -1.2072 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6129   -0.1911   -2.1142 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6289   -0.9002   -0.1749 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4279   -2.1011   -0.1096 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8054   -1.7559    0.3385 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1894   -0.4770    0.6563 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4709   -0.1953    1.0624 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3907   -1.1989    1.1562 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7723   -0.9356    1.5882 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7263   -1.9804    1.6848 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1309    0.2559    1.8855 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4133    0.5650    2.2967 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0463   -2.5122    0.8439 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7588   -2.7739    0.4392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0986   -0.8580   -1.0044 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.6934   -1.1824    0.3193 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4340    1.4947    1.1140 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.7569    0.8241    1.3099 H   0  0  0  0  0  0  0  0  0  0  0  0
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    6.7573   -3.3327    0.9098 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4655   -3.8030    0.1874 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.9511   -1.6503    1.0333 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
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  8 29  1  0
 29 30  1  0
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 31 32  1  0
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 33 34  1  0
 14 11  1  0
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  1 35  1  0
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  1 37  1  0
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 31 63  1  0
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 33 66  1  0
 33 67  1  0
 34 68  1  0
 34 69  1  0
M  END


  Mrv0541 02231218002D          

 34 36  0  0  1  0            999 V2000
    6.6001   -2.5484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0051   -1.0370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8876   -4.6919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8876   -3.2629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2906    5.1506    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3626   -1.8339    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5376   -3.2629    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2906    0.2005    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7196    4.3256    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2906    4.3256    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7751   -3.9774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3626   -3.2629    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3626   -4.6919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6001   -3.9774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.0127   -4.6919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.6001   -5.4063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5657   -1.6204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.3001   -3.9774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0051    0.6130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0625   -4.6919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2906    2.6755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7196    2.6755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0051    3.0880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -5.4063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0051    3.9131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 21  2  0  0  0  0
  2 22  2  0  0  0  0
  3 24  1  0  0  0  0
  3 29  1  0  0  0  0
  4 24  2  0  0  0  0
  5 10  1  0  0  0  0
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  6 21  1  0  0  0  0
 12  7  1  1  0  0  0
  7 23  1  0  0  0  0
  8 22  1  0  0  0  0
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  9 34  1  0  0  0  0
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 15 18  1  0  0  0  0
 16 18  1  0  0  0  0
 17 20  1  0  0  0  0
 17 22  1  1  0  0  0
 19 20  1  0  0  0  0
 23 24  1  0  0  0  0
 25 26  1  0  0  0  0
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 28 31  2  0  0  0  0
 29 33  1  0  0  0  0
 30 32  2  0  0  0  0
 31 32  1  0  0  0  0
 32 34  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015603

> <DATABASE_NAME>
hmdb

> <SMILES>
CCOC(=O)CN[C@@H](C(=O)N1CC[C@H]1C(=O)NCC1=CC=C(C=C1)C(\N)=N\O)C1CCCCC1

> <INCHI_IDENTIFIER>
InChI=1S/C24H35N5O5/c1-2-34-20(30)15-26-21(17-6-4-3-5-7-17)24(32)29-13-12-19(29)23(31)27-14-16-8-10-18(11-9-16)22(25)28-33/h8-11,17,19,21,26,33H,2-7,12-15H2,1H3,(H2,25,28)(H,27,31)/t19-,21+/m0/s1

> <INCHI_KEY>
ZXIBCJHYVWYIKI-PZJWPPBQSA-N

> <FORMULA>
C24H35N5O5

> <MOLECULAR_WEIGHT>
473.5652

> <EXACT_MASS>
473.263819255

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
52.148328970556044

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
ethyl 2-{[(1R)-1-cyclohexyl-2-[(2S)-2-[({4-[(Z)-N'-hydroxycarbamimidoyl]phenyl}methyl)carbamoyl]azetidin-1-yl]-2-oxoethyl]amino}acetate

> <ALOGPS_LOGP>
1.35

> <JCHEM_LOGP>
0.8693069373333331

> <ALOGPS_LOGS>
-3.75

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.13038811042912

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.63863186879247

> <JCHEM_PKA_STRONGEST_BASIC>
5.47950494930864

> <JCHEM_POLAR_SURFACE_AREA>
146.35000000000002

> <JCHEM_REFRACTIVITY>
126.56619999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.45e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ximelagatran

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015603
     RDKit          3D
Ximelagatran
 69 71  0  0  0  0  0  0  0  0999 V2000
   -7.1880    3.9636    1.9758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8407    4.1061    1.2579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7164    2.9367    0.4734 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5772    2.7014   -0.3485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7419    3.6160   -0.2906 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5209    1.4591   -1.1367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3508    1.1469   -1.7189 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1755    0.6110   -1.3691 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4306    1.2987   -0.3045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9645    1.7235    0.7790 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0305    1.5559   -0.3931 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9465    2.1910    0.4296 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7039    2.5364   -0.8463 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9819    1.2904   -1.3593 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7448    0.0514   -1.2072 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6129   -0.1911   -2.1142 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6289   -0.9002   -0.1749 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4279   -2.1011   -0.1096 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8054   -1.7559    0.3385 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1894   -0.4770    0.6563 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4709   -0.1953    1.0624 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3907   -1.1989    1.1562 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7723   -0.9356    1.5882 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7263   -1.9804    1.6848 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1309    0.2559    1.8855 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4133    0.5650    2.2967 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0463   -2.5122    0.8439 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7588   -2.7739    0.4392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0986   -0.8580   -1.0044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5361   -1.7619   -2.1291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3712   -3.1887   -1.6244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3644   -3.4422   -0.5343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8002   -2.2162    0.1965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6934   -1.1824    0.3193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2038    4.4642    2.9423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9838    4.3311    1.2818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4256    2.8895    2.1631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8559    4.9977    0.6104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0731    4.1527    2.0478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0339    0.6903   -0.5051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3111    1.6236   -1.9506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3372    1.3805   -2.7698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4621    0.6560   -2.2655 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6320    3.1340    0.9259 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4340    1.4947    1.1140 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7887    2.4662   -0.7875 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2722    3.4282   -1.3085 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6983    1.4579   -2.4233 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9269   -0.7659    0.6118 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4865   -2.5996   -1.1152 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0176   -2.8112    0.6276 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4276    0.2969    0.5689 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7569    0.8241    1.3099 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3288   -2.2015    0.8734 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8051   -2.5076    2.5699 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9695    1.0957    1.6371 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7573   -3.3327    0.9098 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4655   -3.8030    0.1874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0081   -1.0464   -0.9237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8844   -1.5787   -2.9916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6001   -1.6544   -2.3934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3508   -3.2782   -1.1707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4657   -3.9318   -2.4495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9839   -4.1715    0.2233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2863   -3.9071   -0.9847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6864   -1.7114   -0.2715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1159   -2.4532    1.2327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0978   -0.3167    0.8736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9511   -1.6503    1.0333 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 23 25  2  0
 25 26  1  0
 22 27  1  0
 27 28  2  0
  8 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 14 11  1  0
 28 19  1  0
 34 29  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  2 38  1  0
  2 39  1  0
  6 40  1  0
  6 41  1  0
  7 42  1  0
  8 43  1  6
 12 44  1  0
 12 45  1  0
 13 46  1  0
 13 47  1  0
 14 48  1  6
 17 49  1  0
 18 50  1  0
 18 51  1  0
 20 52  1  0
 21 53  1  0
 24 54  1  0
 24 55  1  0
 26 56  1  0
 27 57  1  0
 28 58  1  0
 29 59  1  0
 30 60  1  0
 30 61  1  0
 31 62  1  0
 31 63  1  0
 32 64  1  0
 32 65  1  0
 33 66  1  0
 33 67  1  0
 34 68  1  0
 34 69  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      12.320  -4.757   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      13.076  -1.936   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       5.390  -8.758   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       5.390  -6.091   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      11.742   9.614   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0      10.010  -3.423   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       8.470  -6.091   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0      11.742   0.374   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0      14.410   8.074   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0      11.742   8.074   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      10.780  -7.424   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.010  -6.091   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.010  -8.758   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.320  -7.424   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.780 -10.092   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.090  -8.758   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.409  -1.936   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.320 -10.092   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.523  -3.025   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.921  -1.537   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.780  -4.757   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.742  -1.166   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.700  -7.424   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.160  -7.424   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      13.076   1.144   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      13.076   2.684   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.742   3.454   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      14.410   3.454   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.850  -8.758   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      11.742   4.994   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      14.410   4.994   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      13.076   5.764   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.080 -10.092   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      13.076   7.304   0.000  0.00  0.00           C+0
CONECT    1   21                                                            
CONECT    2   22                                                            
CONECT    3   24   29                                                       
CONECT    4   24                                                            
CONECT    5   10                                                            
CONECT    6   17   19   21                                                  
CONECT    7   12   23                                                       
CONECT    8   22   25                                                       
CONECT    9   34                                                            
CONECT   10    5   34                                                       
CONECT   11   12   13   14                                                  
CONECT   12    7   11   21                                                  
CONECT   13   11   15                                                       
CONECT   14   11   16                                                       
CONECT   15   13   18                                                       
CONECT   16   14   18                                                       
CONECT   17    6   20   22                                                  
CONECT   18   15   16                                                       
CONECT   19    6   20                                                       
CONECT   20   17   19                                                       
CONECT   21    1    6   12                                                  
CONECT   22    2    8   17                                                  
CONECT   23    7   24                                                       
CONECT   24    3    4   23                                                  
CONECT   25    8   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26   30                                                       
CONECT   28   26   31                                                       
CONECT   29    3   33                                                       
CONECT   30   27   32                                                       
CONECT   31   28   32                                                       
CONECT   32   30   31   34                                                  
CONECT   33   29                                                            
CONECT   34    9   10   32                                                  
MASTER        0    0    0    0    0    0    0    0   34    0   72    0
END

COMPND    HMDB0015603
HETATM    1  C1  UNL     1      -7.188   3.964   1.976  1.00  0.00           C  
HETATM    2  C2  UNL     1      -5.841   4.106   1.258  1.00  0.00           C  
HETATM    3  O1  UNL     1      -5.716   2.937   0.473  1.00  0.00           O  
HETATM    4  C3  UNL     1      -4.577   2.701  -0.348  1.00  0.00           C  
HETATM    5  O2  UNL     1      -3.742   3.616  -0.291  1.00  0.00           O  
HETATM    6  C4  UNL     1      -4.521   1.459  -1.137  1.00  0.00           C  
HETATM    7  N1  UNL     1      -3.351   1.147  -1.719  1.00  0.00           N  
HETATM    8  C5  UNL     1      -2.176   0.611  -1.369  1.00  0.00           C  
HETATM    9  C6  UNL     1      -1.431   1.299  -0.305  1.00  0.00           C  
HETATM   10  O3  UNL     1      -1.964   1.723   0.779  1.00  0.00           O  
HETATM   11  N2  UNL     1      -0.030   1.556  -0.393  1.00  0.00           N  
HETATM   12  C7  UNL     1       0.946   2.191   0.430  1.00  0.00           C  
HETATM   13  C8  UNL     1       1.704   2.536  -0.846  1.00  0.00           C  
HETATM   14  C9  UNL     1       0.982   1.290  -1.359  1.00  0.00           C  
HETATM   15  C10 UNL     1       1.745   0.051  -1.207  1.00  0.00           C  
HETATM   16  O4  UNL     1       2.613  -0.191  -2.114  1.00  0.00           O  
HETATM   17  N3  UNL     1       1.629  -0.900  -0.175  1.00  0.00           N  
HETATM   18  C11 UNL     1       2.428  -2.101  -0.110  1.00  0.00           C  
HETATM   19  C12 UNL     1       3.805  -1.756   0.338  1.00  0.00           C  
HETATM   20  C13 UNL     1       4.189  -0.477   0.656  1.00  0.00           C  
HETATM   21  C14 UNL     1       5.471  -0.195   1.062  1.00  0.00           C  
HETATM   22  C15 UNL     1       6.391  -1.199   1.156  1.00  0.00           C  
HETATM   23  C16 UNL     1       7.772  -0.936   1.588  1.00  0.00           C  
HETATM   24  N4  UNL     1       8.726  -1.980   1.685  1.00  0.00           N  
HETATM   25  N5  UNL     1       8.131   0.256   1.885  1.00  0.00           N  
HETATM   26  O5  UNL     1       9.413   0.565   2.297  1.00  0.00           O  
HETATM   27  C17 UNL     1       6.046  -2.512   0.844  1.00  0.00           C  
HETATM   28  C18 UNL     1       4.759  -2.774   0.439  1.00  0.00           C  
HETATM   29  C19 UNL     1      -2.099  -0.858  -1.004  1.00  0.00           C  
HETATM   30  C20 UNL     1      -2.536  -1.762  -2.129  1.00  0.00           C  
HETATM   31  C21 UNL     1      -2.371  -3.189  -1.624  1.00  0.00           C  
HETATM   32  C22 UNL     1      -3.364  -3.442  -0.534  1.00  0.00           C  
HETATM   33  C23 UNL     1      -3.800  -2.216   0.196  1.00  0.00           C  
HETATM   34  C24 UNL     1      -2.693  -1.182   0.319  1.00  0.00           C  
HETATM   35  H1  UNL     1      -7.204   4.464   2.942  1.00  0.00           H  
HETATM   36  H2  UNL     1      -7.984   4.331   1.282  1.00  0.00           H  
HETATM   37  H3  UNL     1      -7.426   2.889   2.163  1.00  0.00           H  
HETATM   38  H4  UNL     1      -5.856   4.998   0.610  1.00  0.00           H  
HETATM   39  H5  UNL     1      -5.073   4.153   2.048  1.00  0.00           H  
HETATM   40  H6  UNL     1      -5.034   0.690  -0.505  1.00  0.00           H  
HETATM   41  H7  UNL     1      -5.311   1.624  -1.951  1.00  0.00           H  
HETATM   42  H8  UNL     1      -3.337   1.380  -2.770  1.00  0.00           H  
HETATM   43  H9  UNL     1      -1.462   0.656  -2.265  1.00  0.00           H  
HETATM   44  H10 UNL     1       0.632   3.134   0.926  1.00  0.00           H  
HETATM   45  H11 UNL     1       1.434   1.495   1.114  1.00  0.00           H  
HETATM   46  H12 UNL     1       2.789   2.466  -0.788  1.00  0.00           H  
HETATM   47  H13 UNL     1       1.272   3.428  -1.308  1.00  0.00           H  
HETATM   48  H14 UNL     1       0.698   1.458  -2.423  1.00  0.00           H  
HETATM   49  H15 UNL     1       0.927  -0.766   0.612  1.00  0.00           H  
HETATM   50  H16 UNL     1       2.487  -2.600  -1.115  1.00  0.00           H  
HETATM   51  H17 UNL     1       2.018  -2.811   0.628  1.00  0.00           H  
HETATM   52  H18 UNL     1       3.428   0.297   0.569  1.00  0.00           H  
HETATM   53  H19 UNL     1       5.757   0.824   1.310  1.00  0.00           H  
HETATM   54  H20 UNL     1       9.329  -2.201   0.873  1.00  0.00           H  
HETATM   55  H21 UNL     1       8.805  -2.508   2.570  1.00  0.00           H  
HETATM   56  H22 UNL     1       9.969   1.096   1.637  1.00  0.00           H  
HETATM   57  H23 UNL     1       6.757  -3.333   0.910  1.00  0.00           H  
HETATM   58  H24 UNL     1       4.466  -3.803   0.187  1.00  0.00           H  
HETATM   59  H25 UNL     1      -1.008  -1.046  -0.924  1.00  0.00           H  
HETATM   60  H26 UNL     1      -1.884  -1.579  -2.992  1.00  0.00           H  
HETATM   61  H27 UNL     1      -3.600  -1.654  -2.393  1.00  0.00           H  
HETATM   62  H28 UNL     1      -1.351  -3.278  -1.171  1.00  0.00           H  
HETATM   63  H29 UNL     1      -2.466  -3.932  -2.449  1.00  0.00           H  
HETATM   64  H30 UNL     1      -2.984  -4.172   0.223  1.00  0.00           H  
HETATM   65  H31 UNL     1      -4.286  -3.907  -0.985  1.00  0.00           H  
HETATM   66  H32 UNL     1      -4.686  -1.711  -0.272  1.00  0.00           H  
HETATM   67  H33 UNL     1      -4.116  -2.453   1.233  1.00  0.00           H  
HETATM   68  H34 UNL     1      -3.098  -0.317   0.874  1.00  0.00           H  
HETATM   69  H35 UNL     1      -1.951  -1.650   1.033  1.00  0.00           H  
CONECT    1    2   35   36   37
CONECT    2    3   38   39
CONECT    3    4
CONECT    4    5    5    6
CONECT    6    7   40   41
CONECT    7    8   42
CONECT    8    9   29   43
CONECT    9   10   10   11
CONECT   11   12   14
CONECT   12   13   44   45
CONECT   13   14   46   47
CONECT   14   15   48
CONECT   15   16   16   17
CONECT   17   18   49
CONECT   18   19   50   51
CONECT   19   20   20   28
CONECT   20   21   52
CONECT   21   22   22   53
CONECT   22   23   27
CONECT   23   24   25   25
CONECT   24   54   55
CONECT   25   26
CONECT   26   56
CONECT   27   28   28   57
CONECT   28   58
CONECT   29   30   34   59
CONECT   30   31   60   61
CONECT   31   32   62   63
CONECT   32   33   64   65
CONECT   33   34   66   67
CONECT   34   68   69
END

HMDB0015603
     RDKit          3D
Ximelagatran
 69 71  0  0  0  0  0  0  0  0999 V2000
   -7.1880    3.9636    1.9758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8407    4.1061    1.2579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7164    2.9367    0.4734 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5772    2.7014   -0.3485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7419    3.6160   -0.2906 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5209    1.4591   -1.1367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3508    1.1469   -1.7189 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1755    0.6110   -1.3691 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4306    1.2987   -0.3045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9645    1.7235    0.7790 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0305    1.5559   -0.3931 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9465    2.1910    0.4296 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7039    2.5364   -0.8463 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9819    1.2904   -1.3593 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7448    0.0514   -1.2072 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6129   -0.1911   -2.1142 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6289   -0.9002   -0.1749 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4279   -2.1011   -0.1096 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8054   -1.7559    0.3385 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1894   -0.4770    0.6563 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4709   -0.1953    1.0624 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3907   -1.1989    1.1562 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7723   -0.9356    1.5882 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7263   -1.9804    1.6848 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1309    0.2559    1.8855 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4133    0.5650    2.2967 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0463   -2.5122    0.8439 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7588   -2.7739    0.4392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0986   -0.8580   -1.0044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5361   -1.7619   -2.1291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3712   -3.1887   -1.6244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3644   -3.4422   -0.5343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8002   -2.2162    0.1965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6934   -1.1824    0.3193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2038    4.4642    2.9423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9838    4.3311    1.2818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4256    2.8895    2.1631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8559    4.9977    0.6104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0731    4.1527    2.0478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0339    0.6903   -0.5051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3111    1.6236   -1.9506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3372    1.3805   -2.7698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4621    0.6560   -2.2655 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6320    3.1340    0.9259 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4340    1.4947    1.1140 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7887    2.4662   -0.7875 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2722    3.4282   -1.3085 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6983    1.4579   -2.4233 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9269   -0.7659    0.6118 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4865   -2.5996   -1.1152 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0176   -2.8112    0.6276 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4276    0.2969    0.5689 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7569    0.8241    1.3099 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3288   -2.2015    0.8734 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8051   -2.5076    2.5699 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9695    1.0957    1.6371 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7573   -3.3327    0.9098 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4655   -3.8030    0.1874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0081   -1.0464   -0.9237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8844   -1.5787   -2.9916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6001   -1.6544   -2.3934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3508   -3.2782   -1.1707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4657   -3.9318   -2.4495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9839   -4.1715    0.2233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2863   -3.9071   -0.9847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6864   -1.7114   -0.2715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1159   -2.4532    1.2327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0978   -0.3167    0.8736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9511   -1.6503    1.0333 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 23 25  2  0
 25 26  1  0
 22 27  1  0
 27 28  2  0
  8 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 14 11  1  0
 28 19  1  0
 34 29  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  2 38  1  0
  2 39  1  0
  6 40  1  0
  6 41  1  0
  7 42  1  0
  8 43  1  6
 12 44  1  0
 12 45  1  0
 13 46  1  0
 13 47  1  0
 14 48  1  6
 17 49  1  0
 18 50  1  0
 18 51  1  0
 20 52  1  0
 21 53  1  0
 24 54  1  0
 24 55  1  0
 26 56  1  0
 27 57  1  0
 28 58  1  0
 29 59  1  0
 30 60  1  0
 30 61  1  0
 31 62  1  0
 31 63  1  0
 32 64  1  0
 32 65  1  0
 33 66  1  0
 33 67  1  0
 34 68  1  0
 34 69  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Ethyl 2-[[(1R)-1-cyclohexyl-2- [(2S)-2-[[4-(n'-hydroxycarbamimidoyl) phenyl]methylcarbamoyl]azetidin-1-yl]- 2-oxo-ethyl]amino]acetate	ChEBI
Exanta	ChEBI
Exarta	ChEBI
H 376-95	ChEBI
H 376/95	ChEBI
H 37695	ChEBI
Ximelagatran (oxime form)	ChEBI
Ximelagatranum	ChEBI
Ethyl 2-[[(1R)-1-cyclohexyl-2- [(2S)-2-[[4-(n'-hydroxycarbamimidoyl) phenyl]methylcarbamoyl]azetidin-1-yl]- 2-oxo-ethyl]amino]acetic acid	Generator
XI-melagatran	HMDB
Glycine, N-((1R)1-cyclohexyl-2-((2S)-((((4-(amino(hydroxyimino)methyl)phenyl)methyl)amino)carbonyl)-1-azetidinyl)2-oxoethyl)-ethyl ester	HMDB
Glycine, N-((1)1-cyclohexyl-2-((2)-((((4-(amino(hydroxyimino)methyl)phenyl)methyl)amino)carbonyl)-1-azetidinyl)2-oxoethyl)-ethyl ester	HMDB

Chemical Formula

C₂₄H₃₅N₅O₅

Average Molecular Weight

473.5652

Monoisotopic Molecular Weight

473.263819255

IUPAC Name

ethyl 2-{[(1R)-1-cyclohexyl-2-[(2S)-2-[({4-[(Z)-N'-hydroxycarbamimidoyl]phenyl}methyl)carbamoyl]azetidin-1-yl]-2-oxoethyl]amino}acetate

Traditional Name

ximelagatran

CAS Registry Number

192939-46-1

SMILES

CCOC(=O)CN[C@@H](C(=O)N1CC[C@H]1C(=O)NCC1=CC=C(C=C1)C(\N)=N\O)C1CCCCC1

InChI Identifier

InChI=1S/C24H35N5O5/c1-2-34-20(30)15-26-21(17-6-4-3-5-7-17)24(32)29-13-12-19(29)23(31)27-14-16-8-10-18(11-9-16)22(25)28-33/h8-11,17,19,21,26,33H,2-7,12-15H2,1H3,(H2,25,28)(H,27,31)/t19-,21+/m0/s1

InChI Key

ZXIBCJHYVWYIKI-PZJWPPBQSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Dipeptides

Alternative Parents

Substituents

Alpha-dipeptide
Alpha-amino acid ester
Alpha-amino acid amide
Alpha-amino acid or derivatives
Monocyclic benzene moiety
Benzenoid
Amidoxime
Tertiary carboxylic acid amide
Amino acid or derivatives
Azetidine
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid ester
Amidine
Azacycle
Organoheterocyclic compound
Secondary amine
Secondary aliphatic amine
Monocarboxylic acid or derivatives
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
Organopnictogen compound
Organic nitrogen compound
Amine
Organic oxide
Organonitrogen compound
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

ethyl ester (CHEBI:65172 )
secondary amino compound (CHEBI:65172 )
carboxamide (CHEBI:65172 )
azetidines (CHEBI:65172 )
amidoxime (CHEBI:65172 )

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

Extracellular (HMDB: HMDB0015603)
Membrane (HMDB: HMDB0015603)

Source

Exogenous

Exogenous (HMDB: HMDB0015603)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Ximelagatran Action Pathway (PathBank: SMP0000279)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.084 g/L	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.084 g/L	ALOGPS
logP	1.35	ALOGPS
logP	0.87	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	9.64	ChemAxon
pKa (Strongest Basic)	5.48	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	146.35 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	126.57 m³·mol⁻¹	ChemAxon
Polarizability	52.15 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]+	210.175	31661259
DarkChem	[M-H]-	206.499	31661259
DeepCCS	[M+H]+	217.017	30932474
DeepCCS	[M-H]-	214.622	30932474
DeepCCS	[M-2H]-	247.683	30932474
DeepCCS	[M+Na]+	222.93	30932474
AllCCS	[M+H]+	210.6	32859911
AllCCS	[M+H-H2O]+	209.0	32859911
AllCCS	[M+NH4]+	212.2	32859911
AllCCS	[M+Na]+	212.6	32859911
AllCCS	[M-H]-	202.7	32859911
AllCCS	[M+Na-2H]-	204.1	32859911
AllCCS	[M+HCOO]-	205.8	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.	1.68 minutes	32390414
Predicted by Siyang on May 30, 2022	10.5383 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.93 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	233.4 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1316.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	167.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	162.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	165.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	97.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	317.0 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	354.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	961.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	805.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	351.4 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	970.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	215.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	279.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	317.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	490.2 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	133.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Ximelagatran	CCOC(=O)CN[C@@H](C(=O)N1CC[C@H]1C(=O)NCC1=CC=C(C=C1)C(\N)=N\O)C1CCCCC1	3902.3	Standard polar	33892256
Ximelagatran	CCOC(=O)CN[C@@H](C(=O)N1CC[C@H]1C(=O)NCC1=CC=C(C=C1)C(\N)=N\O)C1CCCCC1	3718.1	Standard non polar	33892256
Ximelagatran	CCOC(=O)CN[C@@H](C(=O)N1CC[C@H]1C(=O)NCC1=CC=C(C=C1)C(\N)=N\O)C1CCCCC1	4162.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Ximelagatran,1TMS,isomer #1	CCOC(=O)CN[C@@H](C(=O)N1CC[C@H]1C(=O)NCC1=CC=C(/C(=N/O)N[Si](C)(C)C)C=C1)C1CCCCC1	4145.6	Semi standard non polar	33892256
Ximelagatran,1TMS,isomer #1	CCOC(=O)CN[C@@H](C(=O)N1CC[C@H]1C(=O)NCC1=CC=C(/C(=N/O)N[Si](C)(C)C)C=C1)C1CCCCC1	3708.9	Standard non polar	33892256
Ximelagatran,1TMS,isomer #1	CCOC(=O)CN[C@@H](C(=O)N1CC[C@H]1C(=O)NCC1=CC=C(/C(=N/O)N[Si](C)(C)C)C=C1)C1CCCCC1	6234.4	Standard polar	33892256
Ximelagatran,1TMS,isomer #2	CCOC(=O)CN([C@@H](C(=O)N1CC[C@H]1C(=O)NCC1=CC=C(/C(N)=N/O)C=C1)C1CCCCC1)[Si](C)(C)C	4030.1	Semi standard non polar	33892256
Ximelagatran,1TMS,isomer #2	CCOC(=O)CN([C@@H](C(=O)N1CC[C@H]1C(=O)NCC1=CC=C(/C(N)=N/O)C=C1)C1CCCCC1)[Si](C)(C)C	3567.9	Standard non polar	33892256
Ximelagatran,1TMS,isomer #2	CCOC(=O)CN([C@@H](C(=O)N1CC[C@H]1C(=O)NCC1=CC=C(/C(N)=N/O)C=C1)C1CCCCC1)[Si](C)(C)C	6625.6	Standard polar	33892256
Ximelagatran,1TMS,isomer #3	CCOC(=O)CN[C@@H](C(=O)N1CC[C@H]1C(=O)N(CC1=CC=C(/C(N)=N/O)C=C1)[Si](C)(C)C)C1CCCCC1	3971.1	Semi standard non polar	33892256
Ximelagatran,1TMS,isomer #3	CCOC(=O)CN[C@@H](C(=O)N1CC[C@H]1C(=O)N(CC1=CC=C(/C(N)=N/O)C=C1)[Si](C)(C)C)C1CCCCC1	3587.0	Standard non polar	33892256
Ximelagatran,1TMS,isomer #3	CCOC(=O)CN[C@@H](C(=O)N1CC[C@H]1C(=O)N(CC1=CC=C(/C(N)=N/O)C=C1)[Si](C)(C)C)C1CCCCC1	6521.3	Standard polar	33892256
Ximelagatran,2TMS,isomer #1	CCOC(=O)CN([C@@H](C(=O)N1CC[C@H]1C(=O)NCC1=CC=C(/C(=N/O)N[Si](C)(C)C)C=C1)C1CCCCC1)[Si](C)(C)C	4043.1	Semi standard non polar	33892256
Ximelagatran,2TMS,isomer #1	CCOC(=O)CN([C@@H](C(=O)N1CC[C@H]1C(=O)NCC1=CC=C(/C(=N/O)N[Si](C)(C)C)C=C1)C1CCCCC1)[Si](C)(C)C	3632.1	Standard non polar	33892256
Ximelagatran,2TMS,isomer #1	CCOC(=O)CN([C@@H](C(=O)N1CC[C@H]1C(=O)NCC1=CC=C(/C(=N/O)N[Si](C)(C)C)C=C1)C1CCCCC1)[Si](C)(C)C	5875.9	Standard polar	33892256
Ximelagatran,2TMS,isomer #2	CCOC(=O)CN[C@@H](C(=O)N1CC[C@H]1C(=O)N(CC1=CC=C(/C(=N/O)N[Si](C)(C)C)C=C1)[Si](C)(C)C)C1CCCCC1	4006.0	Semi standard non polar	33892256
Ximelagatran,2TMS,isomer #2	CCOC(=O)CN[C@@H](C(=O)N1CC[C@H]1C(=O)N(CC1=CC=C(/C(=N/O)N[Si](C)(C)C)C=C1)[Si](C)(C)C)C1CCCCC1	3673.9	Standard non polar	33892256
Ximelagatran,2TMS,isomer #2	CCOC(=O)CN[C@@H](C(=O)N1CC[C@H]1C(=O)N(CC1=CC=C(/C(=N/O)N[Si](C)(C)C)C=C1)[Si](C)(C)C)C1CCCCC1	5737.4	Standard polar	33892256
Ximelagatran,2TMS,isomer #3	CCOC(=O)CN[C@@H](C(=O)N1CC[C@H]1C(=O)NCC1=CC=C(/C(=N/O)N([Si](C)(C)C)[Si](C)(C)C)C=C1)C1CCCCC1	4072.8	Semi standard non polar	33892256
Ximelagatran,2TMS,isomer #3	CCOC(=O)CN[C@@H](C(=O)N1CC[C@H]1C(=O)NCC1=CC=C(/C(=N/O)N([Si](C)(C)C)[Si](C)(C)C)C=C1)C1CCCCC1	3777.5	Standard non polar	33892256
Ximelagatran,2TMS,isomer #3	CCOC(=O)CN[C@@H](C(=O)N1CC[C@H]1C(=O)NCC1=CC=C(/C(=N/O)N([Si](C)(C)C)[Si](C)(C)C)C=C1)C1CCCCC1	5736.6	Standard polar	33892256
Ximelagatran,2TMS,isomer #4	CCOC(=O)CN([C@@H](C(=O)N1CC[C@H]1C(=O)N(CC1=CC=C(/C(N)=N/O)C=C1)[Si](C)(C)C)C1CCCCC1)[Si](C)(C)C	3917.8	Semi standard non polar	33892256
Ximelagatran,2TMS,isomer #4	CCOC(=O)CN([C@@H](C(=O)N1CC[C@H]1C(=O)N(CC1=CC=C(/C(N)=N/O)C=C1)[Si](C)(C)C)C1CCCCC1)[Si](C)(C)C	3544.6	Standard non polar	33892256
Ximelagatran,2TMS,isomer #4	CCOC(=O)CN([C@@H](C(=O)N1CC[C@H]1C(=O)N(CC1=CC=C(/C(N)=N/O)C=C1)[Si](C)(C)C)C1CCCCC1)[Si](C)(C)C	6289.1	Standard polar	33892256
Ximelagatran,3TMS,isomer #1	CCOC(=O)CN([C@@H](C(=O)N1CC[C@H]1C(=O)N(CC1=CC=C(/C(=N/O)N[Si](C)(C)C)C=C1)[Si](C)(C)C)C1CCCCC1)[Si](C)(C)C	3958.9	Semi standard non polar	33892256
Ximelagatran,3TMS,isomer #1	CCOC(=O)CN([C@@H](C(=O)N1CC[C@H]1C(=O)N(CC1=CC=C(/C(=N/O)N[Si](C)(C)C)C=C1)[Si](C)(C)C)C1CCCCC1)[Si](C)(C)C	3627.3	Standard non polar	33892256
Ximelagatran,3TMS,isomer #1	CCOC(=O)CN([C@@H](C(=O)N1CC[C@H]1C(=O)N(CC1=CC=C(/C(=N/O)N[Si](C)(C)C)C=C1)[Si](C)(C)C)C1CCCCC1)[Si](C)(C)C	5356.6	Standard polar	33892256
Ximelagatran,3TMS,isomer #2	CCOC(=O)CN([C@@H](C(=O)N1CC[C@H]1C(=O)NCC1=CC=C(/C(=N/O)N([Si](C)(C)C)[Si](C)(C)C)C=C1)C1CCCCC1)[Si](C)(C)C	4006.9	Semi standard non polar	33892256
Ximelagatran,3TMS,isomer #2	CCOC(=O)CN([C@@H](C(=O)N1CC[C@H]1C(=O)NCC1=CC=C(/C(=N/O)N([Si](C)(C)C)[Si](C)(C)C)C=C1)C1CCCCC1)[Si](C)(C)C	3705.1	Standard non polar	33892256
Ximelagatran,3TMS,isomer #2	CCOC(=O)CN([C@@H](C(=O)N1CC[C@H]1C(=O)NCC1=CC=C(/C(=N/O)N([Si](C)(C)C)[Si](C)(C)C)C=C1)C1CCCCC1)[Si](C)(C)C	5361.4	Standard polar	33892256
Ximelagatran,3TMS,isomer #3	CCOC(=O)CN[C@@H](C(=O)N1CC[C@H]1C(=O)N(CC1=CC=C(/C(=N/O)N([Si](C)(C)C)[Si](C)(C)C)C=C1)[Si](C)(C)C)C1CCCCC1	3952.7	Semi standard non polar	33892256
Ximelagatran,3TMS,isomer #3	CCOC(=O)CN[C@@H](C(=O)N1CC[C@H]1C(=O)N(CC1=CC=C(/C(=N/O)N([Si](C)(C)C)[Si](C)(C)C)C=C1)[Si](C)(C)C)C1CCCCC1	3751.7	Standard non polar	33892256
Ximelagatran,3TMS,isomer #3	CCOC(=O)CN[C@@H](C(=O)N1CC[C@H]1C(=O)N(CC1=CC=C(/C(=N/O)N([Si](C)(C)C)[Si](C)(C)C)C=C1)[Si](C)(C)C)C1CCCCC1	5236.8	Standard polar	33892256
Ximelagatran,4TMS,isomer #1	CCOC(=O)CN([C@@H](C(=O)N1CC[C@H]1C(=O)N(CC1=CC=C(/C(=N/O)N([Si](C)(C)C)[Si](C)(C)C)C=C1)[Si](C)(C)C)C1CCCCC1)[Si](C)(C)C	3936.5	Semi standard non polar	33892256
Ximelagatran,4TMS,isomer #1	CCOC(=O)CN([C@@H](C(=O)N1CC[C@H]1C(=O)N(CC1=CC=C(/C(=N/O)N([Si](C)(C)C)[Si](C)(C)C)C=C1)[Si](C)(C)C)C1CCCCC1)[Si](C)(C)C	3694.9	Standard non polar	33892256
Ximelagatran,4TMS,isomer #1	CCOC(=O)CN([C@@H](C(=O)N1CC[C@H]1C(=O)N(CC1=CC=C(/C(=N/O)N([Si](C)(C)C)[Si](C)(C)C)C=C1)[Si](C)(C)C)C1CCCCC1)[Si](C)(C)C	4910.1	Standard polar	33892256
Ximelagatran,1TBDMS,isomer #1	CCOC(=O)CN[C@@H](C(=O)N1CC[C@H]1C(=O)NCC1=CC=C(/C(=N/O)N[Si](C)(C)C(C)(C)C)C=C1)C1CCCCC1	4343.6	Semi standard non polar	33892256
Ximelagatran,1TBDMS,isomer #1	CCOC(=O)CN[C@@H](C(=O)N1CC[C@H]1C(=O)NCC1=CC=C(/C(=N/O)N[Si](C)(C)C(C)(C)C)C=C1)C1CCCCC1	3879.4	Standard non polar	33892256
Ximelagatran,1TBDMS,isomer #1	CCOC(=O)CN[C@@H](C(=O)N1CC[C@H]1C(=O)NCC1=CC=C(/C(=N/O)N[Si](C)(C)C(C)(C)C)C=C1)C1CCCCC1	6112.3	Standard polar	33892256
Ximelagatran,1TBDMS,isomer #2	CCOC(=O)CN([C@@H](C(=O)N1CC[C@H]1C(=O)NCC1=CC=C(/C(N)=N/O)C=C1)C1CCCCC1)[Si](C)(C)C(C)(C)C	4288.7	Semi standard non polar	33892256
Ximelagatran,1TBDMS,isomer #2	CCOC(=O)CN([C@@H](C(=O)N1CC[C@H]1C(=O)NCC1=CC=C(/C(N)=N/O)C=C1)C1CCCCC1)[Si](C)(C)C(C)(C)C	3743.7	Standard non polar	33892256
Ximelagatran,1TBDMS,isomer #2	CCOC(=O)CN([C@@H](C(=O)N1CC[C@H]1C(=O)NCC1=CC=C(/C(N)=N/O)C=C1)C1CCCCC1)[Si](C)(C)C(C)(C)C	6578.7	Standard polar	33892256
Ximelagatran,1TBDMS,isomer #3	CCOC(=O)CN[C@@H](C(=O)N1CC[C@H]1C(=O)N(CC1=CC=C(/C(N)=N/O)C=C1)[Si](C)(C)C(C)(C)C)C1CCCCC1	4217.2	Semi standard non polar	33892256
Ximelagatran,1TBDMS,isomer #3	CCOC(=O)CN[C@@H](C(=O)N1CC[C@H]1C(=O)N(CC1=CC=C(/C(N)=N/O)C=C1)[Si](C)(C)C(C)(C)C)C1CCCCC1	3760.7	Standard non polar	33892256
Ximelagatran,1TBDMS,isomer #3	CCOC(=O)CN[C@@H](C(=O)N1CC[C@H]1C(=O)N(CC1=CC=C(/C(N)=N/O)C=C1)[Si](C)(C)C(C)(C)C)C1CCCCC1	6495.0	Standard polar	33892256
Ximelagatran,2TBDMS,isomer #1	CCOC(=O)CN([C@@H](C(=O)N1CC[C@H]1C(=O)NCC1=CC=C(/C(=N/O)N[Si](C)(C)C(C)(C)C)C=C1)C1CCCCC1)[Si](C)(C)C(C)(C)C	4481.2	Semi standard non polar	33892256
Ximelagatran,2TBDMS,isomer #1	CCOC(=O)CN([C@@H](C(=O)N1CC[C@H]1C(=O)NCC1=CC=C(/C(=N/O)N[Si](C)(C)C(C)(C)C)C=C1)C1CCCCC1)[Si](C)(C)C(C)(C)C	3969.5	Standard non polar	33892256
Ximelagatran,2TBDMS,isomer #1	CCOC(=O)CN([C@@H](C(=O)N1CC[C@H]1C(=O)NCC1=CC=C(/C(=N/O)N[Si](C)(C)C(C)(C)C)C=C1)C1CCCCC1)[Si](C)(C)C(C)(C)C	5739.3	Standard polar	33892256
Ximelagatran,2TBDMS,isomer #2	CCOC(=O)CN[C@@H](C(=O)N1CC[C@H]1C(=O)N(CC1=CC=C(/C(=N/O)N[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C)C1CCCCC1	4416.5	Semi standard non polar	33892256
Ximelagatran,2TBDMS,isomer #2	CCOC(=O)CN[C@@H](C(=O)N1CC[C@H]1C(=O)N(CC1=CC=C(/C(=N/O)N[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C)C1CCCCC1	4010.7	Standard non polar	33892256
Ximelagatran,2TBDMS,isomer #2	CCOC(=O)CN[C@@H](C(=O)N1CC[C@H]1C(=O)N(CC1=CC=C(/C(=N/O)N[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C)C1CCCCC1	5620.4	Standard polar	33892256
Ximelagatran,2TBDMS,isomer #3	CCOC(=O)CN[C@@H](C(=O)N1CC[C@H]1C(=O)NCC1=CC=C(/C(=N/O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1)C1CCCCC1	4500.3	Semi standard non polar	33892256
Ximelagatran,2TBDMS,isomer #3	CCOC(=O)CN[C@@H](C(=O)N1CC[C@H]1C(=O)NCC1=CC=C(/C(=N/O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1)C1CCCCC1	4085.8	Standard non polar	33892256
Ximelagatran,2TBDMS,isomer #3	CCOC(=O)CN[C@@H](C(=O)N1CC[C@H]1C(=O)NCC1=CC=C(/C(=N/O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1)C1CCCCC1	5590.7	Standard polar	33892256
Ximelagatran,2TBDMS,isomer #4	CCOC(=O)CN([C@@H](C(=O)N1CC[C@H]1C(=O)N(CC1=CC=C(/C(N)=N/O)C=C1)[Si](C)(C)C(C)(C)C)C1CCCCC1)[Si](C)(C)C(C)(C)C	4387.0	Semi standard non polar	33892256
Ximelagatran,2TBDMS,isomer #4	CCOC(=O)CN([C@@H](C(=O)N1CC[C@H]1C(=O)N(CC1=CC=C(/C(N)=N/O)C=C1)[Si](C)(C)C(C)(C)C)C1CCCCC1)[Si](C)(C)C(C)(C)C	3879.3	Standard non polar	33892256
Ximelagatran,2TBDMS,isomer #4	CCOC(=O)CN([C@@H](C(=O)N1CC[C@H]1C(=O)N(CC1=CC=C(/C(N)=N/O)C=C1)[Si](C)(C)C(C)(C)C)C1CCCCC1)[Si](C)(C)C(C)(C)C	6218.6	Standard polar	33892256
Ximelagatran,3TBDMS,isomer #1	CCOC(=O)CN([C@@H](C(=O)N1CC[C@H]1C(=O)N(CC1=CC=C(/C(=N/O)N[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C)C1CCCCC1)[Si](C)(C)C(C)(C)C	4565.0	Semi standard non polar	33892256
Ximelagatran,3TBDMS,isomer #1	CCOC(=O)CN([C@@H](C(=O)N1CC[C@H]1C(=O)N(CC1=CC=C(/C(=N/O)N[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C)C1CCCCC1)[Si](C)(C)C(C)(C)C	4093.3	Standard non polar	33892256
Ximelagatran,3TBDMS,isomer #1	CCOC(=O)CN([C@@H](C(=O)N1CC[C@H]1C(=O)N(CC1=CC=C(/C(=N/O)N[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C)C1CCCCC1)[Si](C)(C)C(C)(C)C	5342.5	Standard polar	33892256
Ximelagatran,3TBDMS,isomer #2	CCOC(=O)CN([C@@H](C(=O)N1CC[C@H]1C(=O)NCC1=CC=C(/C(=N/O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1)C1CCCCC1)[Si](C)(C)C(C)(C)C	4628.3	Semi standard non polar	33892256
Ximelagatran,3TBDMS,isomer #2	CCOC(=O)CN([C@@H](C(=O)N1CC[C@H]1C(=O)NCC1=CC=C(/C(=N/O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1)C1CCCCC1)[Si](C)(C)C(C)(C)C	4150.1	Standard non polar	33892256
Ximelagatran,3TBDMS,isomer #2	CCOC(=O)CN([C@@H](C(=O)N1CC[C@H]1C(=O)NCC1=CC=C(/C(=N/O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1)C1CCCCC1)[Si](C)(C)C(C)(C)C	5286.1	Standard polar	33892256
Ximelagatran,3TBDMS,isomer #3	CCOC(=O)CN[C@@H](C(=O)N1CC[C@H]1C(=O)N(CC1=CC=C(/C(=N/O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C)C1CCCCC1	4522.3	Semi standard non polar	33892256
Ximelagatran,3TBDMS,isomer #3	CCOC(=O)CN[C@@H](C(=O)N1CC[C@H]1C(=O)N(CC1=CC=C(/C(=N/O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C)C1CCCCC1	4197.4	Standard non polar	33892256
Ximelagatran,3TBDMS,isomer #3	CCOC(=O)CN[C@@H](C(=O)N1CC[C@H]1C(=O)N(CC1=CC=C(/C(=N/O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C)C1CCCCC1	5192.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Ximelagatran GC-MS (Non-derivatized) - 70eV, Positive	splash10-004j-4982400000-32fe628a565ad95d34f7	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ximelagatran 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 - Ximelagatran 10V, Positive-QTOF	splash10-03ka-0910600000-44563426df349abe783a	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ximelagatran 20V, Positive-QTOF	splash10-01ot-1900000000-993c6a2f4f07b4664b53	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ximelagatran 40V, Positive-QTOF	splash10-0002-2900000000-7463f581ac8e0bfad363	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ximelagatran 10V, Negative-QTOF	splash10-010r-1091600000-caf9b25e0e59704abc3d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ximelagatran 20V, Negative-QTOF	splash10-0i6r-1390100000-fa8587138131e92bfa4b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ximelagatran 40V, Negative-QTOF	splash10-0f6t-9780000000-e48b26348d984d96c2ca	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ximelagatran 10V, Positive-QTOF	splash10-00di-0011900000-d107c431444eff177ff3	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ximelagatran 20V, Positive-QTOF	splash10-00dj-0242900000-d014519f397e125b9c12	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ximelagatran 40V, Positive-QTOF	splash10-07cs-2910000000-1bde1af9d5c933ea620b	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ximelagatran 10V, Negative-QTOF	splash10-00di-0000900000-23339a41ce7aee480594	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ximelagatran 20V, Negative-QTOF	splash10-00di-0209400000-b804ae6102407413420b	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ximelagatran 40V, Negative-QTOF	splash10-0a4i-2691100000-8ca0829e1959417b49c4	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Ximelagatran Action Pathway		Not Available

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 DB04898	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB04898	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB04898

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

7848559

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Ximelagatran

METLIN ID

Not Available

PubChem Compound

656635

PDB ID

Not Available

ChEBI ID

65172

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

Eriksson H, Wahlander K, Gustafsson D, Welin LT, Frison L, Schulman S: A randomized, controlled, dose-guiding study of the oral direct thrombin inhibitor ximelagatran compared with standard therapy for the treatment of acute deep vein thrombosis: THRIVE I. J Thromb Haemost. 2003 Jan;1(1):41-7. [PubMed:12871538 ]
Francis CW, Berkowitz SD, Comp PC, Lieberman JR, Ginsberg JS, Paiement G, Peters GR, Roth AW, McElhattan J, Colwell CW Jr: Comparison of ximelagatran with warfarin for the prevention of venous thromboembolism after total knee replacement. N Engl J Med. 2003 Oct 30;349(18):1703-12. [PubMed:14585938 ]
Weitz JI: New anticoagulants for treatment of venous thromboembolism. Circulation. 2004 Aug 31;110(9 Suppl 1):I19-26. [PubMed:15339877 ]
Bergqvist D, Solhaug JH, Holmdahl L, Eriksson UG, Andersson M, Boberg B, Ogren M: Pharmacokinetics, preliminary efficacy and safety of subcutaneous melagatran and oral ximelagatran : a multicentre study of thromboprophylaxis in elective abdominal surgery. Clin Drug Investig. 2004;24(3):127-36. [PubMed:17516699 ]
Koscielny J, Kiesewetter H, Jorg I, Harenberg J: Ximelagatran for treatment and prophylaxis of recurrent events in deep vein thrombosis. Clin Appl Thromb Hemost. 2007 Jul;13(3):299-307. [PubMed:17636192 ]

Enzymes

Enzyme Details

1. Cytochrome P450 2C9

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

References

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

Showing metabocard for Ximelagatran (HMDB0015603)

MOL for HMDB0015603 (Ximelagatran)

3D MOL for HMDB0015603 (Ximelagatran)

3D SDF for HMDB0015603 (Ximelagatran)

3D-SDF for HMDB0015603 (Ximelagatran)

PDB for HMDB0015603 (Ximelagatran)

3D PDB for HMDB0015603 (Ximelagatran)

SMILES for HMDB0015603 (Ximelagatran)

INCHI for HMDB0015603 (Ximelagatran)

Structure for HMDB0015603 (Ximelagatran)

3D Structure for HMDB0015603 (Ximelagatran)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References