Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-06 15:16:52 UTC |
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Update Date | 2022-03-07 02:52:03 UTC |
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HMDB ID | HMDB0015603 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Ximelagatran |
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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. |
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Structure | CCOC(=O)CN[C@@H](C(=O)N1CC[C@H]1C(=O)NCC1=CC=C(C=C1)C(\N)=N\O)C1CCCCC1 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 |
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Synonyms | Value | Source |
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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 |
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Chemical Formula | C24H35N5O5 |
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Average Molecular Weight | 473.5652 |
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Monoisotopic Molecular Weight | 473.263819255 |
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IUPAC Name | ethyl 2-{[(1R)-1-cyclohexyl-2-[(2S)-2-[({4-[(Z)-N'-hydroxycarbamimidoyl]phenyl}methyl)carbamoyl]azetidin-1-yl]-2-oxoethyl]amino}acetate |
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Traditional Name | ximelagatran |
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CAS Registry Number | 192939-46-1 |
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SMILES | CCOC(=O)CN[C@@H](C(=O)N1CC[C@H]1C(=O)NCC1=CC=C(C=C1)C(\N)=N\O)C1CCCCC1 |
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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 |
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InChI Key | ZXIBCJHYVWYIKI-PZJWPPBQSA-N |
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Chemical Taxonomy |
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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. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Carboxylic acids and derivatives |
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Sub Class | Amino acids, peptides, and analogues |
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Direct Parent | Dipeptides |
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Alternative Parents | |
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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
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Molecular Framework | Aromatic heteromonocyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | |
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Role | Not Available |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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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 |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | | Show more...
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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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 |
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Spectra |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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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 SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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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 |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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Blood | Expected but not Quantified | Not Quantified | Not Available | Not Available | Taking drug identified by DrugBank entry DB04898 | | details | Urine | Expected but not Quantified | Not Quantified | Not Available | Not Available | Taking drug identified by DrugBank entry DB04898 | | details |
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Abnormal Concentrations |
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| Not Available |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | DB04898 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | Not Available |
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KNApSAcK ID | Not Available |
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Chemspider ID | 7848559 |
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KEGG Compound ID | Not Available |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Ximelagatran |
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METLIN ID | Not Available |
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PubChem Compound | 656635 |
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PDB ID | Not Available |
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ChEBI ID | 65172 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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Good Scents ID | Not Available |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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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 ]
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