| Record Information |
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| Version | 5.0 |
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| Status | Detected but not Quantified |
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| Creation Date | 2012-09-06 15:16:49 UTC |
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| Update Date | 2023-02-21 17:18:10 UTC |
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| HMDB ID | HMDB0014447 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | Tranexamic Acid |
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| Description | Tranexamic Acid, also known as tranexmate or acido tranexamico, belongs to the class of organic compounds known as amino acids. These are organic compounds that contain at least one carboxyl group and one amino group. Tranexamic Acid is a drug which is used for use in patients with hemophilia for short term use (two to eight days) to reduce or prevent hemorrhage and reduce the need for replacement therapy during and following tooth extraction. it can also be used for excessive bleeding in menstruation, surgery, or trauma cases. Tranexamic Acid is only found in individuals that have used or taken this drug. Tranexamic Acid is a very strong basic compound (based on its pKa). In humans, tranexamic Acid is involved in tranexamic acid action pathway. It is an antifibrinolytic hemostatic used in severe hemorrhage. Oral LD50 in mice is >10 gm/kg. In patients with hereditary angioedema, inhibition of the formation and activity of plasmin by tranexamic acid may prevent attacks of angioedema by decreasing plasmin-induced activation of the first complement protein (C1). Tranexamic acid in a concentration of 1 mg per mL does not aggregate platelets in vitro. Tranexamic acid is about 10 times more potent in vitro than aminocaproic acid. |
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| Structure | NC[C@H]1CC[C@@H](CC1)C(O)=O InChI=1S/C8H15NO2/c9-5-6-1-3-7(4-2-6)8(10)11/h6-7H,1-5,9H2,(H,10,11)/t6-,7- |
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| Synonyms | | Value | Source |
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| Acide tranexamique | ChEBI | | Acido tranexamico | ChEBI | | Acidum tranexamicum | ChEBI | | Cyklokapron | ChEBI | | Tranexamsaeure | ChEBI | | Tranexmic acid | ChEBI | | Tranhexamic acid | ChEBI | | trans AMCHA | ChEBI | | trans-4-(Aminomethyl)cyclohexanecarboxylic acid | ChEBI | | trans-4-AMINOMETHYLCYCLOHEXANE-1-carboxylIC ACID | ChEBI | | trans-Amcha | ChEBI | | trans-Tranexamic acid | ChEBI | | Tranexmate | Generator | | Tranhexamate | Generator | | trans-4-(Aminomethyl)cyclohexanecarboxylate | Generator | | trans-4-AMINOMETHYLCYCLOHEXANE-1-carboxylate | Generator | | trans-Tranexamate | Generator | | Tranexamate | Generator |
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| Chemical Formula | C8H15NO2 |
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| Average Molecular Weight | 157.2102 |
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| Monoisotopic Molecular Weight | 157.110278729 |
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| IUPAC Name | (1r,4r)-4-(aminomethyl)cyclohexane-1-carboxylic acid |
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| Traditional Name | tranexamic acid |
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| CAS Registry Number | 1197-18-8 |
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| SMILES | NC[C@H]1CC[C@@H](CC1)C(O)=O |
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| InChI Identifier | InChI=1S/C8H15NO2/c9-5-6-1-3-7(4-2-6)8(10)11/h6-7H,1-5,9H2,(H,10,11)/t6-,7- |
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| InChI Key | GYDJEQRTZSCIOI-LJGSYFOKSA-N |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as amino acids. These are organic compounds that contain at least one carboxyl group and one amino group. |
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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 | Amino acids |
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| Alternative Parents | |
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| Substituents | - Amino acid
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Organic nitrogen compound
- Organic oxygen compound
- Organopnictogen compound
- Organic oxide
- Hydrocarbon derivative
- Primary amine
- Organooxygen compound
- Organonitrogen compound
- Primary aliphatic amine
- Carbonyl group
- Amine
- Aliphatic homomonocyclic compound
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| Molecular Framework | Aliphatic homomonocyclic 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 | > 300 °C | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | 18.2 g/L | Not Available | | LogP | 0.3 | Not Available |
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| Experimental Chromatographic Properties | Not Available |
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| Predicted Molecular Properties | |
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| Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Retention Times Underivatized| Chromatographic Method | Retention Time | Reference |
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| 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. | 1.48 minutes | 32390414 | | Predicted by Siyang on May 30, 2022 | 9.2555 minutes | 33406817 | | Predicted by Siyang using ReTip algorithm on June 8, 2022 | 5.99 minutes | 32390414 | | AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid | 302.0 seconds | 40023050 | | Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid | 699.5 seconds | 40023050 | | Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid | 264.1 seconds | 40023050 | | Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid | 90.3 seconds | 40023050 | | Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid | 170.9 seconds | 40023050 | | RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 136.5 seconds | 40023050 | | Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid | 247.6 seconds | 40023050 | | BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid | 278.2 seconds | 40023050 | | HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate) | 759.7 seconds | 40023050 | | UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid | 632.6 seconds | 40023050 | | BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid | 165.1 seconds | 40023050 | | UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid | 717.4 seconds | 40023050 | | SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 160.3 seconds | 40023050 | | RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 223.4 seconds | 40023050 | | MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate | 694.8 seconds | 40023050 | | KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA | 388.0 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 | 328.8 seconds | 40023050 |
Predicted Kovats Retention IndicesUnderivatizedDerivatized| Derivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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| Tranexamic Acid,1TMS,isomer #1 | C[Si](C)(C)OC(=O)[C@H]1CC[C@H](CN)CC1 | 1514.8 | Semi standard non polar | 33892256 | | Tranexamic Acid,1TMS,isomer #2 | C[Si](C)(C)NC[C@H]1CC[C@H](C(=O)O)CC1 | 1645.5 | Semi standard non polar | 33892256 | | Tranexamic Acid,2TMS,isomer #1 | C[Si](C)(C)NC[C@H]1CC[C@H](C(=O)O[Si](C)(C)C)CC1 | 1648.9 | Semi standard non polar | 33892256 | | Tranexamic Acid,2TMS,isomer #1 | C[Si](C)(C)NC[C@H]1CC[C@H](C(=O)O[Si](C)(C)C)CC1 | 1684.2 | Standard non polar | 33892256 | | Tranexamic Acid,2TMS,isomer #1 | C[Si](C)(C)NC[C@H]1CC[C@H](C(=O)O[Si](C)(C)C)CC1 | 1968.2 | Standard polar | 33892256 | | Tranexamic Acid,2TMS,isomer #2 | C[Si](C)(C)N(C[C@H]1CC[C@H](C(=O)O)CC1)[Si](C)(C)C | 1877.1 | Semi standard non polar | 33892256 | | Tranexamic Acid,2TMS,isomer #2 | C[Si](C)(C)N(C[C@H]1CC[C@H](C(=O)O)CC1)[Si](C)(C)C | 1827.4 | Standard non polar | 33892256 | | Tranexamic Acid,2TMS,isomer #2 | C[Si](C)(C)N(C[C@H]1CC[C@H](C(=O)O)CC1)[Si](C)(C)C | 2220.5 | Standard polar | 33892256 | | Tranexamic Acid,3TMS,isomer #1 | C[Si](C)(C)OC(=O)[C@H]1CC[C@H](CN([Si](C)(C)C)[Si](C)(C)C)CC1 | 1841.6 | Semi standard non polar | 33892256 | | Tranexamic Acid,3TMS,isomer #1 | C[Si](C)(C)OC(=O)[C@H]1CC[C@H](CN([Si](C)(C)C)[Si](C)(C)C)CC1 | 1852.0 | Standard non polar | 33892256 | | Tranexamic Acid,3TMS,isomer #1 | C[Si](C)(C)OC(=O)[C@H]1CC[C@H](CN([Si](C)(C)C)[Si](C)(C)C)CC1 | 1904.7 | Standard polar | 33892256 | | Tranexamic Acid,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)[C@H]1CC[C@H](CN)CC1 | 1734.6 | Semi standard non polar | 33892256 | | Tranexamic Acid,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)NC[C@H]1CC[C@H](C(=O)O)CC1 | 1901.0 | Semi standard non polar | 33892256 | | Tranexamic Acid,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)NC[C@H]1CC[C@H](C(=O)O[Si](C)(C)C(C)(C)C)CC1 | 2093.5 | Semi standard non polar | 33892256 | | Tranexamic Acid,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)NC[C@H]1CC[C@H](C(=O)O[Si](C)(C)C(C)(C)C)CC1 | 2141.5 | Standard non polar | 33892256 | | Tranexamic Acid,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)NC[C@H]1CC[C@H](C(=O)O[Si](C)(C)C(C)(C)C)CC1 | 2196.2 | Standard polar | 33892256 | | Tranexamic Acid,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N(C[C@H]1CC[C@H](C(=O)O)CC1)[Si](C)(C)C(C)(C)C | 2280.0 | Semi standard non polar | 33892256 | | Tranexamic Acid,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N(C[C@H]1CC[C@H](C(=O)O)CC1)[Si](C)(C)C(C)(C)C | 2248.2 | Standard non polar | 33892256 | | Tranexamic Acid,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N(C[C@H]1CC[C@H](C(=O)O)CC1)[Si](C)(C)C(C)(C)C | 2343.0 | Standard polar | 33892256 | | Tranexamic Acid,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)[C@H]1CC[C@H](CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CC1 | 2491.0 | Semi standard non polar | 33892256 | | Tranexamic Acid,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)[C@H]1CC[C@H](CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CC1 | 2487.3 | Standard non polar | 33892256 | | Tranexamic Acid,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)[C@H]1CC[C@H](CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CC1 | 2245.2 | Standard polar | 33892256 |
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| GC-MS Spectra| Spectrum Type | Description | Splash Key | Deposition Date | Source | View |
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| Predicted GC-MS | Predicted GC-MS Spectrum - Tranexamic Acid GC-MS (Non-derivatized) - 70eV, Positive | splash10-0089-9300000000-a2879e3e82ff6def0490 | 2017-08-28 | Wishart Lab | View Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - Tranexamic Acid GC-MS (1 TMS) - 70eV, Positive | splash10-0fl3-5900000000-1a913e8fabe0428ad408 | 2017-10-06 | Wishart Lab | View Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - Tranexamic Acid 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 |
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| Experimental LC-MS/MS | LC-MS/MS Spectrum - Tranexamic Acid 35V, Positive-QTOF | splash10-0002-9000000000-112fa48ed4ac17a5179e | 2021-09-20 | HMDB team, MONA | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tranexamic Acid 10V, Positive-QTOF | splash10-052f-1900000000-1962eee8311ed50bfeca | 2017-07-25 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tranexamic Acid 20V, Positive-QTOF | splash10-0007-5900000000-b105f678c513b707dc19 | 2017-07-25 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tranexamic Acid 40V, Positive-QTOF | splash10-006t-9000000000-fbc5072e5d97dda1b7d7 | 2017-07-25 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tranexamic Acid 10V, Negative-QTOF | splash10-0a4i-0900000000-34da1f51d1ee749e3aab | 2017-07-26 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tranexamic Acid 20V, Negative-QTOF | splash10-08fr-1900000000-935430d5dd848105bc78 | 2017-07-26 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tranexamic Acid 40V, Negative-QTOF | splash10-01po-9400000000-087cae2e1f6218c2c233 | 2017-07-26 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tranexamic Acid 10V, Positive-QTOF | splash10-0005-9600000000-9e76318f98dca56cd89e | 2021-09-24 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tranexamic Acid 20V, Positive-QTOF | splash10-0005-9800000000-4d79429c64e7d679fcfb | 2021-09-24 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tranexamic Acid 40V, Positive-QTOF | splash10-052g-9000000000-c75f4309991571d358f2 | 2021-09-24 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tranexamic Acid 10V, Negative-QTOF | splash10-0a4i-0900000000-0f7129c598f6efd38657 | 2021-09-24 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tranexamic Acid 20V, Negative-QTOF | splash10-0bt9-1900000000-aff35fbd5bfb31783171 | 2021-09-24 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tranexamic Acid 40V, Negative-QTOF | splash10-0006-9800000000-78de9bf4dc31cb5308a8 | 2021-09-24 | Wishart Lab | View Spectrum |
NMR Spectra| Spectrum Type | Description | Deposition Date | Source | View |
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| Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum |
IR Spectra| Spectrum Type | Description | Deposition Date | Source | View |
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| Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-) | 2023-02-03 | FELIX lab | View Spectrum | | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+) | 2023-02-03 | FELIX lab | View Spectrum | | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+) | 2023-02-03 | FELIX lab | View Spectrum |
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| Disease References | | Ulcerative colitis |
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- Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Nucleic Acids Res. 2011 Jan;39(Database issue):D1035-41. doi: 10.1093/nar/gkq1126. Epub 2010 Nov 8. [PubMed:21059682 ]
- Almer S, Andersson T, Strom M: Pharmacokinetics of tranexamic acid in patients with ulcerative colitis and in healthy volunteers after the single instillation of 2 g rectally. J Clin Pharmacol. 1992 Jan;32(1):49-54. [PubMed:1740537 ]
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