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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2023-02-21 17:18:10 UTC
HMDB IDHMDB0014447
Secondary Accession Numbers
  • HMDB14447
Metabolite Identification
Common NameTranexamic Acid
DescriptionTranexamic 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.
Structure
Data?1676999890
Synonyms
ValueSource
Acide tranexamiqueChEBI
Acido tranexamicoChEBI
Acidum tranexamicumChEBI
CyklokapronChEBI
TranexamsaeureChEBI
Tranexmic acidChEBI
Tranhexamic acidChEBI
trans AMCHAChEBI
trans-4-(Aminomethyl)cyclohexanecarboxylic acidChEBI
trans-4-AMINOMETHYLCYCLOHEXANE-1-carboxylIC ACIDChEBI
trans-AmchaChEBI
trans-Tranexamic acidChEBI
TranexmateGenerator
TranhexamateGenerator
trans-4-(Aminomethyl)cyclohexanecarboxylateGenerator
trans-4-AMINOMETHYLCYCLOHEXANE-1-carboxylateGenerator
trans-TranexamateGenerator
TranexamateGenerator
Chemical FormulaC8H15NO2
Average Molecular Weight157.2102
Monoisotopic Molecular Weight157.110278729
IUPAC Name(1r,4r)-4-(aminomethyl)cyclohexane-1-carboxylic acid
Traditional Nametranexamic acid
CAS Registry Number1197-18-8
SMILES
NC[C@H]1CC[C@@H](CC1)C(O)=O
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-
InChI KeyGYDJEQRTZSCIOI-LJGSYFOKSA-N
Chemical Taxonomy
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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAmino acids
Alternative Parents
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
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point> 300 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility18.2 g/LNot Available
LogP0.3Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility18.2 g/LALOGPS
logP-1.4ALOGPS
logP-1.6ChemAxon
logS-0.94ALOGPS
pKa (Strongest Acidic)4.56ChemAxon
pKa (Strongest Basic)10.22ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity41.9 m³·mol⁻¹ChemAxon
Polarizability17.28 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+134.87731661259
DarkChem[M-H]-132.96931661259
DeepCCS[M+H]+134.35830932474
DeepCCS[M-H]-130.74930932474
DeepCCS[M-2H]-167.9330932474
DeepCCS[M+Na]+143.46830932474
AllCCS[M+H]+135.932859911
AllCCS[M+H-H2O]+131.632859911
AllCCS[M+NH4]+139.932859911
AllCCS[M+Na]+141.032859911
AllCCS[M-H]-136.832859911
AllCCS[M+Na-2H]-138.332859911
AllCCS[M+HCOO]-140.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Tranexamic AcidNC[C@H]1CC[C@@H](CC1)C(O)=O2252.4Standard polar33892256
Tranexamic AcidNC[C@H]1CC[C@@H](CC1)C(O)=O1515.1Standard non polar33892256
Tranexamic AcidNC[C@H]1CC[C@@H](CC1)C(O)=O1490.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Tranexamic Acid,1TMS,isomer #1C[Si](C)(C)OC(=O)[C@H]1CC[C@H](CN)CC11514.8Semi standard non polar33892256
Tranexamic Acid,1TMS,isomer #2C[Si](C)(C)NC[C@H]1CC[C@H](C(=O)O)CC11645.5Semi standard non polar33892256
Tranexamic Acid,2TMS,isomer #1C[Si](C)(C)NC[C@H]1CC[C@H](C(=O)O[Si](C)(C)C)CC11648.9Semi standard non polar33892256
Tranexamic Acid,2TMS,isomer #1C[Si](C)(C)NC[C@H]1CC[C@H](C(=O)O[Si](C)(C)C)CC11684.2Standard non polar33892256
Tranexamic Acid,2TMS,isomer #1C[Si](C)(C)NC[C@H]1CC[C@H](C(=O)O[Si](C)(C)C)CC11968.2Standard polar33892256
Tranexamic Acid,2TMS,isomer #2C[Si](C)(C)N(C[C@H]1CC[C@H](C(=O)O)CC1)[Si](C)(C)C1877.1Semi standard non polar33892256
Tranexamic Acid,2TMS,isomer #2C[Si](C)(C)N(C[C@H]1CC[C@H](C(=O)O)CC1)[Si](C)(C)C1827.4Standard non polar33892256
Tranexamic Acid,2TMS,isomer #2C[Si](C)(C)N(C[C@H]1CC[C@H](C(=O)O)CC1)[Si](C)(C)C2220.5Standard polar33892256
Tranexamic Acid,3TMS,isomer #1C[Si](C)(C)OC(=O)[C@H]1CC[C@H](CN([Si](C)(C)C)[Si](C)(C)C)CC11841.6Semi standard non polar33892256
Tranexamic Acid,3TMS,isomer #1C[Si](C)(C)OC(=O)[C@H]1CC[C@H](CN([Si](C)(C)C)[Si](C)(C)C)CC11852.0Standard non polar33892256
Tranexamic Acid,3TMS,isomer #1C[Si](C)(C)OC(=O)[C@H]1CC[C@H](CN([Si](C)(C)C)[Si](C)(C)C)CC11904.7Standard polar33892256
Tranexamic Acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@H]1CC[C@H](CN)CC11734.6Semi standard non polar33892256
Tranexamic Acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC[C@H]1CC[C@H](C(=O)O)CC11901.0Semi standard non polar33892256
Tranexamic Acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC[C@H]1CC[C@H](C(=O)O[Si](C)(C)C(C)(C)C)CC12093.5Semi standard non polar33892256
Tranexamic Acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC[C@H]1CC[C@H](C(=O)O[Si](C)(C)C(C)(C)C)CC12141.5Standard non polar33892256
Tranexamic Acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC[C@H]1CC[C@H](C(=O)O[Si](C)(C)C(C)(C)C)CC12196.2Standard polar33892256
Tranexamic Acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C[C@H]1CC[C@H](C(=O)O)CC1)[Si](C)(C)C(C)(C)C2280.0Semi standard non polar33892256
Tranexamic Acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C[C@H]1CC[C@H](C(=O)O)CC1)[Si](C)(C)C(C)(C)C2248.2Standard non polar33892256
Tranexamic Acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C[C@H]1CC[C@H](C(=O)O)CC1)[Si](C)(C)C(C)(C)C2343.0Standard polar33892256
Tranexamic Acid,3TBDMS,isomer #1CC(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)CC12491.0Semi standard non polar33892256
Tranexamic Acid,3TBDMS,isomer #1CC(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)CC12487.3Standard non polar33892256
Tranexamic Acid,3TBDMS,isomer #1CC(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)CC12245.2Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Tranexamic Acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0089-9300000000-a2879e3e82ff6def04902017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tranexamic Acid GC-MS (1 TMS) - 70eV, Positivesplash10-0fl3-5900000000-1a913e8fabe0428ad4082017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tranexamic Acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Tranexamic Acid 35V, Positive-QTOFsplash10-0002-9000000000-112fa48ed4ac17a5179e2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tranexamic Acid 10V, Positive-QTOFsplash10-052f-1900000000-1962eee8311ed50bfeca2017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tranexamic Acid 20V, Positive-QTOFsplash10-0007-5900000000-b105f678c513b707dc192017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tranexamic Acid 40V, Positive-QTOFsplash10-006t-9000000000-fbc5072e5d97dda1b7d72017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tranexamic Acid 10V, Negative-QTOFsplash10-0a4i-0900000000-34da1f51d1ee749e3aab2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tranexamic Acid 20V, Negative-QTOFsplash10-08fr-1900000000-935430d5dd848105bc782017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tranexamic Acid 40V, Negative-QTOFsplash10-01po-9400000000-087cae2e1f6218c2c2332017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tranexamic Acid 10V, Positive-QTOFsplash10-0005-9600000000-9e76318f98dca56cd89e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tranexamic Acid 20V, Positive-QTOFsplash10-0005-9800000000-4d79429c64e7d679fcfb2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tranexamic Acid 40V, Positive-QTOFsplash10-052g-9000000000-c75f4309991571d358f22021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tranexamic Acid 10V, Negative-QTOFsplash10-0a4i-0900000000-0f7129c598f6efd386572021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tranexamic Acid 20V, Negative-QTOFsplash10-0bt9-1900000000-aff35fbd5bfb317831712021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tranexamic Acid 40V, Negative-QTOFsplash10-0006-9800000000-78de9bf4dc31cb5308a82021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot AvailableNot AvailableUlcerative colitis details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedUlcerative colitis details
Associated Disorders and Diseases
Disease References
Ulcerative colitis
  1. 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 ]
  2. 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 ]
Associated OMIM IDsNone
DrugBank IDDB00302
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID10482000
KEGG Compound IDC12535
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTranexamic_Acid
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID48669
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in serine-type endopeptidase activity
Specific function:
Angiostatin is an angiogenesis inhibitor that blocks neovascularization and growth of experimental primary and metastatic tumors in vivo
Gene Name:
PLG
Uniprot ID:
P00747
Molecular weight:
90568.4
References
  1. Dunn CJ, Goa KL: Tranexamic acid: a review of its use in surgery and other indications. Drugs. 1999 Jun;57(6):1005-32. [PubMed:10400410 ]
  2. Marti DN, Schaller J, Llinas M: Solution structure and dynamics of the plasminogen kringle 2-AMCHA complex: 3(1)-helix in homologous domains. Biochemistry. 1999 Nov 30;38(48):15741-55. [PubMed:10625440 ]
  3. Jansen AJ, Andreica S, Claeys M, D'Haese J, Camu F, Jochmans K: Use of tranexamic acid for an effective blood conservation strategy after total knee arthroplasty. Br J Anaesth. 1999 Oct;83(4):596-601. [PubMed:10673876 ]
  4. Bangert K, Thorsen S: Assay of functional plasminogen in rat plasma applicable to experimental studies of thrombolysis. Thromb Haemost. 2000 Aug;84(2):299-306. [PubMed:10959704 ]
  5. Hanson AJ, Quinn MT: Effect of fibrin sealant composition on human neutrophil chemotaxis. J Biomed Mater Res. 2002 Sep 5;61(3):474-81. [PubMed:12115473 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]