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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2020-02-26 21:39:40 UTC
HMDB IDHMDB0014447
Secondary Accession Numbers
  • HMDB14447
Metabolite Identification
Common NameTranexamic Acid
DescriptionTranexamic Acid is only found in individuals that have used or taken this drug. It is an antifibrinolytic hemostatic used in severe hemorrhage. [PubChem]Tranexamic acid competitively inhibits activation of plasminogen (via binding to the kringle domain), thereby reducing conversion of plasminogen to plasmin (fibrinolysin), an enzyme that degrades fibrin clots, fibrinogen, and other plasma proteins, including the procoagulant factors V and VIII. Tranexamic acid also directly inhibits plasmin activity, but higher doses are required than are needed to reduce plasmin formation.
Structure
Data?1582753180
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
Disposition

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point> 300 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility18.2 g/LNot Available
LogP0.3Not Available
Predicted 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
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0089-9300000000-a2879e3e82ff6def0490Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0fl3-5900000000-1a913e8fabe0428ad408Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052f-1900000000-1962eee8311ed50bfecaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0007-5900000000-b105f678c513b707dc19Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006t-9000000000-fbc5072e5d97dda1b7d7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-34da1f51d1ee749e3aabSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-08fr-1900000000-935430d5dd848105bc78Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01po-9400000000-087cae2e1f6218c2c233Spectrum
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
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 ]