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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2017-12-07 02:45:44 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
Thumb
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
TranexamateGenerator
TranexmateGenerator
TranhexamateGenerator
trans-4-(Aminomethyl)cyclohexanecarboxylateGenerator
trans-4-AMINOMETHYLCYCLOHEXANE-1-carboxylateGenerator
trans-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
DescriptionThis compound belongs to the class of chemical entities known as amino acids. These are organic compounds that contain at least one carboxyl group and one amino group.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic acids and derivatives
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:

  Subcellular:

  Biofluid and excreta:

  Cell and elements:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Role

Industrial application:

  Pharmaceutical industry:

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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0089-9300000000-a2879e3e82ff6def0490View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0fl3-5900000000-1a913e8fabe0428ad408View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052f-1900000000-1962eee8311ed50bfecaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0007-5900000000-b105f678c513b707dc19View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006t-9000000000-fbc5072e5d97dda1b7d7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-34da1f51d1ee749e3aabView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-08fr-1900000000-935430d5dd848105bc78View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01po-9400000000-087cae2e1f6218c2c233View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
Tranexamic Acid PathwayPw000309Pw000309 greyscalePw000309 simpleNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected but not Quantified Not AvailableNot AvailableNormal details
UrineDetected but not Quantified Not SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected but not Quantified Not AvailableNot AvailableUlcerative colitis details
UrineDetected but not Quantified Not SpecifiedNot SpecifiedUlcerative colitis details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00302
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB 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 IDAMH
ChEBI ID48669
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 ]