(1s,4s)-4-(aminomethyl)cyclohexane-1-carboxylic acid

• ChemBase ID: 178808
• Molecular Formular: C8H15NO2
• Molecular Mass: 157.2102
• Monoisotopic Mass: 157.11027873
• SMILES: C1C[C@@H](CC[C@@H]1C(=O)O)CN
• Canonical SMILES: NC[C@@H]1CC[C@@H](CC1)C(=O)O
• InChI: 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+
• InChIKey: GYDJEQRTZSCIOI-KNVOCYPGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1s,4s)-4-(aminomethyl)cyclohexane-1-carboxylic acid
• IUPAC Traditional name: tranexamic acid
• Synonyms: cis-4-(Aminomethyl)cyclohexanecarboxylic Acid; cis-4-(Aminomethyl)-1-cyclohexanecarboxylic Acid; cis-AMCHA; cis-Tranexamic Acid

Database IDs

• CAS Number: 1197-17-7
• PubChem SID: 164234718
• PubChem CID: 5526

CALCULATED PROPERTIES

• Acid pKa: 4.5582533
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -1.5895343
• LogD (pH = 7.4): -1.5519825
• Log P: -1.5523915
• Molar Refractivity: 41.9037 cm^3
• Polarizability: 16.785397 Å^3
• Polar Surface Area: 63.32 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White Solid
• Melting Point: 226-228°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - T714500

Antifibrinolytic agent; blocks lysine binding sites of plasminogen. Hemostatic.

REFERENCES

• Andersson, et al.: Scand. J. Haematol. 2, 230 (1965)
• Melander, B., et al.: Acta Pharmacol. Toxicol., 22, 340 (1965)
• Bonnar, J., et al.: Br. Med. J., 313, 579 (1965)
• Dunn, C.J., et al.: Drugs, 57, 1005 (1965)