2-{[(1R)-2-[(2S)-2-{[(4-carbamimidoylphenyl)methyl]carbamoyl}azetidin-1-yl]-1-cyclohexyl-2-oxoethyl]amino}acetic acid

• ChemBase ID: 172615
• Molecular Formular: C22H31N5O4
• Molecular Mass: 429.51264
• Monoisotopic Mass: 429.2376045
• SMILES: c1c(ccc(c1)CNC(=O)[C@@H]1CCN1C(=O)[C@@H](C1CCCCC1)NCC(=O)O)C(=N)N
• Canonical SMILES: OC(=O)CN[C@@H](C(=O)N1CC[C@H]1C(=O)NCc1ccc(cc1)C(=N)N)C1CCCCC1
• InChI: InChI=1S/C22H31N5O4/c23-20(24)16-8-6-14(7-9-16)12-26-21(30)17-10-11-27(17)22(31)19(25-13-18(28)29)15-4-2-1-3-5-15/h6-9,15,17,19,25H,1-5,10-13H2,(H3,23,24)(H,26,30)(H,28,29)/t17-,19+/m0/s1
• InChIKey: DKWNMCUOEDMMIN-PKOBYXMFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{[(1R)-2-[(2S)-2-{[(4-carbamimidoylphenyl)methyl]carbamoyl}azetidin-1-yl]-1-cyclohexyl-2-oxoethyl]amino}acetic acid
• IUPAC Traditional name: {[(1R)-2-[(2S)-2-{[(4-carbamimidoylphenyl)methyl]carbamoyl}azetidin-1-yl]-1-cyclohexyl-2-oxoethyl]amino}acetic acid
• Synonyms: N-[(1R)-2-[(2S)-2-[[[[4-(Aminoiminomethyl)phenyl]methyl]amino]carbonyl]-1-azetidinyl]-1-cyclohexyl-2-oxoethyl]glycine; H-319/68; Melagatran

Database IDs

• CAS Number: 159776-70-2
• PubChem SID: 164228525
• PubChem CID: 183797

CALCULATED PROPERTIES

• Acid pKa: 3.1992116
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): -3.4044096
• LogD (pH = 7.4): -1.7261133
• Log P: -1.2909487
• Molar Refractivity: 125.6988 cm^3
• Polarizability: 44.68033 Å^3
• Polar Surface Area: 148.61 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: White Solid
• Melting Point: 172-177°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - M208450

Synthetic thrombin inhibitor. Thrombin mutant anticoagulant antagonist. Antithrombotic.

REFERENCES

• Dewanjee, M., et al.: J. Nucl. Med., 22, 981 (1981)
• Goodman, S., et al.: J. Biomed. Mater. Res., 45, 240 (1981)
• Carlsson, S., et al.: Thromb. Res., 115, 9 (1981)