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

• ChemBase ID: 170722
• Molecular Formular: C22H31N5O5
• Molecular Mass: 445.51204
• Monoisotopic Mass: 445.23251912
• SMILES: c1c(ccc(c1)CNC(=O)[C@@H]1CCN1C(=O)[C@@H](C1CCCCC1)NCC(=O)O)C(=N)NO
• Canonical SMILES: ONC(=N)c1ccc(cc1)CNC(=O)[C@@H]1CCN1C(=O)[C@@H](C1CCCCC1)NCC(=O)O
• InChI: InChI=1S/C22H31N5O5/c23-20(26-32)16-8-6-14(7-9-16)12-25-21(30)17-10-11-27(17)22(31)19(24-13-18(28)29)15-4-2-1-3-5-15/h6-9,15,17,19,24,32H,1-5,10-13H2,(H2,23,26)(H,25,30)(H,28,29)/t17-,19+/m0/s1
• InChIKey: NIPUHXUEGZHFLD-PKOBYXMFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{[(1R)-1-cyclohexyl-2-[(2S)-2-({[4-(N-hydroxycarbamimidoyl)phenyl]methyl}carbamoyl)azetidin-1-yl]-2-oxoethyl]amino}acetic acid
• IUPAC Traditional name: {[(1R)-1-cyclohexyl-2-[(2S)-2-({[4-(N-hydroxycarbamimidoyl)phenyl]methyl}carbamoyl)azetidin-1-yl]-2-oxoethyl]amino}acetic acid
• Synonyms: N-[(1R)-1-Cyclohexyl-2-[(2S)-2-[[[[4-[(hydroxyamino)iminomethyl]phenyl]methyl]amino]carbonyl]-1-azetidinyl]-2-oxoethyl]glycine; Melagatran Hydroxyamidine; N-Hydroxy Melagatran

Database IDs

• CAS Number: 192939-72-3
• PubChem SID: 164226632
• PubChem CID: 9889723

CALCULATED PROPERTIES

• Acid pKa: 3.1991851
• H Acceptors: 8
• H Donor: 6
• LogD (pH = 5.5): -3.245986
• LogD (pH = 7.4): -1.8447697
• Log P: -1.9376619
• Molar Refractivity: 137.9562 cm^3
• Polarizability: 45.33225 Å^3
• Polar Surface Area: 154.85 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: White Solid
• Melting Point: 210-212°C

Safety Information

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

DETAILS

Toronto Research Chemicals - H944585

An N-Hydroxyguanidine prodrug and intermediate in the preparation of Melagatran

REFERENCES

• Johansson, L., et al.: Clini.Pharmacokin., 42, 475 (2003)
• Gruenewald, S., et al.: J. Med. Chem., 51, 8173 (2003)
• Sjoegren, E., et al.: Drug Metab. Disposition, 37, 47 (2003)