ethyl 2-{[(1R)-1-(2H11)cyclohexyl-2-[(2S)-2-({[4-(N-hydroxycarbamimidoyl)phenyl]methyl}carbamoyl)azetidin-1-yl]-2-oxoethyl]amino}acetate

• ChemBase ID: 179601
• Molecular Formular: C24H35N5O5
• Molecular Mass: 473.5652
• Monoisotopic Mass: 473.26381925
• SMILES: c1c(ccc(c1)CNC(=O)[C@@H]1CCN1C(=O)[C@H](NCC(=O)OCC)C1CCCCC1)C(=N)NO
• Canonical SMILES: CCOC(=O)CN[C@@H](C(=O)N1CC[C@H]1C(=O)NCc1ccc(cc1)C(=N)NO)C1CCCCC1
• InChI: InChI=1S/C24H35N5O5/c1-2-34-20(30)15-26-21(17-6-4-3-5-7-17)24(32)29-13-12-19(29)23(31)27-14-16-8-10-18(11-9-16)22(25)28-33/h8-11,17,19,21,26,33H,2-7,12-15H2,1H3,(H2,25,28)(H,27,31)/t19-,21+/m0/s1
• InChIKey: ZXIBCJHYVWYIKI-PZJWPPBQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 2-{[(1R)-1-(^2H₁₁)cyclohexyl-2-[(2S)-2-({[4-(N-hydroxycarbamimidoyl)phenyl]methyl}carbamoyl)azetidin-1-yl]-2-oxoethyl]amino}acetate
• IUPAC Traditional name: ethyl 2-{[(1R)-1-(^2H₁₁)cyclohexyl-2-[(2S)-2-({[4-(N-hydroxycarbamimidoyl)phenyl]methyl}carbamoyl)azetidin-1-yl]-2-oxoethyl]amino}acetate
• Synonyms: N-[(1R)-1-(Cyclohexyl-d11)-2-[(2S)-2-[[[[4-[(hydroxyamino)iminomethyl]phenyl]methyl]amino]carbonyl]-1-azetidinyl]-2-oxoethyl]glycine Ethyl Ester; Exanta-d11; H 376/95-d11; Ximelagatran-d11

Database IDs

• PubChem SID: 164235511
• PubChem CID: 71753001

CALCULATED PROPERTIES

• Acid pKa: 14.631418
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): -1.0770072
• LogD (pH = 7.4): 0.62485135
• Log P: 0.93414026
• Molar Refractivity: 147.4739 cm^3
• Polarizability: 49.24348 Å^3
• Polar Surface Area: 143.85 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - X745002

An orally active direct thrombin inhibitor; prodrug of Melagatran. Antithrombotic.

REFERENCES

• Owens, P.K., et al.: J. Pharm. Biomed. Anal., 27, 587 (2002)
• Kalus, J.S., et al.: Expert Opin. Invest. Drugs, 13, 465 (2002)
• Boos, C.J., et al.: Eur. J. Int. Med., 16, 267 (2002)
• Cullberg, M., et al.: Clin. Pharmacol. Ther., 77, 279 (2002)