(2S)-1-[(2R)-2-amino-3-phenylpropanoyl]-N-[(3S)-6-carbamimidamido-1-chloro-2-oxohexan-3-yl]pyrrolidine-2-carboxamide

• ChemBase ID: 4497
• Molecular Formular: C21H31ClN6O3
• Molecular Mass: 450.96224
• Monoisotopic Mass: 450.21461656
• SMILES: N[C@@H](C(=O)N1[C@H](C(=O)N[C@H](C(=O)CCl)CCCNC(=N)N)CCC1)Cc1ccccc1
• Canonical SMILES: ClCC(=O)[C@@H](NC(=O)[C@@H]1CCCN1C(=O)[C@@H](Cc1ccccc1)N)CCCNC(=N)N
• InChI: InChI=1S/C21H31ClN6O3/c22-13-18(29)16(8-4-10-26-21(24)25)27-19(30)17-9-5-11-28(17)20(31)15(23)12-14-6-2-1-3-7-14/h1-3,6-7,15-17H,4-5,8-13,23H2,(H,27,30)(H4,24,25,26)/t15-,16+,17+/m1/s1
• InChIKey: KWPACVJPAFGBEQ-IKGGRYGDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-1-[(2R)-2-amino-3-phenylpropanoyl]-N-[(3S)-6-carbamimidamido-1-chloro-2-oxohexan-3-yl]pyrrolidine-2-carboxamide
• IUPAC Traditional name: (2S)-1-[(2R)-2-amino-3-phenylpropanoyl]-N-[(3S)-6-carbamimidamido-1-chloro-2-oxohexan-3-yl]pyrrolidine-2-carboxamide
• Synonyms: D-phenylalanyl-N-[(1S)-4-{[amino(iminio)methyl]amino}-1-(chloroacetyl)butyl]-L-prolinamide; D-Phe-Pro-Arg-CMK; D-FPR-CMK; D-Phe-Pro-Arg-Chloromethylketone

Database IDs

• PubChem SID: 160967929; 99443312
• PubChem CID: 5311176; 46937029

CALCULATED PROPERTIES

JChem

• Acid pKa: 12.467068
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): -4.148671
• LogD (pH = 7.4): -2.5318344
• Log P: -0.09463055
• Molar Refractivity: 129.1303 cm^3
• Polarizability: 46.118343 Å^3
• Polar Surface Area: 154.4 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.33
• LOG S: -4.03
• Solubility (Water): 4.50e-02 g/l

DETAILS

MP Biomedicals - 03CK013

Highly effective irreversible inhibitor for Thrombin.

DrugBank - DB06841

Drug information: experimental

REFERENCES

• Kaiser, B. and Hauptmann, J., Cardiovasc. Drug. Rev., 10:71 (1992).
• Rahr, H. B. et al., Thromb. Res., 73:279 (1994).