4-[({[(1S)-4-carbamimidamido-1-{[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]carbamoyl}butyl]carbamoyl}methyl)carbamoyl]butanoic acid

• ChemBase ID: 106307
• Molecular Formular: C23H27F3N6O7
• Molecular Mass: 556.4916896
• Monoisotopic Mass: 556.18933189
• SMILES: NC(=N)NCCC[C@H](NC(=O)CNC(=O)CCCC(=O)O)C(=O)Nc1ccc2c(c1)oc(=O)cc2C(F)(F)F
• Canonical SMILES: O=C(N[C@H](C(=O)Nc1ccc2c(c1)oc(=O)cc2C(F)(F)F)CCCNC(=N)N)CNC(=O)CCCC(=O)O
• InChI: InChI=1S/C23H27F3N6O7/c24-23(25,26)14-10-20(37)39-16-9-12(6-7-13(14)16)31-21(38)15(3-2-8-29-22(27)28)32-18(34)11-30-17(33)4-1-5-19(35)36/h6-7,9-10,15H,1-5,8,11H2,(H,30,33)(H,31,38)(H,32,34)(H,35,36)(H4,27,28,29)/t15-/m0/s1
• InChIKey: XFNFYHXUQBLHFY-HNNXBMFYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[({[(1S)-4-carbamimidamido-1-{[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]carbamoyl}butyl]carbamoyl}methyl)carbamoyl]butanoic acid
• IUPAC Traditional name: 4-[({[(1S)-4-carbamimidamido-1-{[2-oxo-4-(trifluoromethyl)chromen-7-yl]carbamoyl}butyl]carbamoyl}methyl)carbamoyl]butanoic acid
• Synonyms: Glutaryl-Gly-Arg-AFC; Glutaryl-GR-AFC; Glutaryl-Gly-Arg-7-Amino-4-trifluoromethylcoumarin

Database IDs

• PubChem SID: 162105389
• PubChem CID: 25108528

CALCULATED PROPERTIES

• Acid pKa: 3.778089
• H Acceptors: 9
• H Donor: 7
• LogD (pH = 5.5): -2.2494125
• LogD (pH = 7.4): -2.242767
• Log P: -2.2428088
• Molar Refractivity: 140.6471 cm^3
• Polarizability: 48.283474 Å^3
• Polar Surface Area: 212.8 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03AFC050

A fluorogenic substrate for Urokinase.

REFERENCES

• Huseby, R.M. et al., Throm. Res., 10:679 (1977).