(2S)-2-(2-aminoacetamido)-5-carbamimidamido-N-[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]pentanamide

• ChemBase ID: 106289
• Molecular Formular: C18H21F3N6O4
• Molecular Mass: 442.3923496
• Monoisotopic Mass: 442.15763784
• SMILES: NCC(=O)N[C@@H](CCCNC(=N)N)C(=O)Nc1ccc2c(c1)oc(=O)cc2C(F)(F)F
• Canonical SMILES: NCC(=O)N[C@H](C(=O)Nc1ccc2c(c1)oc(=O)cc2C(F)(F)F)CCCNC(=N)N
• InChI: InChI=1S/C18H21F3N6O4/c19-18(20,21)11-7-15(29)31-13-6-9(3-4-10(11)13)26-16(30)12(27-14(28)8-22)2-1-5-25-17(23)24/h3-4,6-7,12H,1-2,5,8,22H2,(H,26,30)(H,27,28)(H4,23,24,25)/t12-/m0/s1
• InChIKey: KYBAIPUVVVKHPM-LBPRGKRZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-(2-aminoacetamido)-5-carbamimidamido-N-[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]pentanamide
• IUPAC Traditional name: (2S)-2-(2-aminoacetamido)-5-carbamimidamido-N-[2-oxo-4-(trifluoromethyl)chromen-7-yl]pentanamide
• Synonyms: Gly-Arg-AFC; GR-AFC; Gly-Arg-7-Amino-4-trifluoromethylcoumarin

Database IDs

• PubChem SID: 162105568
• PubChem CID: 25108511

CALCULATED PROPERTIES

• Acid pKa: 11.427342
• H Acceptors: 7
• H Donor: 6
• LogD (pH = 5.5): -5.336343
• LogD (pH = 7.4): -3.6446674
• Log P: -1.1525528
• Molar Refractivity: 115.709 cm^3
• Polarizability: 38.70641 Å^3
• Polar Surface Area: 172.42 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03AFC031

A fluorogenic substrate for Cathepsin C (DPP-I).

REFERENCES

• Hola-Jamriska, L. et al., Parasitology, 118:275 (1999).