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

• ChemBase ID: 106296
• Molecular Formular: C22H30F3N9O4
• Molecular Mass: 541.5267096
• Monoisotopic Mass: 541.23728515
• SMILES: N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CCCNC(=N)N)C(=O)Nc1ccc2c(c1)oc(=O)cc2C(F)(F)F
• Canonical SMILES: NC(=N)NCCC[C@@H](C(=O)Nc1ccc2c(c1)oc(=O)cc2C(F)(F)F)NC(=O)[C@H](CCCNC(=N)N)N
• InChI: InChI=1S/C22H30F3N9O4/c23-22(24,25)13-10-17(35)38-16-9-11(5-6-12(13)16)33-19(37)15(4-2-8-32-21(29)30)34-18(36)14(26)3-1-7-31-20(27)28/h5-6,9-10,14-15H,1-4,7-8,26H2,(H,33,37)(H,34,36)(H4,27,28,31)(H4,29,30,32)/t14-,15-/m0/s1
• InChIKey: CLZUQSCLZFVWAX-GJZGRUSLSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• PubChem SID: 162105385
• PubChem CID: 25108517

CALCULATED PROPERTIES

• Acid pKa: 11.419873
• H Acceptors: 10
• H Donor: 9
• LogD (pH = 5.5): -8.0349865
• LogD (pH = 7.4): -6.351943
• Log P: -1.6078002
• Molar Refractivity: 153.6287 cm^3
• Polarizability: 49.052208 Å^3
• Polar Surface Area: 234.32 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03AFC038

VERY HYGROSCOPIC. Keep in desiccator. A fluorogenic substrate for DPP-III.

REFERENCES

• Manhtle, D. et al., Biochem., 211:567 (1983).