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

• ChemBase ID: 106401
• Molecular Formular: C22H33N9O4
• Molecular Mass: 487.55532
• Monoisotopic Mass: 487.26555058
• SMILES: Cc1cc(=O)oc2c1ccc(NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H](N)CCCNC(=N)N)c2
• Canonical SMILES: NC(=N)NCCC[C@@H](C(=O)Nc1ccc2c(c1)oc(=O)cc2C)NC(=O)[C@H](CCCNC(=N)N)N
• InChI: InChI=1S/C22H33N9O4/c1-12-10-18(32)35-17-11-13(6-7-14(12)17)30-20(34)16(5-3-9-29-22(26)27)31-19(33)15(23)4-2-8-28-21(24)25/h6-7,10-11,15-16H,2-5,8-9,23H2,1H3,(H,30,34)(H,31,33)(H4,24,25,28)(H4,26,27,29)/t15-,16-/m0/s1
• InChIKey: GYCFVTDDPZJPRH-HOTGVXAUSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• PubChem SID: 162105621
• PubChem CID: 24801919

CALCULATED PROPERTIES

• Acid pKa: 12.580238
• H Acceptors: 10
• H Donor: 9
• LogD (pH = 5.5): -8.399407
• LogD (pH = 7.4): -6.7183924
• Log P: -1.9286585
• Molar Refractivity: 152.6962 cm^3
• Polarizability: 49.647938 Å^3
• Polar Surface Area: 234.32 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03AMC038

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

REFERENCES

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