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

• ChemBase ID: 106395
• Molecular Formular: C18H24N6O4
• Molecular Mass: 388.42096
• Monoisotopic Mass: 388.18590328
• SMILES: Cc1cc(=O)oc2c1ccc(NC(=O)[C@H](CCCNC(=N)N)NC(=O)CN)c2
• Canonical SMILES: NCC(=O)N[C@H](C(=O)Nc1ccc2c(c1)oc(=O)cc2C)CCCNC(=N)N
• InChI: InChI=1S/C18H24N6O4/c1-10-7-16(26)28-14-8-11(4-5-12(10)14)23-17(27)13(24-15(25)9-19)3-2-6-22-18(20)21/h4-5,7-8,13H,2-3,6,9,19H2,1H3,(H,23,27)(H,24,25)(H4,20,21,22)/t13-/m0/s1
• InChIKey: JNTASUHAFOHMQK-ZDUSSCGKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-(2-aminoacetamido)-5-carbamimidamido-N-(4-methyl-2-oxo-2H-chromen-7-yl)pentanamide
• IUPAC Traditional name: (2S)-2-(2-aminoacetamido)-5-carbamimidamido-N-(4-methyl-2-oxochromen-7-yl)pentanamide
• Synonyms: Gly-Arg-AMC; GR-AMC; Gly-Arg-7-Amino-4-Methylcoumarin

Database IDs

• PubChem SID: 162105434
• PubChem CID: 493582

CALCULATED PROPERTIES

• Acid pKa: 12.340301
• H Acceptors: 7
• H Donor: 6
• LogD (pH = 5.5): -5.7007847
• LogD (pH = 7.4): -4.012271
• Log P: -1.4390645
• Molar Refractivity: 114.7765 cm^3
• Polarizability: 39.267475 Å^3
• Polar Surface Area: 172.42 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03AMC031

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

REFERENCES

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