(2S)-2-(2-aminoacetamido)-N-(4-methyl-2-oxo-2H-chromen-7-yl)-3-phenylpropanamide

• ChemBase ID: 106397
• Molecular Formular: C21H21N3O4
• Molecular Mass: 379.40914
• Monoisotopic Mass: 379.15320617
• SMILES: Cc1cc(=O)oc2c1ccc(NC(=O)[C@H](Cc1ccccc1)NC(=O)CN)c2
• Canonical SMILES: NCC(=O)N[C@H](C(=O)Nc1ccc2c(c1)oc(=O)cc2C)Cc1ccccc1
• InChI: InChI=1S/C21H21N3O4/c1-13-9-20(26)28-18-11-15(7-8-16(13)18)23-21(27)17(24-19(25)12-22)10-14-5-3-2-4-6-14/h2-9,11,17H,10,12,22H2,1H3,(H,23,27)(H,24,25)/t17-/m0/s1
• InChIKey: OXYDLMUFQZNZMD-KRWDZBQOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-(2-aminoacetamido)-N-(4-methyl-2-oxo-2H-chromen-7-yl)-3-phenylpropanamide
• IUPAC Traditional name: (2S)-2-(2-aminoacetamido)-N-(4-methyl-2-oxochromen-7-yl)-3-phenylpropanamide
• Synonyms: Gly-Phe-AMC; GF-AMC; Gly-Phe-7-Amino-4-Methylcoumarin

Database IDs

• PubChem SID: 162105436
• PubChem CID: 7015854

CALCULATED PROPERTIES

• Acid pKa: 12.101134
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -0.7445705
• LogD (pH = 7.4): 0.9436842
• Log P: 1.5161421
• Molar Refractivity: 105.9697 cm^3
• Polarizability: 40.277176 Å^3
• Polar Surface Area: 110.52 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

MP Biomedicals - 03AMC033

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

REFERENCES

• Smith, M.J. et al., J. Imm., 154:6299 (1995).