(2S)-2-[(2S)-2-amino-3-hydroxypropanamido]-3-(4-hydroxyphenyl)-N-(4-methyl-2-oxo-2H-chromen-7-yl)propanamide

• ChemBase ID: 106403
• Molecular Formular: C22H23N3O6
• Molecular Mass: 425.43452
• Monoisotopic Mass: 425.15868547
• SMILES: Cc1cc(=O)oc2c1ccc(NC(=O)[C@H](Cc1ccc(cc1)O)NC(=O)[C@@H](N)CO)c2
• Canonical SMILES: OC[C@@H](C(=O)N[C@H](C(=O)Nc1ccc2c(c1)oc(=O)cc2C)Cc1ccc(cc1)O)N
• InChI: InChI=1S/C22H23N3O6/c1-12-8-20(28)31-19-10-14(4-7-16(12)19)24-22(30)18(25-21(29)17(23)11-26)9-13-2-5-15(27)6-3-13/h2-8,10,17-18,26-27H,9,11,23H2,1H3,(H,24,30)(H,25,29)/t17-,18-/m0/s1
• InChIKey: IZBGRBDFCWTGBH-ROUUACIJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(2S)-2-amino-3-hydroxypropanamido]-3-(4-hydroxyphenyl)-N-(4-methyl-2-oxo-2H-chromen-7-yl)propanamide
• IUPAC Traditional name: (2S)-2-[(2S)-2-amino-3-hydroxypropanamido]-3-(4-hydroxyphenyl)-N-(4-methyl-2-oxochromen-7-yl)propanamide
• Synonyms: Ser-Tyr-AMC; SY-AMC; Ser-Tyr-7-Amino-4-Methylcoumarin

Database IDs

• PubChem SID: 162105574
• PubChem CID: 24802512

CALCULATED PROPERTIES

• Acid pKa: 9.506954
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): -1.2746508
• LogD (pH = 7.4): 0.350532
• Log P: 0.6017832
• Molar Refractivity: 113.9882 cm^3
• Polarizability: 43.382504 Å^3
• Polar Surface Area: 150.98 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

DETAILS

MP Biomedicals - 03AMC041

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

REFERENCES

• McGuire, J.M. et al., J. Biol. Chem., 268(4):2458 (1993).