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

• ChemBase ID: 106298
• Molecular Formular: C22H20F3N3O6
• Molecular Mass: 479.4059096
• Monoisotopic Mass: 479.13042004
• SMILES: N[C@@H](CO)C(=O)N[C@@H](Cc1ccc(cc1)O)C(=O)Nc1ccc2c(c1)oc(=O)cc2C(F)(F)F
• Canonical SMILES: OC[C@@H](C(=O)N[C@H](C(=O)Nc1ccc2c(c1)oc(=O)cc2C(F)(F)F)Cc1ccc(cc1)O)N
• InChI: InChI=1S/C22H20F3N3O6/c23-22(24,25)15-9-19(31)34-18-8-12(3-6-14(15)18)27-21(33)17(28-20(32)16(26)10-29)7-11-1-4-13(30)5-2-11/h1-6,8-9,16-17,29-30H,7,10,26H2,(H,27,33)(H,28,32)/t16-,17-/m0/s1
• InChIKey: JZCINVLGEJHLLS-IRXDYDNUSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• PubChem SID: 162105938
• PubChem CID: 25108519

CALCULATED PROPERTIES

• Acid pKa: 9.5025
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): -0.91020584
• LogD (pH = 7.4): 0.71490306
• Log P: 0.964978
• Molar Refractivity: 114.9207 cm^3
• Polarizability: 42.771416 Å^3
• Polar Surface Area: 150.98 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

DETAILS

MP Biomedicals - 03AFC041

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