(2S)-6-amino-2-[(2S)-2-[(2S)-2-acetamidopropanamido]propanamido]-N-[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]hexanamide

• ChemBase ID: 106305
• Molecular Formular: C24H30F3N5O6
• Molecular Mass: 541.5201096
• Monoisotopic Mass: 541.21481837
• SMILES: C[C@H](NC(=O)C)C(=O)N[C@@H](C)C(=O)N[C@@H](CCCCN)C(=O)Nc1ccc2c(c1)oc(=O)cc2C(F)(F)F
• Canonical SMILES: NCCCC[C@@H](C(=O)Nc1ccc2c(c1)oc(=O)cc2C(F)(F)F)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)C)C)C
• InChI: InChI=1S/C24H30F3N5O6/c1-12(29-14(3)33)21(35)30-13(2)22(36)32-18(6-4-5-9-28)23(37)31-15-7-8-16-17(24(25,26)27)11-20(34)38-19(16)10-15/h7-8,10-13,18H,4-6,9,28H2,1-3H3,(H,29,33)(H,30,35)(H,31,37)(H,32,36)/t12-,13-,18-/m0/s1
• InChIKey: XSSJBUKTAFWLLP-LXIYXOSZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-6-amino-2-[(2S)-2-[(2S)-2-acetamidopropanamido]propanamido]-N-[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]hexanamide
• IUPAC Traditional name: (2S)-6-amino-2-[(2S)-2-[(2S)-2-acetamidopropanamido]propanamido]-N-[2-oxo-4-(trifluoromethyl)chromen-7-yl]hexanamide
• Synonyms: Ac-Ala-Ala-Lys-AFC; Ac-AAK-AFC; Ac-Ala-Ala-Lys-7-Amino-4-trifluoromethylcoumarin

Database IDs

• PubChem SID: 162105942
• PubChem CID: 25108526

CALCULATED PROPERTIES

• Acid pKa: 11.561179
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): -3.0804808
• LogD (pH = 7.4): -2.6585913
• Log P: -0.22344543
• Molar Refractivity: 130.8305 cm^3
• Polarizability: 49.145344 Å^3
• Polar Surface Area: 168.72 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03AFC048

A fluorogenic substrate for Tryptase.

REFERENCES

• Schwartz, L.B. et al., The N. E. J. of Med., June 25 (1987).
• Schwartz, L.B. et al., J. Imm., 126:1290 (1981).