3-{[(1S)-1-{[(2S)-1-[(2S)-2-{[(1S)-1-[(4-methyl-2-oxo-2H-chromen-7-yl)carbamoyl]ethyl]carbamoyl}pyrrolidin-1-yl]-1-oxopropan-2-yl]carbamoyl}ethyl]carbamoyl}propanoic acid

• ChemBase ID: 106427
• Molecular Formular: C28H35N5O9
• Molecular Mass: 585.6056
• Monoisotopic Mass: 585.24347773
• SMILES: C[C@H](NC(=O)CCC(=O)O)C(=O)N[C@@H](C)C(=O)N1CCC[C@H]1C(=O)N[C@@H](C)C(=O)Nc1ccc2c(c1)oc(=O)cc2C
• Canonical SMILES: O=C(N[C@H](C(=O)N[C@H](C(=O)N1CCC[C@H]1C(=O)N[C@H](C(=O)Nc1ccc2c(c1)oc(=O)cc2C)C)C)C)CCC(=O)O
• InChI: InChI=1S/C28H35N5O9/c1-14-12-24(37)42-21-13-18(7-8-19(14)21)32-26(39)16(3)30-27(40)20-6-5-11-33(20)28(41)17(4)31-25(38)15(2)29-22(34)9-10-23(35)36/h7-8,12-13,15-17,20H,5-6,9-11H2,1-4H3,(H,29,34)(H,30,40)(H,31,38)(H,32,39)(H,35,36)/t15-,16-,17-,20-/m0/s1
• InChIKey: FSNMGMXQJSGLJK-BOSXTWCSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-{[(1S)-1-{[(2S)-1-[(2S)-2-{[(1S)-1-[(4-methyl-2-oxo-2H-chromen-7-yl)carbamoyl]ethyl]carbamoyl}pyrrolidin-1-yl]-1-oxopropan-2-yl]carbamoyl}ethyl]carbamoyl}propanoic acid
• IUPAC Traditional name: 3-{[(1S)-1-{[(2S)-1-[(2S)-2-{[(1S)-1-[(4-methyl-2-oxochromen-7-yl)carbamoyl]ethyl]carbamoyl}pyrrolidin-1-yl]-1-oxopropan-2-yl]carbamoyl}ethyl]carbamoyl}propanoic acid
• Synonyms: Suc-Ala-Ala-Pro-Ala-AMC; Suc-AAPA-AMC; Suc-Ala-Ala-Pro-Ala-7-Amino-4-Methylcoumarin

Database IDs

• PubChem SID: 162105452
• PubChem CID: 25108617

CALCULATED PROPERTIES

• Acid pKa: 4.0904903
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -2.150905
• LogD (pH = 7.4): -3.8329904
• Log P: -0.7280831
• Molar Refractivity: 148.4656 cm^3
• Polarizability: 56.72322 Å^3
• Polar Surface Area: 200.31 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03AMC092

A fluorogenic substrate for Leukocyte Elastase.

REFERENCES

• Stein, R. L. et al., Biochem., 25:5414 (1986).
• Del Mar, E.G. et al., Biochem., 19:468 (1980).
• Castillo, M.J. et al., Anal. Biochem., 99:53 (1979).