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

• ChemBase ID: 106451
• Molecular Formular: C37H45N5O9
• Molecular Mass: 703.7813
• Monoisotopic Mass: 703.32172805
• SMILES: CC(C)C[C@H](NC(=O)[C@H](C)NC(=O)CCC(=O)O)C(=O)N1CCC[C@H]1C(=O)N[C@@H](Cc1ccccc1)C(=O)Nc1ccc2c(c1)oc(=O)cc2C
• Canonical SMILES: CC(C[C@@H](C(=O)N1CCC[C@H]1C(=O)N[C@H](C(=O)Nc1ccc2c(c1)oc(=O)cc2C)Cc1ccccc1)NC(=O)[C@@H](NC(=O)CCC(=O)O)C)C
• InChI: InChI=1S/C37H45N5O9/c1-21(2)17-28(41-34(47)23(4)38-31(43)14-15-32(44)45)37(50)42-16-8-11-29(42)36(49)40-27(19-24-9-6-5-7-10-24)35(48)39-25-12-13-26-22(3)18-33(46)51-30(26)20-25/h5-7,9-10,12-13,18,20-21,23,27-29H,8,11,14-17,19H2,1-4H3,(H,38,43)(H,39,48)(H,40,49)(H,41,47)(H,44,45)/t23-,27-,28-,29-/m0/s1
• InChIKey: SNPHBYYALNEWEY-HPEBZSCQSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• PubChem SID: 162105497
• PubChem CID: 25108639

CALCULATED PROPERTIES

• Acid pKa: 4.0904903
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): 0.75953156
• LogD (pH = 7.4): -0.9225523
• Log P: 2.1823535
• Molar Refractivity: 186.7582 cm^3
• Polarizability: 71.72345 Å^3
• Polar Surface Area: 200.31 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03AMC163

A fluorogenic PPIases (peptidyl-Prolyl cis-trans Isomerase) substrate.

REFERENCES

• Kofron, J.L. et al., Biochem., 30:6127 (1991).