methyl 3-{[(1S)-1-{[(2S)-1-[(2S)-2-{[(1S)-3-(methylsulfanyl)-1-{[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]carbamoyl}propyl]carbamoyl}pyrrolidin-1-yl]-1-oxopropan-2-yl]carbamoyl}ethyl]carbamoyl}propanoate

• ChemBase ID: 106333
• Molecular Formular: C31H38F3N5O9S
• Molecular Mass: 713.7217296
• Monoisotopic Mass: 713.23423348
• SMILES: COC(=O)CCC(=O)N[C@@H](C)C(=O)N[C@@H](C)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CCSC)C(=O)Nc1ccc2c(c1)oc(=O)cc2C(F)(F)F
• Canonical SMILES: CSCC[C@@H](C(=O)Nc1ccc2c(c1)oc(=O)cc2C(F)(F)F)NC(=O)[C@@H]1CCCN1C(=O)[C@@H](NC(=O)[C@@H](NC(=O)CCC(=O)OC)C)C
• InChI: InChI=1S/C31H38F3N5O9S/c1-16(35-24(40)9-10-25(41)47-3)27(43)36-17(2)30(46)39-12-5-6-22(39)29(45)38-21(11-13-49-4)28(44)37-18-7-8-19-20(31(32,33)34)15-26(42)48-23(19)14-18/h7-8,14-17,21-22H,5-6,9-13H2,1-4H3,(H,35,40)(H,36,43)(H,37,44)(H,38,45)/t16-,17-,21-,22-/m0/s1
• InChIKey: NRPSMRULMMCPBR-FHQLIMNDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl 3-{[(1S)-1-{[(2S)-1-[(2S)-2-{[(1S)-3-(methylsulfanyl)-1-{[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]carbamoyl}propyl]carbamoyl}pyrrolidin-1-yl]-1-oxopropan-2-yl]carbamoyl}ethyl]carbamoyl}propanoate
• IUPAC Traditional name: methyl 3-{[(1S)-1-{[(2S)-1-[(2S)-2-{[(1S)-3-(methylsulfanyl)-1-{[2-oxo-4-(trifluoromethyl)chromen-7-yl]carbamoyl}propyl]carbamoyl}pyrrolidin-1-yl]-1-oxopropan-2-yl]carbamoyl}ethyl]carbamoyl}propanoate
• Synonyms: MeOSuc-Ala-Ala-Pro-Met-AFC; MeOSuc-AAPM-AFC; MeOSuc-Ala-Ala-Pro-Met-7-Amino-4-trifluoromethylcoumarin

Database IDs

• PubChem SID: 162105400
• PubChem CID: 25108553

CALCULATED PROPERTIES

• Acid pKa: 11.5403595
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): 0.43366608
• LogD (pH = 7.4): 0.43363848
• Log P: 0.43366644
• Molar Refractivity: 171.2559 cm^3
• Polarizability: 64.93108 Å^3
• Polar Surface Area: 189.31 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03AFC096

A fluorogenic substrate for Human Pancreatic 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).