tert-butyl N-[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-4-carbamimidamido-1-{[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]carbamoyl}butyl]carbamoyl}-2-hydroxyethyl]carbamoyl}-2-phenylethyl]carbamoyl}-3-methylbutyl]carbamate

• ChemBase ID: 106323
• Molecular Formular: C39H51F3N8O9
• Molecular Mass: 832.8656496
• Monoisotopic Mass: 832.37310991
• SMILES: CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCNC(=N)N)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)CCCNC(=N)N)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)OC(C)(C)C)CC(C)C)Cc1ccccc1
• InChI: InChI=1S/C39H51F3N8O9/c1-21(2)16-27(50-37(57)59-38(3,4)5)33(54)48-28(17-22-10-7-6-8-11-22)34(55)49-29(20-51)35(56)47-26(12-9-15-45-36(43)44)32(53)46-23-13-14-24-25(39(40,41)42)19-31(52)58-30(24)18-23/h6-8,10-11,13-14,18-19,21,26-29,51H,9,12,15-17,20H2,1-5H3,(H,46,53)(H,47,56)(H,48,54)(H,49,55)(H,50,57)(H4,43,44,45)/t26-,27-,28-,29-/m0/s1
• InChIKey: VYTHQVWYPJJNMZ-DZUOILHNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tert-butyl N-[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-4-carbamimidamido-1-{[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]carbamoyl}butyl]carbamoyl}-2-hydroxyethyl]carbamoyl}-2-phenylethyl]carbamoyl}-3-methylbutyl]carbamate
• IUPAC Traditional name: tert-butyl N-[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-4-carbamimidamido-1-{[2-oxo-4-(trifluoromethyl)chromen-7-yl]carbamoyl}butyl]carbamoyl}-2-hydroxyethyl]carbamoyl}-2-phenylethyl]carbamoyl}-3-methylbutyl]carbamate
• Synonyms: Boc-Leu-Phe-Ser-Arg-AFC; Boc-LFSR-AFC; Boc-Leu-Phe-Ser-Arg-7-Amino-4-trifluoromethylcoumarin

Database IDs

• PubChem SID: 162105395
• PubChem CID: 25108543

CALCULATED PROPERTIES

• Acid pKa: 11.275247
• H Acceptors: 10
• H Donor: 9
• LogD (pH = 5.5): -0.24998437
• LogD (pH = 7.4): -0.24054949
• Log P: 1.5048447
• Molar Refractivity: 219.507 cm^3
• Polarizability: 79.28436 Å^3
• Polar Surface Area: 263.16 Å^2
• Rotatable Bonds: 21
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03AFC075

A fluorogenic substrate for Factor XIa.

REFERENCES

• Reidlinger, T. et al., J. Biol. Chem., 272(40):24899 (1997).