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

• ChemBase ID: 106345
• Molecular Formular: C29H39F3N8O8
• Molecular Mass: 684.6639696
• Monoisotopic Mass: 684.28429491
• SMILES: C[C@H](NC(=O)[C@H](CCC(=O)N)NC(=O)OC(C)(C)C)C(=O)N[C@@H](CCCNC(=N)N)C(=O)Nc1ccc2c(c1)oc(=O)cc2C(F)(F)F
• Canonical SMILES: NC(=N)NCCC[C@@H](C(=O)Nc1ccc2c(c1)oc(=O)cc2C(F)(F)F)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)OC(C)(C)C)CCC(=O)N)C
• InChI: InChI=1S/C29H39F3N8O8/c1-14(37-24(44)19(9-10-21(33)41)40-27(46)48-28(2,3)4)23(43)39-18(6-5-11-36-26(34)35)25(45)38-15-7-8-16-17(29(30,31)32)13-22(42)47-20(16)12-15/h7-8,12-14,18-19H,5-6,9-11H2,1-4H3,(H2,33,41)(H,37,44)(H,38,45)(H,39,43)(H,40,46)(H4,34,35,36)/t14-,18-,19-/m0/s1
• InChIKey: ALXQQQQMEFASQB-JVPBZIDWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tert-butyl N-[(1S)-1-{[(1S)-1-{[(1S)-4-carbamimidamido-1-{[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]carbamoyl}butyl]carbamoyl}ethyl]carbamoyl}-3-carbamoylpropyl]carbamate
• IUPAC Traditional name: tert-butyl N-[(1S)-1-{[(1S)-1-{[(1S)-4-carbamimidamido-1-{[2-oxo-4-(trifluoromethyl)chromen-7-yl]carbamoyl}butyl]carbamoyl}ethyl]carbamoyl}-3-carbamoylpropyl]carbamate
• Synonyms: Boc-Gln-Ala-Arg-AFC; Boc-QAR-AFC; Boc-Gln-Ala-Arg-7-Amino-4-trifluoromethylcoumarin

Database IDs

• PubChem SID: 162105491
• PubChem CID: 25108565

CALCULATED PROPERTIES

• Acid pKa: 11.360868
• H Acceptors: 9
• H Donor: 8
• LogD (pH = 5.5): -2.7371056
• LogD (pH = 7.4): -2.7292182
• Log P: -0.8597135
• Molar Refractivity: 174.9859 cm^3
• Polarizability: 61.880646 Å^3
• Polar Surface Area: 256.92 Å^2
• Rotatable Bonds: 17
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03AFC123

A fluorogenic substrate for Trypsin.

REFERENCES

• Kawabata, S. et al., Eur. J. Biochem., 172:17 (1988).