(4S)-4-[(2S)-2-{[(tert-butoxy)carbonyl]amino}-4-carbamoylbutanamido]-4-{[(1S)-4-carbamimidamido-1-{[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]carbamoyl}butyl]carbamoyl}butanoic acid

• ChemBase ID: 106348
• Molecular Formular: C31H41F3N8O10
• Molecular Mass: 742.7000496
• Monoisotopic Mass: 742.28977421
• SMILES: CC(C)(C)OC(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H](CCC(=O)O)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)CCC(=O)O
• InChI: InChI=1S/C31H41F3N8O10/c1-30(2,3)52-29(50)42-20(8-10-22(35)43)27(49)41-19(9-11-23(44)45)26(48)40-18(5-4-12-38-28(36)37)25(47)39-15-6-7-16-17(31(32,33)34)14-24(46)51-21(16)13-15/h6-7,13-14,18-20H,4-5,8-12H2,1-3H3,(H2,35,43)(H,39,47)(H,40,48)(H,41,49)(H,42,50)(H,44,45)(H4,36,37,38)/t18-,19-,20-/m0/s1
• InChIKey: DQWXQNDNBGRMQX-UFYCRDLUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-[(2S)-2-{[(tert-butoxy)carbonyl]amino}-4-carbamoylbutanamido]-4-{[(1S)-4-carbamimidamido-1-{[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]carbamoyl}butyl]carbamoyl}butanoic acid
• IUPAC Traditional name: (4S)-4-[(2S)-2-[(tert-butoxycarbonyl)amino]-4-carbamoylbutanamido]-4-{[(1S)-4-carbamimidamido-1-{[2-oxo-4-(trifluoromethyl)chromen-7-yl]carbamoyl}butyl]carbamoyl}butanoic acid
• Synonyms: Boc-Gln-Gly-Arg-AFC; Boc-QGR-AFC; Boc-Gln-Gly-Arg-7-Amino-4-trifluoromethylcoumarin

Database IDs

• PubChem SID: 162105573
• PubChem CID: 25108568

CALCULATED PROPERTIES

• Acid pKa: 3.6594782
• H Acceptors: 11
• H Donor: 9
• LogD (pH = 5.5): -2.3249884
• LogD (pH = 7.4): -2.3199348
• Log P: -2.3200188
• Molar Refractivity: 185.7763 cm^3
• Polarizability: 66.205864 Å^3
• Polar Surface Area: 294.22 Å^2
• Rotatable Bonds: 20
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03AFC137

A fluorogenic substrate for Factor XIIa.

REFERENCES

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