benzyl N-{2-[(2S)-2-{[(1S)-4-carbamimidamido-1-{[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]carbamoyl}butyl]carbamoyl}pyrrolidin-1-yl]-2-oxoethyl}carbamate

• ChemBase ID: 106317
• Molecular Formular: C31H34F3N7O7
• Molecular Mass: 673.6395696
• Monoisotopic Mass: 673.24718112
• SMILES: NC(=N)NCCC[C@H](NC(=O)[C@@H]1CCCN1C(=O)CNC(=O)OCc1ccccc1)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]1CCCN1C(=O)CNC(=O)OCc1ccccc1
• InChI: InChI=1S/C31H34F3N7O7/c32-31(33,34)21-15-26(43)48-24-14-19(10-11-20(21)24)39-27(44)22(8-4-12-37-29(35)36)40-28(45)23-9-5-13-41(23)25(42)16-38-30(46)47-17-18-6-2-1-3-7-18/h1-3,6-7,10-11,14-15,22-23H,4-5,8-9,12-13,16-17H2,(H,38,46)(H,39,44)(H,40,45)(H4,35,36,37)/t22-,23-/m0/s1
• InChIKey: YNFWCRXESGJYDC-GOTSBHOMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: benzyl N-{2-[(2S)-2-{[(1S)-4-carbamimidamido-1-{[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]carbamoyl}butyl]carbamoyl}pyrrolidin-1-yl]-2-oxoethyl}carbamate
• IUPAC Traditional name: benzyl N-{2-[(2S)-2-{[(1S)-4-carbamimidamido-1-{[2-oxo-4-(trifluoromethyl)chromen-7-yl]carbamoyl}butyl]carbamoyl}pyrrolidin-1-yl]-2-oxoethyl}carbamate
• Synonyms: Z-GRP-AFC trifluoroacetate salt; Z-Gly-Pro-Arg 7-amido-4-trifluoromethylcoumarin trifluoroacetate salt; Z-Gly-Pro-Arg-AFC; Z-GPR-AFC; Z-Gly-Pro-Arg-7-Amino-4-trifluoromethylcoumarin

Database IDs

• MDL Number: MFCD03452879
• PubChem SID: 162105945
• PubChem CID: 25108537

CALCULATED PROPERTIES

• Acid pKa: 11.429934
• H Acceptors: 8
• H Donor: 6
• LogD (pH = 5.5): -1.202608
• LogD (pH = 7.4): -1.1955465
• Log P: 0.73678815
• Molar Refractivity: 176.3755 cm^3
• Polarizability: 62.01844 Å^3
• Polar Surface Area: 205.04 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO or DMF: soluble20 mM
• Apperance: white powder

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: human ... GZMA(3001)mouse ... GZMA(14938)rat ... GZMA(266708)

Product Information

• Purity: ≥97% (HPLC)
• Empirical Formula (Hill Notation): C33H35F6N7O9

DETAILS

MP Biomedicals - 03AFC061

A fluorogenic substrate for Granzyme A.

Sigma Aldrich - C0980

Amino Acid Sequence
Z-Gly-Pro-Arg-AFC
Application
Fluorogenic substrate for granzyme A.

REFERENCES

• Smyth, M.J. et al., J. Biol. Chem., 267(34):24418 (1992).
• Velotti, F. et al., Eur. J. Imm., 22:1049 (1992).