(4S)-5-[(2S)-2-{[(1S)-2-carboxy-1-{[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]carbamoyl}ethyl]carbamoyl}pyrrolidin-1-yl]-4-[(2S,3S)-2-acetamido-3-methylpentanamido]-5-oxopentanoic acid

• ChemBase ID: 106356
• Molecular Formular: C32H38F3N5O11
• Molecular Mass: 725.6662296
• Monoisotopic Mass: 725.25199172
• SMILES: CC[C@H](C)[C@H](NC(=O)C)C(=O)N[C@@H](CCC(=O)O)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CC(=O)O)C(=O)Nc1ccc2c(c1)oc(=O)cc2C(F)(F)F
• Canonical SMILES: CC[C@@H]([C@@H](C(=O)N[C@H](C(=O)N1CCC[C@H]1C(=O)N[C@H](C(=O)Nc1ccc2c(c1)oc(=O)cc2C(F)(F)F)CC(=O)O)CCC(=O)O)NC(=O)C)C
• InChI: InChI=1S/C32H38F3N5O11/c1-4-15(2)27(36-16(3)41)30(49)38-20(9-10-24(42)43)31(50)40-11-5-6-22(40)29(48)39-21(14-25(44)45)28(47)37-17-7-8-18-19(32(33,34)35)13-26(46)51-23(18)12-17/h7-8,12-13,15,20-22,27H,4-6,9-11,14H2,1-3H3,(H,36,41)(H,37,47)(H,38,49)(H,39,48)(H,42,43)(H,44,45)/t15-,20-,21-,22-,27-/m0/s1
• InChIKey: HWXKKVLJPWMVLL-FGGUPADCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-5-[(2S)-2-{[(1S)-2-carboxy-1-{[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]carbamoyl}ethyl]carbamoyl}pyrrolidin-1-yl]-4-[(2S,3S)-2-acetamido-3-methylpentanamido]-5-oxopentanoic acid
• IUPAC Traditional name: (4S)-5-[(2S)-2-{[(1S)-2-carboxy-1-{[2-oxo-4-(trifluoromethyl)chromen-7-yl]carbamoyl}ethyl]carbamoyl}pyrrolidin-1-yl]-4-[(2S,3S)-2-acetamido-3-methylpentanamido]-5-oxopentanoic acid
• Synonyms: N-Acetyl-Ile-Glu-Pro-Asp-7-amino-4-trifluoromethylcoumarin; Ac-Ile-Glu-Pro-Asp-AFC; Ac-IEPD-AFC; Ac-Ile-Glu-Pro-Asp-7-Amino-4-trifluoromethylcoumarin

Database IDs

• MDL Number: MFCD03452821
• PubChem SID: 162105412
• PubChem CID: 25108575

CALCULATED PROPERTIES

• Acid pKa: 3.5597808
• H Acceptors: 10
• H Donor: 6
• LogD (pH = 5.5): -3.061189
• LogD (pH = 7.4): -6.2564764
• Log P: 0.14858253
• Molar Refractivity: 168.9272 cm^3
• Polarizability: 64.15622 Å^3
• Polar Surface Area: 237.61 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO/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 ... GZMB(3002)mouse ... GZMB(171528)rat ... GZMB(14939), RGD1561819(502004), RGD1562700(502007)

Product Information

• Purity: 97% (HPLC)
• Shipped in: dry ice
• Linear Formula: C32H38N5O11F3

DETAILS

MP Biomedicals - 03AFC153

A fluorogenic substrate for Granzyme B.

Sigma Aldrich - A6345

Amino Acid Sequence
NAc-Ile-Glu-Pro-Asp-AFC
Application
Fluorogenic substrate for granzyme B.

REFERENCES

• Harris, J.L. et al., J. Biol. Chem., 273:27364 (1998).
• Thornberry, N.A. et al., Science, 281:1312 (1998).