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

• ChemBase ID: 106447
• Molecular Formular: C32H41N5O11
• Molecular Mass: 671.69484
• Monoisotopic Mass: 671.28025716
• 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
• 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)CC(=O)O)CCC(=O)O)NC(=O)C)C
• InChI: InChI=1S/C32H41N5O11/c1-5-16(2)28(33-18(4)38)31(46)35-21(10-11-25(39)40)32(47)37-12-6-7-23(37)30(45)36-22(15-26(41)42)29(44)34-19-8-9-20-17(3)13-27(43)48-24(20)14-19/h8-9,13-14,16,21-23,28H,5-7,10-12,15H2,1-4H3,(H,33,38)(H,34,44)(H,35,46)(H,36,45)(H,39,40)(H,41,42)/t16-,21-,22-,23-,28-/m0/s1
• InChIKey: XDMHHBKPMUGLEA-MNTOYCOOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-5-[(2S)-2-{[(1S)-2-carboxy-1-[(4-methyl-2-oxo-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-[(4-methyl-2-oxochromen-7-yl)carbamoyl]ethyl]carbamoyl}pyrrolidin-1-yl]-4-[(2S,3S)-2-acetamido-3-methylpentanamido]-5-oxopentanoic acid
• Synonyms: Ac-Ile-Glu-Pro-Asp-AMC; Ac-IEPD-AMC; Ac-Ile-Glu-Pro-Asp-7-Amino-4-Methylcoumarin; N-Acetyl-Ile-Glu-Pro-Asp-7-amido-4-methylcoumarin

Database IDs

• MDL Number: MFCD02259622
• PubChem SID: 162088306
• PubChem CID: 25108634

CALCULATED PROPERTIES

• Acid pKa: 3.5830705
• H Acceptors: 10
• H Donor: 6
• LogD (pH = 5.5): -3.3933961
• LogD (pH = 7.4): -6.606945
• Log P: -0.21584456
• Molar Refractivity: 167.9947 cm^3
• Polarizability: 64.66461 Å^3
• Polar Surface Area: 237.61 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO/DMF: soluble1 mg/mL
• Apperance: 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 ... CARD8(22900), CASP8(841), CASP8AP2(9994), CFLAR(8837), GZMB(3002)mouse ... CFLAR(117279), GZMB(171528)rat ... CASP8(12370), CFLAR(12633), GZMB(14939), RGD1561819(502004), RGD1562700(502007)

Product Information

• Purity: ≥97% (HPLC)
• Shipped in: dry ice

DETAILS

MP Biomedicals - 03AMC153

A fluorogenic substrate for Granzyme B (kcat/Km = 3,330 M^-1s^-1) that also recognizes granzyme B variants (kcat/Km = 55 M^-1s^-1 for R192A and kcat/Km = 8.8 M^-1s^-1 for R192E).
Excitation max.: 360 - 380 nm, Emission max.: 430 - 460 nm

Sigma Aldrich - A6220

Amino Acid Sequence
NAc-Ile-Glu-Pro-Asp-AMC
Substrates
Fluorogenic substrate for caspase 8 and granzyme B.

REFERENCES

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