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

• ChemBase ID: 106442
• Molecular Formular: C31H41N5O12
• Molecular Mass: 675.68354
• Monoisotopic Mass: 675.27517178
• SMILES: CC[C@H](C)[C@H](NC(=O)C)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H]([C@@H](C)O)C(=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)N[C@H](C(=O)N[C@H](C(=O)Nc1ccc2c(c1)oc(=O)cc2C)CC(=O)O)[C@H](O)C)CCC(=O)O)NC(=O)C)C
• InChI: InChI=1S/C31H41N5O12/c1-6-14(2)26(32-17(5)38)30(46)34-20(9-10-23(39)40)28(44)36-27(16(4)37)31(47)35-21(13-24(41)42)29(45)33-18-7-8-19-15(3)11-25(43)48-22(19)12-18/h7-8,11-12,14,16,20-21,26-27,37H,6,9-10,13H2,1-5H3,(H,32,38)(H,33,45)(H,34,46)(H,35,47)(H,36,44)(H,39,40)(H,41,42)/t14-,16+,20-,21-,26-,27-/m0/s1
• InChIKey: ZYTCBVQZQSFKHQ-HGZCCCDHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-{[(1S,2R)-1-{[(1S)-2-carboxy-1-[(4-methyl-2-oxo-2H-chromen-7-yl)carbamoyl]ethyl]carbamoyl}-2-hydroxypropyl]carbamoyl}-4-[(2S,3S)-2-acetamido-3-methylpentanamido]butanoic acid
• IUPAC Traditional name: (4S)-4-{[(1S,2R)-1-{[(1S)-2-carboxy-1-[(4-methyl-2-oxochromen-7-yl)carbamoyl]ethyl]carbamoyl}-2-hydroxypropyl]carbamoyl}-4-[(2S,3S)-2-acetamido-3-methylpentanamido]butanoic acid
• Synonyms: Ac-Ile-Glu-Thr-Asp-AMC; Ac-IETD-AMC; Ac-Ile-Glu-Thr-Asp-7-Amino-4-Methylcoumarin; N-Acetyl-Ile-Glu-Thr-Asp-7-Amido-4-methylcoumarin

Database IDs

• MDL Number: MFCD01630896
• PubChem SID: 162090102; 24890834
• PubChem CID: 24799009

CALCULATED PROPERTIES

• Acid pKa: 3.5440419
• H Acceptors: 11
• H Donor: 8
• LogD (pH = 5.5): -4.372525
• LogD (pH = 7.4): -7.551069
• Log P: -1.1188451
• Molar Refractivity: 166.2681 cm^3
• Polarizability: 64.22879 Å^3
• Polar Surface Area: 266.63 Å^2
• Rotatable Bonds: 17
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO/DMF: soluble1 mg/mL
• 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 ... 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)

DETAILS

MP Biomedicals - 03AMC140

A fluorogenic substrate for Caspase-8 and Granzyme B.

Sigma Aldrich - A4188

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

REFERENCES

• Thornberry, H.A. et al., Science, 281:1312 (1998).
• Talanian, R.V. et al., J. Biol. Chem., 272:9677 (1997).