(4S)-4-{[(1S)-1-{[(1S)-2-carboxy-1-[(4-methyl-2-oxo-2H-chromen-7-yl)carbamoyl]ethyl]carbamoyl}-2-(1H-imidazol-4-yl)ethyl]carbamoyl}-4-[(2S)-2-acetamido-3-(1H-indol-3-yl)propanamido]butanoic acid

• ChemBase ID: 106450
• Molecular Formular: C38H40N8O11
• Molecular Mass: 784.7712
• Monoisotopic Mass: 784.28165414
• SMILES: CC(=O)N[C@@H](Cc1c[nH]c2c1cccc2)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](Cc1c[nH]cn1)C(=O)N[C@@H](CC(=O)O)C(=O)Nc1ccc2c(c1)oc(=O)cc2C
• Canonical SMILES: OC(=O)CC[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)Nc1ccc2c(c1)oc(=O)cc2C)CC(=O)O)Cc1c[nH]cn1)NC(=O)[C@H](Cc1c[nH]c2c1cccc2)NC(=O)C
• InChI: InChI=1S/C38H40N8O11/c1-19-11-34(52)57-31-14-22(7-8-24(19)31)43-36(54)30(15-33(50)51)46-38(56)29(13-23-17-39-18-41-23)45-35(53)27(9-10-32(48)49)44-37(55)28(42-20(2)47)12-21-16-40-26-6-4-3-5-25(21)26/h3-8,11,14,16-18,27-30,40H,9-10,12-13,15H2,1-2H3,(H,39,41)(H,42,47)(H,43,54)(H,44,55)(H,45,53)(H,46,56)(H,48,49)(H,50,51)/t27-,28-,29-,30-/m0/s1
• InChIKey: NONBZTYCHSGHGG-KRCBVYEFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-{[(1S)-1-{[(1S)-2-carboxy-1-[(4-methyl-2-oxo-2H-chromen-7-yl)carbamoyl]ethyl]carbamoyl}-2-(1H-imidazol-4-yl)ethyl]carbamoyl}-4-[(2S)-2-acetamido-3-(1H-indol-3-yl)propanamido]butanoic acid
• IUPAC Traditional name: (4S)-4-{[(1S)-1-{[(1S)-2-carboxy-1-[(4-methyl-2-oxochromen-7-yl)carbamoyl]ethyl]carbamoyl}-2-(1H-imidazol-4-yl)ethyl]carbamoyl}-4-[(2S)-2-acetamido-3-(1H-indol-3-yl)propanamido]butanoic acid
• Synonyms: Ac-Trp-Glu-His-Asp-AMC; Ac-WEHD-AMC; Ac-Trp-Glu-His-Asp-7-Amino-4-Methylcoumarin; N-Acetyl-Trp-Glu-His-Asp-7-amido-4-methylcoumarin

Database IDs

• MDL Number: MFCD01318829
• PubChem SID: 162093002
• PubChem CID: 25108637

CALCULATED PROPERTIES

• Acid pKa: 3.426926
• H Acceptors: 11
• H Donor: 9
• LogD (pH = 5.5): -3.2320127
• LogD (pH = 7.4): -5.78794
• Log P: -1.935558
• Molar Refractivity: 199.4105 cm^3
• Polarizability: 77.29002 Å^3
• Polar Surface Area: 290.87 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: white powder

Safety Information

• German water hazard class: 3
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: human ... CASP1(834)mouse ... CASP1(12362)rat ... CASP1(25166)

Product Information

• Purity: ≥97% (HPLC)

DETAILS

MP Biomedicals - 03AMC156

A fluorogenic substrate for detecting caspase-1, caspase-4, and caspase-5 activity.
Excitation max.: 365-380 nm, Emission max.: 430-460 nm

Sigma Aldrich - A0216

Biochem/physiol Actions
Fluorogenic substrate for caspase 1.

REFERENCES

• Thornberry, N.A. et al., J. Biol. Chem., 272:17907 (1997)
• Thornberry, N.A., and Lazebnik, Y. 1998. Science 281, 1312.