(4S)-4-{[(1S)-1-{[(1S)-2-carboxy-1-[(4-methyl-2-oxo-2H-chromen-7-yl)carbamoyl]ethyl]carbamoyl}-2-methylpropyl]carbamoyl}-4-[(2S)-3-carboxy-2-acetamidopropanamido]butanoic acid

• ChemBase ID: 106441
• Molecular Formular: C30H37N5O13
• Molecular Mass: 675.64048
• Monoisotopic Mass: 675.23878627
• SMILES: CC(C)[C@H](NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CC(=O)O)NC(=O)C)C(=O)N[C@@H](CC(=O)O)C(=O)Nc1ccc2c(c1)oc(=O)cc2C
• Canonical SMILES: OC(=O)C[C@@H](C(=O)Nc1ccc2c(c1)oc(=O)cc2C)NC(=O)[C@H](C(C)C)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)C)CC(=O)O)CCC(=O)O
• InChI: InChI=1S/C30H37N5O13/c1-13(2)26(35-27(44)18(7-8-22(37)38)33-29(46)19(11-23(39)40)31-15(4)36)30(47)34-20(12-24(41)42)28(45)32-16-5-6-17-14(3)9-25(43)48-21(17)10-16/h5-6,9-10,13,18-20,26H,7-8,11-12H2,1-4H3,(H,31,36)(H,32,45)(H,33,46)(H,34,47)(H,35,44)(H,37,38)(H,39,40)(H,41,42)/t18-,19-,20-,26-/m0/s1
• InChIKey: ALZSTTDFHZHSCA-RNVDEAKXSA-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-methylpropyl]carbamoyl}-4-[(2S)-3-carboxy-2-acetamidopropanamido]butanoic acid
• IUPAC Traditional name: (4S)-4-{[(1S)-1-{[(1S)-2-carboxy-1-[(4-methyl-2-oxochromen-7-yl)carbamoyl]ethyl]carbamoyl}-2-methylpropyl]carbamoyl}-4-[(2S)-3-carboxy-2-acetamidopropanamido]butanoic acid
• Synonyms: Ac-Asp-Glu-Val-Asp-AMC; Ac-DEVD-AMC; Ac-Asp-Glu-Val-Asp-7-Amino-4-Methylcoumarin

Database IDs

• CAS Number: 169332-61-0
• PubChem SID: 162087694
• PubChem CID: 9896164

CALCULATED PROPERTIES

• Acid pKa: 3.3991728
• H Acceptors: 12
• H Donor: 8
• LogD (pH = 5.5): -6.3623433
• LogD (pH = 7.4): -11.170207
• Log P: -1.5748907
• Molar Refractivity: 161.74 cm^3
• Polarizability: 62.393684 Å^3
• Polar Surface Area: 283.7 Å^2
• Rotatable Bonds: 17
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03AMC138

A fluorogenic substrate for Caspase-3 (CPP32, YAMA). Cleavage of this substrate by caspase-3 shows Michaelis-Menten kinetics (Km = 9.7 ± 1.0 μM). Also a substrate for caspase-6, caspase-7, caspase-8, and caspase-10.
Excitation max.: 365-380 nm, Emission max.: 430-460 nm

REFERENCES

• Thornberry, N.A. et al., Science, 281:1312 (1998).
• Nicholson, D.W. et al., Nature, 376:37 (1995).
• Hermission, M., et al. 2000. Oncogene 19, 2338.