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

• ChemBase ID: 106446
• Molecular Formular: C29H37N5O11
• Molecular Mass: 631.63098
• Monoisotopic Mass: 631.24895703
• SMILES: CC(C)[C@H](NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](C)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)C)CCC(=O)O
• InChI: InChI=1S/C29H37N5O11/c1-13(2)25(34-27(42)19(8-9-22(36)37)32-26(41)15(4)30-16(5)35)29(44)33-20(12-23(38)39)28(43)31-17-6-7-18-14(3)10-24(40)45-21(18)11-17/h6-7,10-11,13,15,19-20,25H,8-9,12H2,1-5H3,(H,30,35)(H,31,43)(H,32,41)(H,33,44)(H,34,42)(H,36,37)(H,38,39)/t15-,19-,20-,25-/m0/s1
• InChIKey: HBOMYMRWQPWWHL-OHGMFUDRSA-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)-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)-2-acetamidopropanamido]butanoic acid
• Synonyms: Ac-Ala-Glu-Val-Asp-AMC; Ac-AEVD-AMC; Ac-Ala-Glu-Val-Asp-7-Amino-4-Methylcoumarin

Database IDs

• PubChem SID: 162105460
• PubChem CID: 25108633

CALCULATED PROPERTIES

• Acid pKa: 3.6493373
• H Acceptors: 10
• H Donor: 7
• LogD (pH = 5.5): -3.992349
• LogD (pH = 7.4): -7.259782
• Log P: -0.93307877
• Molar Refractivity: 155.7046 cm^3
• Polarizability: 59.904007 Å^3
• Polar Surface Area: 246.4 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03AMC145

A fluorogenic substrate for Caspase-6 and 8.

REFERENCES

• Garcia-Calvo, M. et al., J. Biol. Chem., 273(49):32608 (1998).