(3S)-3-{[(1S)-1-{[(1S)-3-carbamoyl-1-{[(1S)-2-carboxy-1-[(4-methyl-2-oxo-2H-chromen-7-yl)carbamoyl]ethyl]carbamoyl}propyl]carbamoyl}-3-(methylsulfanyl)propyl]carbamoyl}-3-acetamidopropanoic acid

• ChemBase ID: 106445
• Molecular Formular: C30H38N6O12S
• Molecular Mass: 706.72072
• Monoisotopic Mass: 706.22684169
• SMILES: CSCC[C@H](NC(=O)[C@H](CC(=O)O)NC(=O)C)C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H](CC(=O)O)C(=O)Nc1ccc2c(c1)oc(=O)cc2C
• Canonical SMILES: CSCC[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)Nc1ccc2c(c1)oc(=O)cc2C)CC(=O)O)CCC(=O)N)NC(=O)[C@@H](NC(=O)C)CC(=O)O
• InChI: InChI=1S/C30H38N6O12S/c1-14-10-26(43)48-22-11-16(4-5-17(14)22)33-29(46)21(13-25(41)42)36-27(44)18(6-7-23(31)38)34-28(45)19(8-9-49-3)35-30(47)20(12-24(39)40)32-15(2)37/h4-5,10-11,18-21H,6-9,12-13H2,1-3H3,(H2,31,38)(H,32,37)(H,33,46)(H,34,45)(H,35,47)(H,36,44)(H,39,40)(H,41,42)/t18-,19-,20-,21-/m0/s1
• InChIKey: QJFJTAOSTJMQCI-TUFLPTIASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-3-{[(1S)-1-{[(1S)-3-carbamoyl-1-{[(1S)-2-carboxy-1-[(4-methyl-2-oxo-2H-chromen-7-yl)carbamoyl]ethyl]carbamoyl}propyl]carbamoyl}-3-(methylsulfanyl)propyl]carbamoyl}-3-acetamidopropanoic acid
• IUPAC Traditional name: (3S)-3-{[(1S)-1-{[(1S)-3-carbamoyl-1-{[(1S)-2-carboxy-1-[(4-methyl-2-oxochromen-7-yl)carbamoyl]ethyl]carbamoyl}propyl]carbamoyl}-3-(methylsulfanyl)propyl]carbamoyl}-3-acetamidopropanoic acid
• Synonyms: Ac-Asp-Met-Gln-Asp-AMC; Ac-DMQD-AMC; Ac-Asp-Met-Gln-Asp-7-Amino-4-Methylcoumarin

Database IDs

• PubChem SID: 162105577
• PubChem CID: 25108632

CALCULATED PROPERTIES

• Acid pKa: 3.4983559
• H Acceptors: 11
• H Donor: 8
• LogD (pH = 5.5): -5.959913
• LogD (pH = 7.4): -9.09533
• Log P: -2.6179001
• Molar Refractivity: 171.6553 cm^3
• Polarizability: 66.099174 Å^3
• Polar Surface Area: 289.49 Å^2
• Rotatable Bonds: 19
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03AMC144

A fluorogenic substrate for Caspase-3 and 6.

REFERENCES

• Ekert, P.G. et al., EMBO, 18(2):330 (1999).