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

• ChemBase ID: 106444
• Molecular Formular: C33H44N6O12
• Molecular Mass: 716.73546
• Monoisotopic Mass: 716.30172088
• SMILES: CC(C)[C@H](NC(=O)C)C(=O)N[C@@H](CC(=O)O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](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](NC(=O)[C@H](C(C)C)NC(=O)[C@@H](NC(=O)[C@H](C(C)C)NC(=O)C)CC(=O)O)C
• InChI: InChI=1S/C33H44N6O12/c1-14(2)27(35-18(7)40)33(50)38-22(13-25(43)44)31(48)39-28(15(3)4)32(49)34-17(6)29(46)37-21(12-24(41)42)30(47)36-19-8-9-20-16(5)10-26(45)51-23(20)11-19/h8-11,14-15,17,21-22,27-28H,12-13H2,1-7H3,(H,34,49)(H,35,40)(H,36,47)(H,37,46)(H,38,50)(H,39,48)(H,41,42)(H,43,44)/t17-,21-,22-,27-,28-/m0/s1
• InChIKey: URUWHVCHYYJGHP-FEYJVYAOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-3-{[(1S)-1-{[(1S)-1-{[(1S)-2-carboxy-1-[(4-methyl-2-oxo-2H-chromen-7-yl)carbamoyl]ethyl]carbamoyl}ethyl]carbamoyl}-2-methylpropyl]carbamoyl}-3-[(2S)-2-acetamido-3-methylbutanamido]propanoic acid
• IUPAC Traditional name: (3S)-3-{[(1S)-1-{[(1S)-1-{[(1S)-2-carboxy-1-[(4-methyl-2-oxochromen-7-yl)carbamoyl]ethyl]carbamoyl}ethyl]carbamoyl}-2-methylpropyl]carbamoyl}-3-[(2S)-2-acetamido-3-methylbutanamido]propanoic acid
• Synonyms: Ac-Val-Asp-Val-Ala-Asp-AMC; Ac-VDVAD-AMC; Ac-Val-Asp-Val-Ala-Asp-7-Amino-4-Methylcoumarin

Database IDs

• PubChem SID: 162105459
• PubChem CID: 25108631

CALCULATED PROPERTIES

• Acid pKa: 3.597756
• H Acceptors: 11
• H Donor: 8
• LogD (pH = 5.5): -3.9104671
• LogD (pH = 7.4): -7.1510997
• Log P: -0.8707638
• Molar Refractivity: 177.2426 cm^3
• Polarizability: 68.499374 Å^3
• Polar Surface Area: 275.5 Å^2
• Rotatable Bonds: 17
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03AMC142

A fluorogenic substrate for Caspase-2.

REFERENCES

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