(3S)-3-[(2S)-2-[(2S)-2-[(2S)-2-{[(benzyloxy)carbonyl]amino}-3-(4-hydroxyphenyl)propanamido]-3-methylbutanamido]propanamido]-3-[(4-methoxynaphthalen-2-yl)carbamoyl]propanoic acid

• ChemBase ID: 106584
• Molecular Formular: C40H45N5O10
• Molecular Mass: 755.8128
• Monoisotopic Mass: 755.31664267
• SMILES: COc1cc(NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](C)NC(=O)[C@@H](NC(=O)[C@H](Cc2ccc(cc2)O)NC(=O)OCc2ccccc2)C(C)C)cc2c1cccc2
• Canonical SMILES: COc1cc(NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](C(C)C)NC(=O)[C@H](Cc2ccc(cc2)O)NC(=O)OCc2ccccc2)C)CC(=O)O)cc2c1cccc2
• InChI: InChI=1S/C40H45N5O10/c1-23(2)35(45-38(51)31(18-25-14-16-29(46)17-15-25)44-40(53)55-22-26-10-6-5-7-11-26)39(52)41-24(3)36(49)43-32(21-34(47)48)37(50)42-28-19-27-12-8-9-13-30(27)33(20-28)54-4/h5-17,19-20,23-24,31-32,35,46H,18,21-22H2,1-4H3,(H,41,52)(H,42,50)(H,43,49)(H,44,53)(H,45,51)(H,47,48)/t24-,31-,32-,35-/m0/s1
• InChIKey: LMBMRCCDZFOBGB-CCVFUZGKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-3-[(2S)-2-[(2S)-2-[(2S)-2-{[(benzyloxy)carbonyl]amino}-3-(4-hydroxyphenyl)propanamido]-3-methylbutanamido]propanamido]-3-[(4-methoxynaphthalen-2-yl)carbamoyl]propanoic acid
• IUPAC Traditional name: (3S)-3-[(2S)-2-[(2S)-2-[(2S)-2-{[(benzyloxy)carbonyl]amino}-3-(4-hydroxyphenyl)propanamido]-3-methylbutanamido]propanamido]-3-[(4-methoxynaphthalen-2-yl)carbamoyl]propanoic acid
• Synonyms: Z-Tyr-Val-Ala-Asp-MNA; Z-YVAD-MNA; Z-Tyr-Val-Ala-Asp-4-Methoxy-2-Naphthylamine

Database IDs

• PubChem SID: 162105993
• PubChem CID: 25108737

CALCULATED PROPERTIES

• Acid pKa: 3.8695846
• H Acceptors: 9
• H Donor: 7
• LogD (pH = 5.5): 2.203828
• LogD (pH = 7.4): 0.60645163
• Log P: 3.8388944
• Molar Refractivity: 200.8911 cm^3
• Polarizability: 78.72613 Å^3
• Polar Surface Area: 221.49 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03MNA120

A fluorogenic/colorimetric substrate for Caspase-1 and 4.

REFERENCES

• Marcelli, M. et al., Can. Res., 58:76 (1998).