methyl 3-{[(1S)-1-{[(2S)-1-[(2S)-2-{[(1S)-2-methyl-1-[(4-nitrophenyl)carbamoyl]propyl]carbamoyl}pyrrolidin-1-yl]-1-oxopropan-2-yl]carbamoyl}ethyl]carbamoyl}propanoate

• ChemBase ID: 106628
• Molecular Formular: C27H38N6O9
• Molecular Mass: 590.62542
• Monoisotopic Mass: 590.27002683
• SMILES: COC(=O)CCC(=O)N[C@@H](C)C(=O)N[C@@H](C)C(=O)N1CCC[C@H]1C(=O)N[C@@H](C(C)C)C(=O)Nc1ccc(cc1)[N+](=O)[O-]
• Canonical SMILES: COC(=O)CCC(=O)N[C@H](C(=O)N[C@H](C(=O)N1CCC[C@H]1C(=O)N[C@H](C(=O)Nc1ccc(cc1)[N+](=O)[O-])C(C)C)C)C
• InChI: InChI=1S/C27H38N6O9/c1-15(2)23(26(38)30-18-8-10-19(11-9-18)33(40)41)31-25(37)20-7-6-14-32(20)27(39)17(4)29-24(36)16(3)28-21(34)12-13-22(35)42-5/h8-11,15-17,20,23H,6-7,12-14H2,1-5H3,(H,28,34)(H,29,36)(H,30,38)(H,31,37)/t16-,17-,20-,23-/m0/s1
• InChIKey: VLVGCNNWNUERRZ-OSAZLGQLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl 3-{[(1S)-1-{[(2S)-1-[(2S)-2-{[(1S)-2-methyl-1-[(4-nitrophenyl)carbamoyl]propyl]carbamoyl}pyrrolidin-1-yl]-1-oxopropan-2-yl]carbamoyl}ethyl]carbamoyl}propanoate
• IUPAC Traditional name: methyl 3-{[(1S)-1-{[(2S)-1-[(2S)-2-{[(1S)-2-methyl-1-[(4-nitrophenyl)carbamoyl]propyl]carbamoyl}pyrrolidin-1-yl]-1-oxopropan-2-yl]carbamoyl}ethyl]carbamoyl}propanoate
• Synonyms: N-(Methoxysuccinyl)-L-alanyl-L-alanyl-L-prolyl-L-valine 4-nitroanilide; N-(Methoxysuccinyl)-Ala-Ala-Pro-Val 4-nitroanilide; N-Methoxysuccinyl-Ala-Ala-Pro-Val p-nitroanilide; MeOSuc-Ala-Ala-Pro-Val-PNA; MeOSuc-AAPV-PNA; MeOSuc-Ala-Ala-Pro-Val-paranitroanilide

Database IDs

• CAS Number: 70967-90-7
• MDL Number: MFCD00077137
• Beilstein Number: 6266359
• PubChem SID: 24896943; 162089029
• PubChem CID: 16219658

CALCULATED PROPERTIES

• Acid pKa: 11.682319
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): 0.1357817
• LogD (pH = 7.4): 0.13576175
• Log P: 0.13578199
• Molar Refractivity: 149.7824 cm^3
• Polarizability: 57.16884 Å^3
• Polar Surface Area: 208.83 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMF: soluble25 mg/mL, clear, light yellow

Safety Information

• German water hazard class: 3
• Safety Statements: 22-24/25
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥97.0% (HPLC)
• Quality Level: PREMIUM
• Empirical Formula (Hill Notation): C27H38N6O9

DETAILS

MP Biomedicals - 03PNA094

A specific chromogenic substrate for human neutrophil elastase (Kcat/Km = 120,000 vs. 2700 for pancreatic elastase). Cleavage can be monitored at ~410 nm. Sold on the basis of substrate content.

Sigma Aldrich - M4765

Substrates
Substrate for human leukocyte elastase.

Sigma Aldrich - 65352

Other Notes
Sensitive substrate for elastase from human leukocytes and porcine pancreas1

REFERENCES

• Thornberry, N.A. et al., Science, 281:1312 (1998).
• Thornberry, N.A. et al., J. Biol. Chem., 272:17907 (1997).
• Barrett, A.J., et al. 1989. Biochim. J. 260, 259.
• Nakajima, K., et al. 1979. J. Biol. Chem. 254, 4027.