N-methoxysuccinyl-alanyl-alanyl-prolyl-valine-4-nitroanilide
Basic information
- CAS
70967-90-7- Standard SMILES
COC(=O)CCC(=O)N[C@@H](C)C(=O)N[C@@H](C)C(=O)N1CCC[C@H]1C(=O)NC(=O)[C@@H](Nc1ccc([N+](=O)[O-])cc1)C(C)C- InChIKey
JWYKDZIEIWGSBN-OSAZLGQLSA-N- Molecular formula
- C27H38N6O9
- Average molar mass
- 590.6 g/mol
- Monoisotopic mass
- 590.27002681
Names & identifiers
- Preferred name
- N-methoxysuccinyl-alanyl-alanyl-prolyl-valine-4-nitroanilide
- IUPAC
- methyl 4-[[(2S)-1-[[(2S)-1-[(2S)-2-[[(2S)-3-methyl-2-(4-nitroanilino)butanoyl]carbamoyl]pyrrolidin-1-yl]-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]amino]-4-oxobutanoate
- English name
- N-METHOXYSUCCINYL-ALA-ALA-PRO-VAL P-NITROANILIDE
- Molecular formula
- C27H38N6O9
- Molecular weight
- 590.63
Names & synonyms
Meo-suc-ala-ala-pro-val-NAN-Methoxysuccinyl-alanyl-alanyl-prolyl-valine-4-nitroanilideN-Methoxysuccinyl-alanyl-alanyl-prolyl-valine-p-nitroanilideRefChem:163662N-methoxysuccinyl-Ala-Ala-Pro-Val-pNA70967-90-7Aapv-NAmethyl 4-[[(2S)-1-[[(2S)-1-[(2S)-2-[[(2S)-3-methyl-2-(4-nitroanilino)butanoyl]carbamoyl]pyrrolidin-1-yl]-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]amino]-4-oxobutanoateSCHEMBL29144618DTXSID30991270N-(4-Methoxy-1,4-dioxobutyl)-L-alanyl-L-alanyl-L-prolyl-N-(4-nitrophenyl)-L-valinamide(2S)-1-(N-{(2S)-1-Hydroxy-2-[(1-hydroxy-4-methoxy-4-oxobutylidene)amino]propylidene}-L-alanyl)-N-[N-(4-nitrophenyl)-L-valyl]pyrrolidine-2-carboximidic acid
Show more names
MEOSUC-ALA-ALA-PRO-VAL-PNAM4765MeOSuc-AAPV-pNALEUKOCYTE ESTERASE SUBSTRATEELASTASE SUBSTRATE I, COLORIMETRICMeOSuc-AAPV-pNA, Chromogenic SubstrateMEO-SUC-ALA-ALA-PRO-VAL-PARANITROANILIDE
Properties
Computed structural properties
- XLogP
- 1.5
- Topological polar surface area
- 209 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 10
- Rotatable bonds
- 13
- Heavy atoms
- 42
- Formal charge
- 0
- Complexity
- 1,020
Physicochemical properties
- Melting point
- 203 · 203-205°C
- Boiling point
- 958.4 · 958.4±65.0 °C(Predicted)
- Density
- 1.297 · 1.297±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · -20°C
- solubility
- 25 mg/mL, · DMF: 25 mg/mL, clear, light yellow
- form
- Off-white solid
- pka
- 13.29 · 13.29±0.20(Predicted)
- color
- White to Off-White
- Appearance
- White Solid
- Water Solubility
- 1 mg/mL · water: 1mg/mL
- BRN
- 6266359 · 6266359
- InChIKey
- YEGSVRNITOBIRO-OSAZLGQLSA-N
- SMILES
- C(N)(=O)[C@H](C(C)C)N(C(=O)[C@@H]1CCCN1C(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)CCC(OC)=O)C1=CC=C([N+]([O-])=O)C=C1
- UNSPSC Code
- 12352204 · 12352204
- NACRES
- 77 · NA.77
- Safety Statements
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Hazard information
Regulatory Information
L-Valinamide, N-(4-methoxy-1,4-dioxobutyl)-L-alanyl-L-alanyl-L-prolyl-N-(4-nitrophenyl)-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Safety data
- F
- 10-21
- wgk
- 3
- safety_code
- 22-24/25
- Storage Class
- 11 - Combustible Solids
Chemistry & industry
Applications
DescriptionProteinase 3 (PR3, myeloblastin) is a polymorphonuclear leukocyte serine proteinase that degrades matrix proteins including fibronectin, laminin, vitronectin, and collagen type IV to generate antimicrobial peptides. Neutrophil elastase is a serine proteinase that is secreted by neutrophils during inflammation to destroy pathogens. Evaluating these enzymes is helpful to understanding inflammatory autoimmune processes. MeOSuc-AAPV-pNA is a highly sensitive peptide substrate that is hydrolyzed by both human and mouse neutrophil elastase and PR3, but not cathepsin G or chymotrypsin. Enzyme activity can be quantified by colorimetric detection of free p-nitroanilide at 405 nm.
UsesN-Methoxysuccinyl-Ala-Ala-Pro-Val p-Nitroanilide is a highly sensitive peptide substrate that is hydrolyzed by both human and mouse neutrophil elastase and PR3 but not cathespin.
Related reactions
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Compound notes
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