3-(2-{2-[2-acetamido-3-(4-hydroxyphenyl)propanamido]-3-methylbutanamido}propanamido)-3-[(4-methyl-2-oxo-2H-chromen-7-yl)carbamoyl]propanoic acid

• ChemBase ID: 106005
• Molecular Formular: C33H39N5O10
• Molecular Mass: 665.69026
• Monoisotopic Mass: 665.26969247
• SMILES: CC(C)C(NC(=O)C(Cc1ccc(O)cc1)NC(=O)C)C(=O)NC(C)C(=O)NC(CC(=O)O)C(=O)Nc1cc2c(cc1)c(C)cc(=O)o2
• Canonical SMILES: OC(=O)CC(C(=O)Nc1ccc2c(c1)oc(=O)cc2C)NC(=O)C(NC(=O)C(C(C)C)NC(=O)C(Cc1ccc(cc1)O)NC(=O)C)C
• InChI: InChI=1S/C33H39N5O10/c1-16(2)29(38-32(46)24(35-19(5)39)13-20-6-9-22(40)10-7-20)33(47)34-18(4)30(44)37-25(15-27(41)42)31(45)36-21-8-11-23-17(3)12-28(43)48-26(23)14-21/h6-12,14,16,18,24-25,29,40H,13,15H2,1-5H3,(H,34,47)(H,35,39)(H,36,45)(H,37,44)(H,38,46)(H,41,42)
• InChIKey: YGLOALWHJIANIH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(2-{2-[2-acetamido-3-(4-hydroxyphenyl)propanamido]-3-methylbutanamido}propanamido)-3-[(4-methyl-2-oxo-2H-chromen-7-yl)carbamoyl]propanoic acid
• IUPAC Traditional name: 3-(2-{2-[2-acetamido-3-(4-hydroxyphenyl)propanamido]-3-methylbutanamido}propanamido)-3-[(4-methyl-2-oxochromen-7-yl)carbamoyl]propanoic acid
• Synonyms: Acetyl-YVAD-AMC; IL-1 β Converting Enzyme Fluorogenic Substrate; ICE SUBSTRATE III; Ac-YVAD-AMC; N-Acetyl-Tyr-Val-Ala-Asp-7-amido-4-methylcoumarin

Database IDs

• CAS Number: 149231-65-2
• MDL Number: MFCD00171369
• PubChem SID: 24890658; 162092861
• PubChem CID: 4337

CALCULATED PROPERTIES

• Acid pKa: 3.697657
• H Acceptors: 9
• H Donor: 7
• LogD (pH = 5.5): -1.0282798
• LogD (pH = 7.4): -2.5369918
• Log P: 0.77283293
• Molar Refractivity: 171.5141 cm^3
• Polarizability: 65.76104 Å^3
• Polar Surface Area: 229.33 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: soluble10 mM (The solution is stable in the dark at -20 °C for more than 1 month if no water is present.)
• Apperance: powder

Safety Information

• Storage Condition: -20°C
• German water hazard class: 3
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: human ... CASP1(834), CASP4(837)mouse ... CASP1(12362), CASP4(12363)rat ... CASP1(25166), CASP4(114555)

Product Information

• Purity: ≥97%; ≥99% (TLC)
• Compostion: Peptide content, ≥80%

DETAILS

MP Biomedicals - 02195849

N-Acetyl-Tyr-Val-Ala-Asp-AMC
Purity: >97%
Fluorogenic substrate for ICE.
Excitation = 380 nm; Emission = 460 nm.

Sigma Aldrich - A2452

Amino Acid Sequence
NAc-Tyr-Val-Ala-Asp-AMC
Caution
The lyophilized powder is stable below 0 °C for more than one year if kept dry and protected from light.
Substrates
Fluorogenic substrate for caspase 1 (Km = 14 μM) and caspase 4 (TX), cysteine proteases involved in apoptosis and inflammation.