2,5-dioxopyrrolidin-1-yl 3-{1-azatricyclo[7.3.1.05,13]trideca-5,7,9(13)-trien-7-yl}-2-cyanoprop-2-enoate

• ChemBase ID: 156829
• Molecular Formular: C20H19N3O4
• Molecular Mass: 365.38256
• Monoisotopic Mass: 365.1375561
• SMILES: c1c(cc2c3c1CCCN3CCC2)/C=C(\C#N)/C(=O)ON1C(=O)CCC1=O
• Canonical SMILES: N#C/C(=C\c1cc2CCCN3c2c(c1)CCC3)/C(=O)ON1C(=O)CCC1=O
• InChI: InChI=1S/C20H19N3O4/c21-12-16(20(26)27-23-17(24)5-6-18(23)25)11-13-9-14-3-1-7-22-8-2-4-15(10-13)19(14)22/h9-11H,1-8H2
• InChIKey: UBEGWDBDEXAGSI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,5-dioxopyrrolidin-1-yl 3-{1-azatricyclo[7.3.1.0^5,^1^3]trideca-5,7,9(13)-trien-7-yl}-2-cyanoprop-2-enoate
• IUPAC Traditional name: 2,5-dioxopyrrolidin-1-yl 3-{1-azatricyclo[7.3.1.0^5,^1^3]trideca-5,7,9(13)-trien-7-yl}-2-cyanoprop-2-enoate
• Synonyms: 9-(2-Carboxy-2-cyanovinyl)julolidine N-succinimidylester

Database IDs

• MDL Number: MFCD03703569
• PubChem SID: 162250966
• PubChem CID: 6249078

CALCULATED PROPERTIES

• Acid pKa: 17.694685
• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): 2.5811913
• LogD (pH = 7.4): 2.6272025
• Log P: 2.627822
• Molar Refractivity: 98.9171 cm^3
• Polarizability: 36.68031 Å^3
• Polar Surface Area: 90.71 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: methylene chloride: soluble
• Fluorescence: λex 433 nm; λem 515 nm in 50 mM Tris pH 8.0; 40% glycerol

Safety Information

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

Product Information

• Purity: ≥95% (HPLC)
• Empirical Formula (Hill Notation): C20H19N3O4

DETAILS

Sigma Aldrich - 92488

Application
Fluorescent probe for binding to proteins etc., quantum yield increases by decreasing free rotation.