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

• ChemBase ID: 118843
• Molecular Formular: C16H16N2O2
• Molecular Mass: 268.31044
• Monoisotopic Mass: 268.12117776
• SMILES: C(=C\c1cc2c3c(c1)CCCN3CCC2)(\C(=O)O)/C#N
• Canonical SMILES: N#C/C(=C/c1cc2CCCN3c2c(c1)CCC3)/C(=O)O
• InChI: InChI=1S/C16H16N2O2/c17-10-14(16(19)20)9-11-7-12-3-1-5-18-6-2-4-13(8-11)15(12)18/h7-9H,1-6H2,(H,19,20)/b14-9-
• InChIKey: JXENNHTVELFRHV-ZROIWOOFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2Z)-3-{1-azatricyclo[7.3.1.0^5,^1^3]trideca-5,7,9(13)-trien-7-yl}-2-cyanoprop-2-enoic acid; 3-{1-azatricyclo[7.3.1.0^5,^1^3]trideca-5,7,9(13)-trien-7-yl}-2-cyanoprop-2-enoic acid
• IUPAC Traditional name: (2Z)-3-{1-azatricyclo[7.3.1.0^5,^1^3]trideca-5,7,9(13)-trien-7-yl}-2-cyanoprop-2-enoic acid; 3-{1-azatricyclo[7.3.1.0^5,^1^3]trideca-5,7,9(13)-trien-7-yl}-2-cyanoprop-2-enoic acid
• Synonyms: (2Z)-2-cyano-3-(2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinolin-9-yl)acrylic acid; 9-([E]-2-Carboxy-2-cyanovinyl)julolidine; CCVJ; 9-(2-Carboxy-2-cyanovinyl)julolidine

Database IDs

• CAS Number: 142978-18-5
• MDL Number: MFCD00274408; MFCD14584925
• PubChem SID: 162102823; 24886383
• PubChem CID: 45497365

CALCULATED PROPERTIES

• Acid pKa: 2.7652545
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 0.5346365
• LogD (pH = 7.4): -0.44552946
• Log P: 1.2530572
• Molar Refractivity: 78.3633 cm^3
• Polarizability: 28.453712 Å^3
• Polar Surface Area: 64.33 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: chloroform: soluble; DMSO: soluble
• Partition Coefficient: 2.318
• Fluorescence: λex 433 nm; λem 500 nm in 50 mM Tris pH 8.0; 40% glycerol

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥97.0% (HPLC); 95+%
• Suitability: suitable for fluorescence
• Product Line: BioReagent
• Empirical Formula (Hill Notation): C16H16N2O2

DETAILS

Sigma Aldrich - 72301

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