4-azido-2-hydroxy-3,5-diiodo-N-[2-(pyridin-2-yldisulfanyl)ethyl]benzamide

• ChemBase ID: 171670
• Molecular Formular: C14H11I2N5O2S2
• Molecular Mass: 599.20838
• Monoisotopic Mass: 598.84436262
• SMILES: n1ccccc1SSCCNC(=O)c1c(c(c(c(c1)I)N=[N+]=[N-])I)O
• Canonical SMILES: [N-]=[N+]=Nc1c(I)cc(c(c1I)O)C(=O)NCCSSc1ccccn1
• InChI: InChI=1S/C14H11I2N5O2S2/c15-9-7-8(13(22)11(16)12(9)20-21-17)14(23)19-5-6-24-25-10-3-1-2-4-18-10/h1-4,7,22H,5-6H2,(H,19,23)
• InChIKey: CKOHBPRDAGSGHJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-azido-2-hydroxy-3,5-diiodo-N-[2-(pyridin-2-yldisulfanyl)ethyl]benzamide
• IUPAC Traditional name: 4-azido-2-hydroxy-3,5-diiodo-N-[2-(pyridin-2-yldisulfanyl)ethyl]benzamide
• Synonyms: IAET; 4-Azido-2-hydroxy-3,5-diiodo-N-[2-(2-pyridinyldithio)ethyl]benzamide; S-[2-(Iodo-4-Azidosalicylamido)ethylthio]-2-thiopyridine

Database IDs

• CAS Number: 175093-14-8
• PubChem SID: 164227580
• PubChem CID: 45039578

CALCULATED PROPERTIES

• Acid pKa: 6.17311
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 5.3877916
• LogD (pH = 7.4): 4.2858677
• Log P: 5.58499
• Molar Refractivity: 120.1005 cm^3
• Polarizability: 45.215225 Å^3
• Polar Surface Area: 91.65 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - I688000

IAET is a cleavable, photoactivable cross linking agent. The maximum length of the linker arm between Ca of the amino acid of interest and the photoreactive atom is 14A. The IAET absorbance maxima are: l max = 273nm; e= 2.3 x 104 ; l max = 343nm;

REFERENCES

• Ebright, Y.W., et al.: Bioconjugate Chem., 7(3)
• 381-384 (1996)