3-({2-[(4-azido-2-hydroxyphenyl)formamido]ethyl}disulfanyl)propanoic acid

• ChemBase ID: 161045
• Molecular Formular: C12H14N4O4S2
• Molecular Mass: 342.39396
• Monoisotopic Mass: 342.04564695
• SMILES: OC(=O)CCSSCCNC(=O)c1ccc(cc1O)N=[N+]=[N-]
• Canonical SMILES: [N-]=[N+]=Nc1ccc(c(c1)O)C(=O)NCCSSCCC(=O)O
• InChI: InChI=1S/C12H14N4O4S2/c13-16-15-8-1-2-9(10(17)7-8)12(20)14-4-6-22-21-5-3-11(18)19/h1-2,7,17H,3-6H2,(H,14,20)(H,18,19)
• InChIKey: AOMOESAZLQVHAJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-({2-[(4-azido-2-hydroxyphenyl)formamido]ethyl}disulfanyl)propanoic acid
• IUPAC Traditional name: 3-({2-[(4-azido-2-hydroxyphenyl)formamido]ethyl}disulfanyl)propanoic acid
• Synonyms: 3-[[2-[(4-Azido-2-hydroxybenzoyl)amino]ethyl]dithio]propanoic Acid; (p-Azidosalicylamido)ethyl-1,3'-dithiopropionic Acid

Database IDs

• CAS Number: 107426-70-0
• PubChem SID: 162255180
• PubChem CID: 29972446

CALCULATED PROPERTIES

• Acid pKa: 3.9381917
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 0.7418139
• LogD (pH = 7.4): -1.0723954
• Log P: 2.4277432
• Molar Refractivity: 88.3186 cm^3
• Polarizability: 32.042294 Å^3
• Polar Surface Area: 116.06 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Methanol
• Apperance: Brown Solid

DETAILS

Toronto Research Chemicals - A858950

A photo-reactive heterobifunctional cross-linker.

REFERENCES

• Kerrigan, S. and Brooks, D.E.: Bioconjugate Chem. 9,596-603 (1998)