4-azido-N-[2-({2-[(4-azido-2-hydroxyphenyl)formamido]ethyl}disulfanyl)ethyl]-2-hydroxybenzamide

• ChemBase ID: 155990
• Molecular Formular: C18H18N8O4S2
• Molecular Mass: 474.51672
• Monoisotopic Mass: 474.0892431
• SMILES: c1cc(c(cc1N=[N+]=[N-])O)C(=O)NCCSSCCNC(=O)c1ccc(cc1O)N=[N+]=[N-]
• Canonical SMILES: [N-]=[N+]=Nc1ccc(c(c1)O)C(=O)NCCSSCCNC(=O)c1ccc(cc1O)N=[N+]=[N-]
• InChI: InChI=1S/C18H18N8O4S2/c19-25-23-11-1-3-13(15(27)9-11)17(29)21-5-7-31-32-8-6-22-18(30)14-4-2-12(24-26-20)10-16(14)28/h1-4,9-10,27-28H,5-8H2,(H,21,29)(H,22,30)
• InChIKey: QQZOUYFHWKTGEY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-azido-N-[2-({2-[(4-azido-2-hydroxyphenyl)formamido]ethyl}disulfanyl)ethyl]-2-hydroxybenzamide
• IUPAC Traditional name: 4-azido-N-[2-({2-[(4-azido-2-hydroxyphenyl)formamido]ethyl}disulfanyl)ethyl]-2-hydroxybenzamide
• Synonyms: BASED; N, N′-(Dithiobis-ethylene)bis(4-azido-2-hydroxy-benzamide); N,N′-Bis(4-azidosalicoyl)cystamine; Bis[2-(4-azidosalicylamido)ethyl] disulfide

Database IDs

• CAS Number: 199804-21-2
• MDL Number: MFCD01861964
• PubChem SID: 24864027; 162250128
• PubChem CID: 3658531

CALCULATED PROPERTIES

• Acid pKa: 7.346131
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): 3.8926814
• LogD (pH = 7.4): 3.5134041
• Log P: 4.1268873
• Molar Refractivity: 127.9776 cm^3
• Polarizability: 44.970158 Å^3
• Polar Surface Area: 157.52 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥95.0% (HPLC)
• Empirical Formula (Hill Notation): C18H18N8O4S2

DETAILS

Sigma Aldrich - 38545

Application
Reagent for cross linking of proteins; the cross link can be cleaved1