2,5-dioxopyrrolidin-1-yl 6-(2-{[(1S,2S,5S,7R,10R,11S,14R,15S,16R)-11,16-dihydroxy-2,15-dimethyl-14-(5-oxo-2,5-dihydrofuran-3-yl)tetracyclo[8.7.0.02,7.011,15]heptadecan-5-yl]oxy}acetamido)hexanoate

• ChemBase ID: 153717
• Molecular Formular: C35H50N2O10
• Molecular Mass: 658.7789
• Monoisotopic Mass: 658.34654581
• SMILES: C[C@]12CC[C@@H](C[C@H]1CC[C@@H]1[C@@H]2C[C@H]([C@]2([C@@]1(CC[C@@H]2C1=CC(=O)OC1)O)C)O)OCC(=O)NCCCCCC(=O)ON1C(=O)CCC1=O
• Canonical SMILES: O=C(CO[C@H]1CC[C@]2([C@@H](C1)CC[C@@H]1[C@@H]2C[C@@H](O)[C@]2([C@]1(O)CC[C@@H]2C1=CC(=O)OC1)C)C)NCCCCCC(=O)ON1C(=O)CCC1=O
• InChI: InChI=1S/C35H50N2O10/c1-33-13-11-23(45-20-28(39)36-15-5-3-4-6-31(42)47-37-29(40)9-10-30(37)41)17-22(33)7-8-25-26(33)18-27(38)34(2)24(12-14-35(25,34)44)21-16-32(43)46-19-21/h16,22-27,38,44H,3-15,17-20H2,1-2H3,(H,36,39)/t22-,23+,24-,25-,26+,27-,33+,34+,35+/m1/s1
• InChIKey: KHNDABJZSPPYLE-FUGFVFQCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,5-dioxopyrrolidin-1-yl 6-(2-{[(1S,2S,5S,7R,10R,11S,14R,15S,16R)-11,16-dihydroxy-2,15-dimethyl-14-(5-oxo-2,5-dihydrofuran-3-yl)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-5-yl]oxy}acetamido)hexanoate
• IUPAC Traditional name: 2,5-dioxopyrrolidin-1-yl 6-(2-{[(1S,2S,5S,7R,10R,11S,14R,15S,16R)-11,16-dihydroxy-2,15-dimethyl-14-(5-oxo-2H-furan-3-yl)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-5-yl]oxy}acetamido)hexanoate
• Synonyms: ε-(Digoxigenin-3-0-acetamido)caproic acid N-hydroxysuccinimide ester; DIG NHS; Digoxigenin NHS-ester

Database IDs

• CAS Number: 129273-26-3
• MDL Number: MFCD02093394
• PubChem SID: 162247856; 24879762
• PubChem CID: 16217173

CALCULATED PROPERTIES

• Acid pKa: 7.1511164
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): 1.6271869
• LogD (pH = 7.4): 1.1945884
• Log P: 1.6367668
• Molar Refractivity: 168.0056 cm^3
• Polarizability: 66.678024 Å^3
• Polar Surface Area: 168.77 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• European Hazard Symbols: Highly toxic (T+)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 1
• Risk Statements: 26/27/28-33
• Safety Statements: 28-36/37-45
• GHS Pictograms: GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H300-H310-H330-H373
• GHS Precautionary statements: P260-P264-P280-P284-P301 + P310-P302 + P350
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 1
• Storage Temperature: -20°C

Product Information

• Purity: ≥80% (HPLC)
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C35H50N2O10

DETAILS

Sigma Aldrich - 55865

Application
The activated ester reacts with amino groups under mild conditions, attaching the digoxigenin moiety to proteins or 5’-amino substituted oligonucleotides1,2,3