2,5-dioxopyrrolidin-1-yl 3-{[(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]carbamoyl}propanoate

• ChemBase ID: 158619
• Molecular Formular: C31H42N2O9
• Molecular Mass: 586.67318
• Monoisotopic Mass: 586.28903093
• 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)NC(=O)CCC(=O)ON1C(=O)CCC1=O
• Canonical SMILES: O=C(N[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)CCC(=O)ON1C(=O)CCC1=O
• InChI: InChI=1S/C31H42N2O9/c1-29-11-9-19(32-24(35)5-8-27(38)42-33-25(36)6-7-26(33)37)14-18(29)3-4-21-22(29)15-23(34)30(2)20(10-12-31(21,30)40)17-13-28(39)41-16-17/h13,18-23,34,40H,3-12,14-16H2,1-2H3,(H,32,35)/t18-,19+,20-,21-,22+,23-,29+,30+,31+/m1/s1
• InChIKey: AVQGRLJRQILBRQ-ZCIIQETRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,5-dioxopyrrolidin-1-yl 3-{[(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]carbamoyl}propanoate
• IUPAC Traditional name: 2,5-dioxopyrrolidin-1-yl 3-{[(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]carbamoyl}propanoate
• Synonyms: (3β,5β,12β)-3-[[4-[(2,5-Dioxo-1-pyrrolidinyl)oxy]-1,4-dioxobutyl]amino]-12,14-dihydroxycard-20(22)-enolide; 3β-Amino-3-deoxydigitoxigenin Hemisuccinate N-Succinimidyl Ester; 3-Amino-3-deoxydigoxigenin hemisuccinamide, succinimidyl ester

Database IDs

• CAS Number: 216299-46-6
• MDL Number: MFCD00467357
• PubChem SID: 162252755
• PubChem CID: 71312664

CALCULATED PROPERTIES

• Acid pKa: 7.1511164
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): 0.73337615
• LogD (pH = 7.4): 0.3007781
• Log P: 0.74295646
• Molar Refractivity: 147.7045 cm^3
• Polarizability: 58.627586 Å^3
• Polar Surface Area: 159.54 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Shipped in: dry ice
• Mol. Weight: mol wt 586.68

DETAILS

Sigma Aldrich - A0223

Application
Amine-reactive haptenylation reagent. This succinimidyl ester derivative of digoxigenin has been shown to inhibit the Na+/K+- ATPase by binding to the cardiac steroid receptor site.

Toronto Research Chemicals - A603820

A Digoxigenin derivative with cardiotonic activity.

REFERENCES

• Tanaka, M., et al.: J. Biotech., 5, 209 (1987)
• Nada, M., et al.: Lipids, 129, 517 (1987)
• Mofid, M., et al.: J. Biol. Chem., 2 277 (1987)