1-[(9Z)-octadec-9-enoyloxy]-2,5-dioxopyrrolidine-3-sulfonic acid

• ChemBase ID: 177922
• Molecular Formular: C22H37NO7S
• Molecular Mass: 459.59668
• Monoisotopic Mass: 459.22907353
• SMILES: C(CCCCCC/C=C\CCCCCCCC)C(=O)ON1C(=O)CC(C1=O)S(=O)(=O)O
• Canonical SMILES: CCCCCCCC/C=C\CCCCCCCC(=O)ON1C(=O)CC(C1=O)S(=O)(=O)O
• InChI: InChI=1S/C22H37NO7S/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(25)30-23-20(24)18-19(22(23)26)31(27,28)29/h9-10,19H,2-8,11-18H2,1H3,(H,27,28,29)/b10-9-
• InChIKey: LFZDKQJJMZRWMV-KTKRTIGZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(9Z)-octadec-9-enoyloxy]-2,5-dioxopyrrolidine-3-sulfonic acid
• IUPAC Traditional name: 1-[(9Z)-octadec-9-enoyloxy]-2,5-dioxopyrrolidine-3-sulfonic acid
• Synonyms: 2,5-Dioxo-1-[[(9Z)-1-oxo-9-octadecenyl]oxy]-3-pyrrolidinesulfonic Acid Sodium; (Z)-2,5-Dioxo-1-[(1-oxo-9-octadecenyl)oxy]-3-pyrrolidinesulfonic Acid Sodium; Sulfosuccinimidyl Oleate Sodium

Database IDs

• CAS Number: 135661-44-8
• PubChem SID: 164233832
• PubChem CID: 46782948

CALCULATED PROPERTIES

• Acid pKa: -1.3764983
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 3.076609
• LogD (pH = 7.4): 3.0763943
• Log P: 5.4529967
• Molar Refractivity: 117.9358 cm^3
• Polarizability: 47.02529 Å^3
• Polar Surface Area: 118.05 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol (Sparingly)
• Apperance: White to Off-White Solid
• Melting Point: >220°C (dec.)

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - S689200

A long-chain fatty acid; inhibition of fatty acid transport.

REFERENCES

• Giedroc, D., et al.: J. Biol. Chem., 258, 16 (1983)
• Harmon, C, et al.: J. Membr. Biol., 121, 261 (1983)
• Abumrad, N., et al.: J. Biol. Chem., 268, 17665 (1983)
• Hamilton, J., et al.: J. Lipid. Res., 39, 467 (1983)
• Luiken, J., et al.: Am. J. Physiol. End