(2-hydroxyethoxy)[2-(octadec-9-enoyloxy)-3-(octadecanoyloxy)propoxy]phosphinic acid

• ChemBase ID: 105174
• Molecular Formular: C41H79O9P
• Molecular Mass: 747.034321
• Monoisotopic Mass: 746.54617074
• SMILES: CCCCCCCCCCCCCCCCCC(=O)OCC(COP(=O)(O)OCCO)OC(=O)CCCCCCC/C=C/CCCCCCCC
• Canonical SMILES: CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCC/C=C/CCCCCCCC)COP(=O)(OCCO)O
• InChI: InChI=1S/C41H79O9P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-40(43)47-37-39(38-49-51(45,46)48-36-35-42)50-41(44)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h18,20,39,42H,3-17,19,21-38H2,1-2H3,(H,45,46)
• InChIKey: AMEJPUGXIIBJEX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2-hydroxyethoxy)[2-(octadec-9-enoyloxy)-3-(octadecanoyloxy)propoxy]phosphinic acid
• IUPAC Traditional name: 2-hydroxyethoxy(2-(octadec-9-enoyloxy)-3-(octadecanoyloxy)propoxy)phosphinic acid
• Synonyms: 1-Palmitoyl-2-oleoyl-sn-glycero-3-phosphoethanol; PHOSPHATIDYLETHANOL

Database IDs

• PubChem SID: 162105863
• PubChem CID: 71300188

CALCULATED PROPERTIES

• Acid pKa: 1.894312
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 10.632121
• LogD (pH = 7.4): 10.607661
• Log P: 12.98374
• Molar Refractivity: 208.867 cm^3
• Polarizability: 83.257286 Å^3
• Polar Surface Area: 128.59 Å^2
• Rotatable Bonds: 42
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• Storage Condition: -20°C, Store Under Nitrogen

Product Information

• Purity: 98%

DETAILS

MP Biomedicals - 02158983

Purity: 98%
Used as a chromatographic standard to assay PLD activity in intact cells via the conversion of phosphatidylcholine to phosphatidylethanol by phospholipase D in the presence of ethanol.

REFERENCES

• Kobayashi, M. and Kanfer, J.N., J. Neurochem. , 48 : 1597 (1987).
• Gustavsson, L. and Alling, C., Biochem. Biophys. Res. Commun. , 142 : 958 (1987).
• Liscovitch, M., Biol. Chem. , 264 : 1450 (1989).
• Pai, J.-K., et al., ibid. , 263 : 12472 (1988).