(2,3-dihydroxypropoxy)[(2R)-3-(hexadecanoyloxy)-2-(octadec-9-enoyloxy)propoxy]phosphinic acid amine

• ChemBase ID: 154553
• Molecular Formular: C40H80NO10P
• Molecular Mass: 766.037661
• Monoisotopic Mass: 765.5519844
• SMILES: CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)OCC(CO)O)OC(=O)CCCCCCC/C=C/CCCCCCCC.N
• Canonical SMILES: CCCCCCCCCCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC/C=C/CCCCCCCC)COP(=O)(OCC(CO)O)O.N
• InChI: InChI=1S/C40H77O10P.H3N/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-40(44)50-38(36-49-51(45,46)48-34-37(42)33-41)35-47-39(43)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2;/h17-18,37-38,41-42H,3-16,19-36H2,1-2H3,(H,45,46);1H3/t37?,38-;/m1./s1
• InChIKey: WFYVYFVKHCDATR-KQWGQSANSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2,3-dihydroxypropoxy)[(2R)-3-(hexadecanoyloxy)-2-(octadec-9-enoyloxy)propoxy]phosphinic acid amine
• IUPAC Traditional name: 2,3-dihydroxypropoxy(2R)-3-(hexadecanoyloxy)-2-(octadec-9-enoyloxy)propoxyphosphinic acid amine
• Synonyms: (9Z)-9-Octadecenoic acid (1R)-1-[[[(2,3-dihydroxypropoxy)hydroxyphosphinyl]oxy]methyl]-2-[(1-oxohexadecyl)oxy]ethyl ester monoammonium salt; 1-Palmitoyl-2-oleoyl-sn-glycero-3-phosphoglycerol ammonium salt; 1-Hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1′-rac-glycerol) ammonium salt; L-α-Phosphatidyl-DL-glycerol, β-oleoyl-γ-palmitoyl ammonium salt; PG(16:0/18:1(9Z)); POPG-NH4; 2-Oleoyl-1-palmitoyl-sn-glycero-3-phospho-rac-(1-glycerol) ammonium salt

Database IDs

• CAS Number: 267228-70-6
• MDL Number: MFCD07437834
• PubChem SID: 162248691
• PubChem CID: 71311898

CALCULATED PROPERTIES

• Acid pKa: 1.8907738
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 9.112453
• LogD (pH = 7.4): 9.088186
• Log P: 11.464267
• Molar Refractivity: 205.6275 cm^3
• Polarizability: 82.05333 Å^3
• Polar Surface Area: 148.82 Å^2
• Rotatable Bonds: 41
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: chloroform: soluble20 mg/mL, clear, colorless

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

• Purity: ≥97.0% (TLC)
• Biological Source: from synthetic
• Empirical Formula (Hill Notation): C40H80NO10P

DETAILS

Sigma Aldrich - 76559

Application
POPG is widely used in studies as an ingredient in negatively charged synthetic lipid monolayers and bilayers.1