[(2R)-2,3-bis(hexadecanoyloxy)propoxy]({[(1S,2R,3R,4S,5S,6R)-2,3,4,5,6-pentahydroxycyclohexyl]oxy})phosphinic acid

• ChemBase ID: 153690
• Molecular Formular: C41H79O13P
• Molecular Mass: 811.031921
• Monoisotopic Mass: 810.52582922
• SMILES: CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)O[C@@H]1[C@@H]([C@@H]([C@H]([C@@H]([C@H]1O)O)O)O)O)OC(=O)CCCCCCCCCCCCCCC
• Canonical SMILES: CCCCCCCCCCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCCCCCCCCCC)COP(=O)(O[C@@H]1[C@H](O)[C@H](O)[C@H]([C@@H]([C@H]1O)O)O)O
• InChI: InChI=1S/C41H79O13P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-34(42)51-31-33(32-52-55(49,50)54-41-39(47)37(45)36(44)38(46)40(41)48)53-35(43)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h33,36-41,44-48H,3-32H2,1-2H3,(H,49,50)/t33-,36-,37-,38+,39-,40-,41-/m1/s1
• InChIKey: IBUKXRINTKQBRQ-KCKFLZCVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R)-2,3-bis(hexadecanoyloxy)propoxy]({[(1S,2R,3R,4S,5S,6R)-2,3,4,5,6-pentahydroxycyclohexyl]oxy})phosphinic acid
• IUPAC Traditional name: (2R)-2,3-bis(hexadecanoyloxy)propoxy[(1S,2R,3R,4S,5S,6R)-2,3,4,5,6-pentahydroxycyclohexyl]oxyphosphinic acid
• Synonyms: 1,2-Dihexadecanoyl-sn-glycero-3-phospho-(1-D-myo-inositol); DPPI; L-α-Phosphatidylinositol dipalmitoyl ammonium salt

Database IDs

• MDL Number: MFCD02259151
• PubChem SID: 162247829
• PubChem CID: 644003

CALCULATED PROPERTIES

• Acid pKa: 1.8332553
• H Acceptors: 9
• H Donor: 6
• LogD (pH = 5.5): 6.6392674
• LogD (pH = 7.4): 6.6179314
• Log P: 8.994056
• Molar Refractivity: 210.5678 cm^3
• Polarizability: 85.35403 Å^3
• Polar Surface Area: 209.51 Å^2
• Rotatable Bonds: 38
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: insoluble; organic solvents: soluble

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: ≥98% (TLC)
• Empirical Formula (Hill Notation): C41H82NO13P

DETAILS

Sigma Aldrich - P1368

General description
Synthetic analog of the natural phosphatidyl inositols with C16:0 saturated fatty acids and the same inositol and diacyl glycerol stereochemistry as that of the natural compound.
Reconstitution
Can be dispersed by sonication to form an opaque but homogeneous preparation.