triammonium (1R,2R,3S,4R,5R,6S)-4-({[(2R)-2,3-bis(hexadecanoyloxy)propoxy]phosphinato}oxy)-2-(hydrogen phosphonatooxy)-3,5,6-trihydroxycyclohexyl hydrogen phosphate

• ChemBase ID: 155675
• Molecular Formular: C41H90N3O19P3
• Molecular Mass: 1022.083283
• Monoisotopic Mass: 1021.53813757
• SMILES: CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)([O-])O[C@@H]1[C@@H]([C@@H]([C@H]([C@@H]([C@H]1O)OP(=O)(O)[O-])OP(=O)(O)[O-])O)O)OC(=O)CCCCCCCCCCCCCCC.[NH4+].[NH4+].[NH4+]
• 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)OP(=O)(O)[O-])OP(=O)(O)[O-])[O-].[NH4+].[NH4+].[NH4+]
• InChI: InChI=1S/C41H81O19P3.3H3N/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-34(42)55-31-33(57-35(43)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2)32-56-63(53,54)60-39-36(44)37(45)40(58-61(47,48)49)41(38(39)46)59-62(50,51)52;;;/h33,36-41,44-46H,3-32H2,1-2H3,(H,53,54)(H2,47,48,49)(H2,50,51,52);3*1H3/t33-,36-,37+,38+,39-,40-,41-;;;/m1.../s1
• InChIKey: VYFVZCYVYQYDCN-QNYQTKJTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: triammonium (1R,2R,3S,4R,5R,6S)-4-({[(2R)-2,3-bis(hexadecanoyloxy)propoxy]phosphinato}oxy)-2-(hydrogen phosphonatooxy)-3,5,6-trihydroxycyclohexyl hydrogen phosphate
• IUPAC Traditional name: triammonium (1R,2R,3S,4R,5R,6S)-4-{[(2R)-2,3-bis(hexadecanoyloxy)propoxyphosphinato]oxy}-2-(hydrogen phosphonatooxy)-3,5,6-trihydroxycyclohexyl hydrogen phosphate
• Synonyms: 1,2-Dipalmitoyl-L-α-phosphatidyl-D-myo-inositol 4,5-bisphosphate triammonium salt; L-α-Phosphatidyl-(1,2-dipalmitoyl)-D-myo-inositol 4,5-bisphosphate triammonium salt; PI(4,5)P2 (dipalmitoyl) triammonium salt; Phosphatidylinositol-4,5-diphosphate C-16 triammonium salt; PtdIns(4,5)P2 (dipalmitoyl) triammonium salt; 1,2-Dipalmitoylphosphatidylinositol 4,5-diphosphate triammonium salt

Database IDs

• PubChem SID: 24898820; 162249813
• PubChem CID: 71312197

CALCULATED PROPERTIES

• Acid pKa: 0.62676716
• H Acceptors: 13
• H Donor: 5
• LogD (pH = 5.5): 1.417185
• LogD (pH = 7.4): -1.0763382
• Log P: 8.746923
• Molar Refractivity: 228.9485 cm^3
• Polarizability: 93.836365 Å^3
• Polar Surface Area: 311.06 Å^2
• Rotatable Bonds: 42
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: solid

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%
• Shipped in: wet ice
• Linear Formula: (C41H78O19P3)-3(NH4+)3

DETAILS

Sigma Aldrich - P7115

Biochem/physiol Actions
Diphosphorylated phosphatidylinositol that may be hydrolyzed by PI-specific phospholipase C to generate IP3 and DAG.