{[(1R,2S,3R,4R,5R,6R)-4-({[(2R)-2,3-bis(hexadecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)-2,3,5,6-tetrahydroxycyclohexyl]oxy}phosphonic acid amine

• ChemBase ID: 132929
• Molecular Formular: C41H83NO16P2
• Molecular Mass: 908.042342
• Monoisotopic Mass: 907.51870884
• 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)OP(=O)(O)O)O)O)OC(=O)CCCCCCCCCCCCCCC.N
• 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)OP(=O)(O)O)O.N
• InChI: InChI=1S/C41H80O16P2.H3N/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-34(42)53-31-33(55-35(43)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2)32-54-59(51,52)57-41-38(46)36(44)40(37(45)39(41)47)56-58(48,49)50;/h33,36-41,44-47H,3-32H2,1-2H3,(H,51,52)(H2,48,49,50);1H3/t33-,36-,37+,38-,39-,40+,41+;/m1./s1
• InChIKey: LVICQWVAYMJTST-LCJGNHTMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(1R,2S,3R,4R,5R,6R)-4-({[(2R)-2,3-bis(hexadecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)-2,3,5,6-tetrahydroxycyclohexyl]oxy}phosphonic acid amine
• IUPAC Traditional name: [(1R,2S,3R,4R,5R,6R)-4-{[(2R)-2,3-bis(hexadecanoyloxy)propoxy(hydroxy)phosphoryl]oxy}-2,3,5,6-tetrahydroxycyclohexyl]oxyphosphonic acid amine
• Synonyms: L-α-Phosphatidyl-D-myo-inositol 4-monophosphate, dipalmitoyl ammonium salt

Database IDs

• MDL Number: MFCD12910458
• PubChem SID: 162227206; 24898867
• PubChem CID: 71308610

CALCULATED PROPERTIES

• Acid pKa: 1.078359
• H Acceptors: 11
• H Donor: 7
• LogD (pH = 5.5): 4.064341
• LogD (pH = 7.4): 2.9140902
• Log P: 8.87049
• Molar Refractivity: 221.4407 cm^3
• Polarizability: 89.7429 Å^3
• Polar Surface Area: 256.04 Å^2
• Rotatable Bonds: 40
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: chloroform: soluble; DMSO: soluble; ethanol: 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

DETAILS

Sigma Aldrich - P7686

Substrates
Component of lipid signaling pathway; substrate for phosphatidylinositol 3-kinase and phosphatidylinositol-4-phosphate 5-kinase; shown to promote β-adrenergic receptor kinase phosphorylation of the β2-adrenergic receptor.