{[(1R,2R,3S,4R,5R,6S)-4-({[(2R)-2,3-bis(octanoyloxy)propoxy](hydroxy)phosphoryl}oxy)-3,5,6-trihydroxy-2-(phosphonooxy)cyclohexyl]oxy}phosphonic acid

• ChemBase ID: 133302
• Molecular Formular: C25H49O19P3
• Molecular Mass: 746.566443
• Monoisotopic Mass: 746.20808924
• SMILES: CCCCCCCC(=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)CCCCCCC
• Canonical SMILES: CCCCCCCC(=O)O[C@@H](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)COC(=O)CCCCCCC
• InChI: InChI=1S/C25H49O19P3/c1-3-5-7-9-11-13-18(26)39-15-17(41-19(27)14-12-10-8-6-4-2)16-40-47(37,38)44-23-20(28)21(29)24(42-45(31,32)33)25(22(23)30)43-46(34,35)36/h17,20-25,28-30H,3-16H2,1-2H3,(H,37,38)(H2,31,32,33)(H2,34,35,36)/t17-,20-,21+,22+,23-,24-,25-/m1/s1
• InChIKey: XLNCEHRXXWQMPK-MJUMVPIBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(1R,2R,3S,4R,5R,6S)-4-({[(2R)-2,3-bis(octanoyloxy)propoxy](hydroxy)phosphoryl}oxy)-3,5,6-trihydroxy-2-(phosphonooxy)cyclohexyl]oxy}phosphonic acid
• IUPAC Traditional name: [(1R,2R,3S,4R,5R,6S)-4-{[(2R)-2,3-bis(octanoyloxy)propoxy(hydroxy)phosphoryl]oxy}-3,5,6-trihydroxy-2-(phosphonooxy)cyclohexyl]oxyphosphonic acid
• Synonyms: L-α-Phosphatidyl-D-myo-inositol 4,5-diphosphate, dioctanoyl

Database IDs

• MDL Number: MFCD02259161
• PubChem SID: 162227579; 24898428
• PubChem CID: 9543520

CALCULATED PROPERTIES

• Acid pKa: 0.62676716
• H Acceptors: 13
• H Donor: 8
• LogD (pH = 5.5): -5.695914
• LogD (pH = 7.4): -8.189437
• Log P: 1.6338252
• Molar Refractivity: 158.6976 cm^3
• Polarizability: 65.17116 Å^3
• Polar Surface Area: 302.57 Å^2
• Rotatable Bonds: 26
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: 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 - P3584

Substrates
Signaling lipid which apparently acts by binding to pleckstrin homology domains; direct activator of inward rectifier potassium channels; phospholipase C and PI3-kinase substrate; activates phospholipase D.