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

• ChemBase ID: 134115
• Molecular Formular: C25H50O22P4
• Molecular Mass: 826.546344
• Monoisotopic Mass: 826.17441976
• 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)OP(=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](OP(=O)(O)O)[C@H]([C@@H]([C@H]1O)OP(=O)(O)O)OP(=O)(O)O)O)COC(=O)CCCCCCC
• InChI: InChI=1S/C25H50O22P4/c1-3-5-7-9-11-13-18(26)41-15-17(43-19(27)14-12-10-8-6-4-2)16-42-51(39,40)47-22-20(28)23(44-48(30,31)32)25(46-50(36,37)38)24(21(22)29)45-49(33,34)35/h17,20-25,28-29H,3-16H2,1-2H3,(H,39,40)(H2,30,31,32)(H2,33,34,35)(H2,36,37,38)/t17-,20+,21+,22-,23+,24-,25-/m1/s1
• InChIKey: ANFYVAHJWGJYAT-QLCNXWICSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• MDL Number: MFCD02259165
• PubChem SID: 24898933; 162228392
• PubChem CID: 10909015

CALCULATED PROPERTIES

• Acid pKa: 0.38122156
• H Acceptors: 15
• H Donor: 9
• LogD (pH = 5.5): -8.355082
• LogD (pH = 7.4): -12.176105
• Log P: 1.5102592
• Molar Refractivity: 169.5705 cm^3
• Polarizability: 69.7504 Å^3
• Polar Surface Area: 349.1 Å^2
• Rotatable Bonds: 28
• 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 - P9953

Biochem/physiol Actions
Signaling lipid; activates PDK1 (3-phosphoinositide-dependent protein kinase), which is necessary, but not sufficient, for the activation of PKB/Akt. PDK1 also phosphorylates and activates p70S6k.