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

• ChemBase ID: 153307
• Molecular Formular: C41H81O19P3
• Molecular Mass: 970.991723
• Monoisotopic Mass: 970.45849026
• 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
• 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
• InChI: InChI=1S/C41H81O19P3/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)/t33-,36-,37-,38+,39+,40+,41+/m1/s1
• InChIKey: HKWJHKSHEWVOSS-OMDJCSNQSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• MDL Number: MFCD01861926
• PubChem SID: 162247446
• PubChem CID: 643960

CALCULATED PROPERTIES

• H Acceptors: 13
• H Donor: 8
• LogD (pH = 5.5): 1.417185
• LogD (pH = 7.4): -1.0763382
• Log P: 8.746923
• Molar Refractivity: 232.3136 cm^3
• Polarizability: 94.182274 Å^3
• Polar Surface Area: 302.57 Å^2
• Rotatable Bonds: 42
• Lipinski's Rule of Five: false
• Acid pKa: 0.62676716

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

Product Information

• Empirical Formula (Hill Notation): C41H81O19P3

DETAILS

Sigma Aldrich - P1225

Biochem/physiol Actions
Activates Ca2+-insensitive PKC isotypes δ, ε, and η; activates Akt (a serine-threonine kinase also known as PKBα) by direct interaction with the Akt pleckstrin homology domain.