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

• ChemBase ID: 133727
• Molecular Formular: C41H80O16P2
• Molecular Mass: 891.011822
• Monoisotopic Mass: 890.49215974
• 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)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)O)O
• InChI: InChI=1S/C41H80O16P2/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)37(45)40(39(41)47)56-58(48,49)50/h33,36-41,44-47H,3-32H2,1-2H3,(H,51,52)(H2,48,49,50)/t33-,36+,37+,38-,39-,40-,41+/m1/s1
• InChIKey: SZPQTEWIRPXBTC-KFOWTEFUSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• MDL Number: MFCD02259146
• PubChem SID: 162228004; 24898473
• PubChem CID: 643964

CALCULATED PROPERTIES

• Acid pKa: 1.0756804
• H Acceptors: 11
• H Donor: 7
• LogD (pH = 5.5): 4.0637617
• LogD (pH = 7.4): 2.9112437
• 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 - P3953

Substrates
Component of lipid signaling pathway; product of phosphatidylinositol 3-kinase.