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

• ChemBase ID: 155118
• Molecular Formular: C25H48O16P2
• Molecular Mass: 666.586542
• Monoisotopic Mass: 666.24175872
• 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)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)O)O)COC(=O)CCCCCCC
• InChI: InChI=1S/C25H48O16P2/c1-3-5-7-9-11-13-18(26)37-15-17(39-19(27)14-12-10-8-6-4-2)16-38-43(35,36)41-25-22(30)20(28)21(29)24(23(25)31)40-42(32,33)34/h17,20-25,28-31H,3-16H2,1-2H3,(H,35,36)(H2,32,33,34)/t17-,20+,21+,22-,23-,24-,25+/m1/s1
• InChIKey: LKXJHTKDXMQMDM-UCGOVMIJSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• MDL Number: MFCD02259153
• PubChem SID: 24898672; 162249256
• PubChem CID: 15432456

CALCULATED PROPERTIES

• Acid pKa: 1.0756804
• H Acceptors: 11
• H Donor: 7
• LogD (pH = 5.5): -3.0493371
• LogD (pH = 7.4): -4.201855
• Log P: 1.7573912
• Molar Refractivity: 147.8247 cm^3
• Polarizability: 60.623486 Å^3
• Polar Surface Area: 256.04 Å^2
• Rotatable Bonds: 24
• 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

Product Information

• Empirical Formula (Hill Notation): C25H48O16P2

DETAILS

Sigma Aldrich - P5578

Substrates
Component of lipid signaling pathway; formed from phosphatidylinositol by phosphatidylinositol 3-kinase.