(2-{[(2R)-2,3-bis(icosa-5,8,11,14,17-pentaenoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium

• ChemBase ID: 154516
• Molecular Formular: C48H76NO8P
• Molecular Mass: 826.092701
• Monoisotopic Mass: 825.53085503
• SMILES: CC/C=C/C/C=C/C/C=C/C/C=C/C/C=C/CCCC(=O)OC[C@H](COP(=O)([O-])OCC[N+](C)(C)C)OC(=O)CCC/C=C/C/C=C/C/C=C/C/C=C/C/C=C/CC
• Canonical SMILES: CC/C=C/C/C=C/C/C=C/C/C=C/C/C=C/CCCC(=O)OC[C@@H](OC(=O)CCC/C=C/C/C=C/C/C=C/C/C=C/C/C=C/CC)COP(=O)(OCC[N+](C)(C)C)[O-]
• InChI: InChI=1S/C48H76NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-38-40-47(50)54-44-46(45-56-58(52,53)55-43-42-49(3,4)5)57-48(51)41-39-37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h8-11,14-17,20-23,26-29,32-35,46H,6-7,12-13,18-19,24-25,30-31,36-45H2,1-5H3/t46-/m1/s1
• InChIKey: WAIHGVAZVKEQGR-YACUFSJGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2-{[(2R)-2,3-bis(icosa-5,8,11,14,17-pentaenoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium
• IUPAC Traditional name: (2-{[(2R)-2,3-bis(icosa-5,8,11,14,17-pentaenoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium
• Synonyms: 1,2-Di-(5Z,8Z,11Z,14Z,17Z-eicosapentaenoyl)-sn-glycero-3-phosphocholine; EPAPC; PC(20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)); 1,2-Dieicosapentaenoyl-sn-glycero-3-phosphocholine

Database IDs

• CAS Number: 99296-78-3
• PubChem SID: 162248655
• PubChem CID: 71311886

CALCULATED PROPERTIES

• Acid pKa: 1.8550572
• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 10.074633
• LogD (pH = 7.4): 10.074729
• Log P: 8.051129
• Molar Refractivity: 263.8391 cm^3
• Polarizability: 94.70917 Å^3
• Polar Surface Area: 111.19 Å^2
• Rotatable Bonds: 38
• Lipinski's Rule of Five: false

PROPERTIES

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

• Purity: ≥99.0% (TLC)
• Biological Source: from synthetic
• Empirical Formula (Hill Notation): C48H76NO8P

DETAILS

Sigma Aldrich - 40723

General description
Though unusual in higher animals, di-polyunsaturated-fatty-acid phosphatidylcholine (diPUFA-PtdCho) is produced at high abundance by the roundworm Caenorhabditis elegans, especially when grown at below normal temperature. C. elegans acyltransferase is unusual in exhibiting no preference for saturated over unsaturated fatty acids.1