[(2R)-2,3-bis(hexadecanoyloxy)propoxy][2-(methylamino)ethoxy]phosphinic acid

• ChemBase ID: 131844
• Molecular Formular: C38H76NO8P
• Molecular Mass: 705.985701
• Monoisotopic Mass: 705.53085503
• SMILES: CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)OCCNC)OC(=O)CCCCCCCCCCCCCCC
• Canonical SMILES: CCCCCCCCCCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCCCCCCCCCC)COP(=O)(OCCNC)O
• InChI: InChI=1S/C38H76NO8P/c1-4-6-8-10-12-14-16-18-20-22-24-26-28-30-37(40)44-34-36(35-46-48(42,43)45-33-32-39-3)47-38(41)31-29-27-25-23-21-19-17-15-13-11-9-7-5-2/h36,39H,4-35H2,1-3H3,(H,42,43)/t36-/m1/s1
• InChIKey: QSBINWBNXWAVAK-PSXMRANNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R)-2,3-bis(hexadecanoyloxy)propoxy][2-(methylamino)ethoxy]phosphinic acid
• IUPAC Traditional name: (2R)-2,3-bis(hexadecanoyloxy)propoxy(2-(methylamino)ethoxy)phosphinic acid
• Synonyms: 1,2-Dihexadecanoyl-sn-glycero-3-phospho(methylaminoethanol); 3-sn-Phosphatidyl-N-methylethanolamine,1,2-dipalmitoyl; L-α-Phosphatidylethanolamine, dipalmitoyl, N-monomethyl; L-β,γ-Dipalmitoyl-N-methyl-α-cephalin; 1,2-Dipalmitoyl-sn-glycero-3-phospho-N-methylethanolamine

Database IDs

• CAS Number: 3930-13-0
• EC Number: 223-500-2
• MDL Number: MFCD00042875
• Beilstein Number: 2198762
• PubChem SID: 162226121; 24866644
• PubChem CID: 9547031

CALCULATED PROPERTIES

• Acid pKa: 1.856178
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 10.674556
• LogD (pH = 7.4): 10.67375
• Log P: 10.674598
• Molar Refractivity: 195.7785 cm^3
• Polarizability: 78.87963 Å^3
• Polar Surface Area: 120.39 Å^2
• Rotatable Bonds: 40
• 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)
• Empirical Formula (Hill Notation): C38H76NO8P

DETAILS

Sigma Aldrich - 42558

Biochem/physiol Actions
1,2-Dipalmitoyl-sn-glycero-3-phospho-N-methylethanolamine is a N-methyl derative of phosphatidylethanolamine. 1,2-Dipalmitoyl-sn-glycero-3-phospho-N-methylethanolamine was used to study the effect of N-methylation on membrane bilayer chain melting transition, which decreases with N-methylation 1.