(2-{[(2S)-2,3-bis(hexadecanoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium

• ChemBase ID: 155859
• Molecular Formular: C40H80NO8P
• Molecular Mass: 734.038861
• Monoisotopic Mass: 733.56215516
• SMILES: CCCCCCCCCCCCCCCC(=O)OC[C@@H](COP(=O)([O-])OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCC
• Canonical SMILES: CCCCCCCCCCCCCCCC(=O)OC[C@H](OC(=O)CCCCCCCCCCCCCCC)COP(=O)(OCC[N+](C)(C)C)[O-]
• InChI: InChI=1S/C40H80NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-39(42)46-36-38(37-48-50(44,45)47-35-34-41(3,4)5)49-40(43)33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h38H,6-37H2,1-5H3/t38-/m0/s1
• InChIKey: KILNVBDSWZSGLL-LHEWISCISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2-{[(2S)-2,3-bis(hexadecanoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium
• IUPAC Traditional name: (2-{[(2S)-2,3-bis(hexadecanoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium
• Synonyms: 1-sn-Phosphatidylcholine, 2,3-dipalmitoyl; D-β,γ-Dipalmitoyl-α-lecithin; 2,3-Dipalmitoyl-sn-glycero-1-phosphocholine

Database IDs

• CAS Number: 35418-55-4
• MDL Number: MFCD00070354
• Beilstein Number: 5787775
• PubChem SID: 162249997; 24866654
• PubChem CID: 3032281

CALCULATED PROPERTIES

• Acid pKa: 1.8550572
• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 10.1373005
• LogD (pH = 7.4): 10.137397
• Log P: 8.113796
• Molar Refractivity: 215.8651 cm^3
• Polarizability: 82.38789 Å^3
• Polar Surface Area: 111.19 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: ≥95.0% (TLC)
• Empirical Formula (Hill Notation): C40H80NO8P

DETAILS

Sigma Aldrich - 42566

Biochem/physiol Actions
2,3-Dipalmitoyl-sn-glycerol-1-phosphocholine is a major constituent of lung surfactant, a monolayer reducing lung surface tension and keeping the lung from collapsing when exhaling 1.