(2-{[(2R)-3-(hexadecanoyloxy)-2-hydroxypropyl phosphonato]oxy}ethyl)trimethylazanium

• ChemBase ID: 132986
• Molecular Formular: C24H50NO7P
• Molecular Mass: 495.630061
• Monoisotopic Mass: 495.33248958
• SMILES: CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)([O-])OCC[N+](C)(C)C)O
• Canonical SMILES: CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(OCC[N+](C)(C)C)[O-])O
• InChI: InChI=1S/C24H50NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-24(27)30-21-23(26)22-32-33(28,29)31-20-19-25(2,3)4/h23,26H,5-22H2,1-4H3/t23-/m1/s1
• InChIKey: ASWBNKHCZGQVJV-HSZRJFAPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2-{[(2R)-3-(hexadecanoyloxy)-2-hydroxypropyl phosphonato]oxy}ethyl)trimethylazanium
• IUPAC Traditional name: (2-{[(2R)-3-(hexadecanoyloxy)-2-hydroxypropyl phosphonato]oxy}ethyl)trimethylazanium
• Synonyms: 1-Hexadecanoyl-sn-glycero-3-phosphocholine; 3-sn-Lysophosphatidylcholine, 1-palmitoyl; L-α-Palmitoyl-lysophosphatidylcholine; L-γ-Palmitoyl-α-lysolecithin; Lysolecithin, palmitoyl; 1-Palmitoyl-sn-glycero-3-phosphocholine; (7R)-3,5,9-4,7-Dihydroxy-N,N,N-trimethyl-10-oxotrioxa-4-phosphapentacosan-1-aminium 4-Oxide Inner Salt; 1-Hexadecanoyl-sn-glycerol-3-phosphorylcholine; 1-Hexadecanoyllysolecithin; 1-O-Palmitoyl-2-lyso-sn-glycero-3-phosphocholine; MPPC; Palmitoyl L-Lysophosphatidylcholine; Palmitoyl L-α-Lysolecithin; Palmitoyl L-α-Lysophosphatidylcholine; γ-Palmitoyl-L-α-lysophosphatidylcholine; 1-Palmitoyl-sn-glycero-3-phosphocholine

Database IDs

• CAS Number: 17364-16-8
• MDL Number: MFCD00036904
• Beilstein Number: 5385682
• PubChem SID: 24896398; 162227263
• PubChem CID: 460602

CALCULATED PROPERTIES

• Acid pKa: 1.8553406
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 3.2162461
• LogD (pH = 7.4): 3.2163422
• Log P: 1.1927425
• Molar Refractivity: 142.2737 cm^3
• Polarizability: 52.821243 Å^3
• Polar Surface Area: 105.12 Å^2
• Rotatable Bonds: 24
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: White Solid
• Melting Point: >192°C (dec.)

Safety Information

• Storage Condition: Refrigerator
• 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%
• Biological Source: synthetic

DETAILS

Toronto Research Chemicals - P157345

A lipid biomarker for stable and unstable heart disease.

REFERENCES

• Gaziano, J., et al.: Circulation, 96, 2520 (1997)
• Thomas, A., et al.: Anal. Chem., 82, 6687 (1997)