{2-[(3-hexadecanamido-2-methoxypropyl phosphonato)oxy]ethyl}trimethylazanium hydrate

• ChemBase ID: 169905
• Molecular Formular: C25H55N2O7P
• Molecular Mass: 526.687161
• Monoisotopic Mass: 526.37468874
• SMILES: P(=O)(OCC(CNC(=O)CCCCCCCCCCCCCCC)OC)(OCC[N+](C)(C)C)[O-].O
• Canonical SMILES: CCCCCCCCCCCCCCCC(=O)NCC(COP(=O)(OCC[N+](C)(C)C)[O-])OC.O
• InChI: InChI=1S/C25H53N2O6P.H2O/c1-6-7-8-9-10-11-12-13-14-15-16-17-18-19-25(28)26-22-24(31-5)23-33-34(29,30)32-21-20-27(2,3)4;/h24H,6-23H2,1-5H3,(H-,26,28,29,30);1H2
• InChIKey: OXSZGYAIBLLMEI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {2-[(3-hexadecanamido-2-methoxypropyl phosphonato)oxy]ethyl}trimethylazanium hydrate
• IUPAC Traditional name: {2-[(3-hexadecanamido-2-methoxypropyl phosphonato)oxy]ethyl}trimethylazanium hydrate
• Synonyms: 4-Hydroxy-7-methoxy-N,N,N-trimethyl-10-oxo-3,5-dioxa-9-aza-4-phosphapentacosan-1-aminium Inner Salt 4-Oxide Hydrate; (+/-)-4-Hydroxy-7-methoxy-N,N,N-trimethyl-10-oxo-3,5-dioxa-9-aza-4-phosphapentacosan-1-aminium Inner Salt 4-Oxide Hydrate; rac-3-Hexadecanamido-2-methoxypropan-1-ol Phosphocholine Monohydrate

Database IDs

• CAS Number: 163751-35-7
• PubChem SID: 162264037
• PubChem CID: 71317217

CALCULATED PROPERTIES

• Acid pKa: 1.8610868
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 3.1302109
• LogD (pH = 7.4): 3.1303084
• Log P: 2.2088294
• Molar Refractivity: 148.9747 cm^3
• Polarizability: 55.159016 Å^3
• Polar Surface Area: 96.92 Å^2
• Rotatable Bonds: 24
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 52-60°C

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere
• Storage Warning: Hygroscopic

DETAILS

Toronto Research Chemicals - H293500

Bioactive phospholipid analogs (ether lipids, EL) of platelet activating factor (1-alkyl-2-acetyl-sn-glycero-3-phosphocholine) inhibit neoplastic cell growth in vitro and in vivo.

REFERENCES

• Noseda, A., et al.: Lipids, 22, 878 (1987)
• Marx, M.H., et al.: J. Med. Chem., 31, 858 (1988)