3-(hexadecylsulfanyl)-2-(methoxymethyl)propyl 2-(trimethylazaniumyl)ethyl phosphate

• ChemBase ID: 155782
• Molecular Formular: C26H56NO5PS
• Molecular Mass: 525.765301
• Monoisotopic Mass: 525.36168153
• SMILES: CCCCCCCCCCCCCCCCSCC(COC)COP(=O)([O-])OCC[N+](C)(C)C
• Canonical SMILES: CCCCCCCCCCCCCCCCSCC(COP(=O)(OCC[N+](C)(C)C)[O-])COC
• InChI: InChI=1S/C26H56NO5PS/c1-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22-34-25-26(23-30-5)24-32-33(28,29)31-21-20-27(2,3)4/h26H,6-25H2,1-5H3
• InChIKey: ODEDPKNSRBCSDO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(hexadecylsulfanyl)-2-(methoxymethyl)propyl 2-(trimethylazaniumyl)ethyl phosphate
• IUPAC Traditional name: ilmofosine
• Synonyms: 1-Hexadecylmercapto-2-methoxymethyl-3-propyl phosphoric acid monocholine ester; BM 41.440; Ilmofosine

Database IDs

• CAS Number: 83519-04-4
• MDL Number: MFCD00869023
• PubChem SID: 24724510; 162249920
• PubChem CID: 55008

CALCULATED PROPERTIES

• Acid pKa: 1.8766735
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 5.125656
• LogD (pH = 7.4): 5.125757
• Log P: 3.1021576
• Molar Refractivity: 158.1351 cm^3
• Polarizability: 58.82618 Å^3
• Polar Surface Area: 67.82 Å^2
• Rotatable Bonds: 26
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: soluble10 mg/mL
• Apperance: semisolid (waxy)

Safety Information

• RTECS: JH4758000
• European Hazard Symbols: Harmful (Xn)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 22
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301
• GHS Precautionary statements: P301 + P310
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• RID/ADR: UN 2811 6.1/PG 3
• Storage Temperature: -20°C

Product Information

• Empirical Formula (Hill Notation): C26H56NO5PS

DETAILS

Sigma Aldrich - I2409

Packaging
Air-sensitive, sealed under nitrogen
Biochem/physiol Actions
Protein Kinase C (PKC) inhibitor; an ether lipid derivative of lysophosphatidylcholine has antineoplastic activity in vitro and in vivo. IC50 = 560 nM. Competitive at the regulatory site of PKC. Ilmofosine is active against a variety of explanted human non-small cell lung, breast, colorectal, ovarian, renal cell cancer, and melanoma tumors in vitro at concentrations of 1-30 μg/mL.