{[(4E)-3-hydroxy-2-octanamidooctadec-4-en-1-yl]oxy}phosphonic acid

• ChemBase ID: 163990
• Molecular Formular: C26H52NO6P
• Molecular Mass: 505.667941
• Monoisotopic Mass: 505.35322502
• SMILES: CCCCCCCCCCCCC/C=C/C(C(COP(=O)(O)O)NC(=O)CCCCCCC)O
• Canonical SMILES: CCCCCCCCCCCCC/C=C/C(C(NC(=O)CCCCCCC)COP(=O)(O)O)O
• InChI: InChI=1S/C26H52NO6P/c1-3-5-7-9-10-11-12-13-14-15-16-18-19-21-25(28)24(23-33-34(30,31)32)27-26(29)22-20-17-8-6-4-2/h19,21,24-25,28H,3-18,20,22-23H2,1-2H3,(H,27,29)(H2,30,31,32)/b21-19+
• InChIKey: VSSNYUXSRXINIP-XUTLUUPISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(4E)-3-hydroxy-2-octanamidooctadec-4-en-1-yl]oxy}phosphonic acid
• IUPAC Traditional name: [(4E)-3-hydroxy-2-octanamidooctadec-4-en-1-yl]oxyphosphonic acid
• Synonyms: N-[2-Hydroxy-1-[(phosphonooxy)methyl]-3-heptadecen-1-yl]octanamide; N-Octanoylsphingosine-1-phosphate; C8 Ceramide-1-phosphate

Database IDs

• CAS Number: 887353-95-9
• PubChem SID: 162258125
• PubChem CID: 6384103

CALCULATED PROPERTIES

• Acid pKa: 1.528374
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): 4.781171
• LogD (pH = 7.4): 3.902242
• Log P: 7.0234156
• Molar Refractivity: 139.8406 cm^3
• Polarizability: 55.07053 Å^3
• Polar Surface Area: 116.09 Å^2
• Rotatable Bonds: 24
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Methanol
• Apperance: White Crystalline Solid
• Melting Point: 138-140°C

DETAILS

Toronto Research Chemicals - C262720

Stimulates DNA synthesis when added exogenously to cultured fibroblasts at 5μM. Mitogenic activity is antagonized by cell permeable ceramides.

REFERENCES

• Gomez-Munoz, A., et al.: Mol. Pharmacol., 47, 883 (1995)