{[(2S,3R,4E)-2-amino-3-hydroxy(1,2-13C2,1,1-2H2)octadec-4-en-1-yl]oxy}phosphonic acid

• ChemBase ID: 177837
• Molecular Formular: C18H38NO5P
• Molecular Mass: 381.45709068
• Monoisotopic Mass: 381.25546963
• SMILES: O([13CH2][13C@H]([C@@H](/C=C/CCCCCCCCCCCCC)O)N)P(=O)(O)O
• Canonical SMILES: CCCCCCCCCCCCC/C=C/[C@H]([13C@@H]([13CH2]OP(=O)(O)O)N)O
• InChI: InChI=1S/C18H38NO5P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(20)17(19)16-24-25(21,22)23/h14-15,17-18,20H,2-13,16,19H2,1H3,(H2,21,22,23)/b15-14+/t17-,18-/m1/s1/i16+1,17+1
• InChIKey: DUYSYHSSBDVJSM-WCGBYYEMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(2S,3R,4E)-2-amino-3-hydroxy(1,2-^1^3C₂,1,1-^2H₂)octadec-4-en-1-yl]oxy}phosphonic acid
• IUPAC Traditional name: [(2S,3R,4E)-2-amino-3-hydroxy(1,2-^1^3C₂,1,1-^2H₂)octadec-4-en-1-yl]oxyphosphonic acid
• Synonyms: D-erythro-Sphingosine-1-phosphate-13C2,D2

Database IDs

• PubChem SID: 164233747
• PubChem CID: 71752222

CALCULATED PROPERTIES

• Acid pKa: 1.510148
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): 3.3954642
• LogD (pH = 7.4): 2.525948
• Log P: 3.4308577
• Molar Refractivity: 102.7649 cm^3
• Polarizability: 40.662235 Å^3
• Polar Surface Area: 113.01 Å^2
• Rotatable Bonds: 17
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Warm Acetic Acid
• Apperance: White to Off-White Solid
• Melting Point: >158°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer
• Storage Warning: Moisture, Temperature Sensitive; Hygroscopic

DETAILS

Toronto Research Chemicals - S681502

A labelled putative lipid second messenger; found to inhibit cellular mobility of melanoma cells at very low concentrations with no toxic effects thereby making it a possible agent for prevention of tumor cell metastasis and inflammatory processes; mobi

REFERENCES

• Zhang, H., et al.: J. Cell Biol., 114, 155 (1991) Sadahira, Y., et al.: Proc. Natl. Acad. Sci. USA (1992)
• Cuvillier, O., et al.: Nature, 381, 800 (1996)