{[(2S,3R)-2-amino-3-hydroxyoctadec-4-en-1-yl]oxy}phosphonic acid

• ChemBase ID: 129593
• Molecular Formular: C18H38NO5P
• Molecular Mass: 379.471781
• Monoisotopic Mass: 379.24875995
• SMILES: O=P(O)(OC[C@H](N)[C@H](O)/C=C/CCCCCCCCCCCCC)O
• Canonical SMILES: CCCCCCCCCCCCC/C=C/[C@H]([C@H](COP(=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)/t17-,18+/m0/s1
• InChIKey: DUYSYHSSBDVJSM-ZWKOTPCHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(2S,3R)-2-amino-3-hydroxyoctadec-4-en-1-yl]oxy}phosphonic acid; {[(2S,3R,4E)-2-amino-3-hydroxyoctadec-4-en-1-yl]oxy}phosphonic acid
• IUPAC Traditional name: [(2S,3R)-2-amino-3-hydroxyoctadec-4-en-1-yl]oxyphosphonic acid; sphingosine 1-phosphate
• Synonyms: Sphingosine-1-phosphate; (2S,3R,4E)-2-Amino-4-octadecene-1,3-diol 1-phosphate; D-erythro-Sphingosine 1-phosphate; Sphingosine 1-phosphate; (2S,3R,4E)-2-Amino-4-octadecene-1,3-diol 1-(Dihydrogen phosphate); Sphingosine-1-phosphate; SPN-1-P; S1P.; D-erythro-Sphingosine-1-phosphate

Database IDs

• CAS Number: 26993-30-6
• MDL Number: MFCD00270077
• PubChem SID: 24899853; 162223883
• PubChem CID: 5283560
• CHEBI ID: 37550
• CHEMBL: 225155
• Chemspider ID: 4446673
• IUPHAR ligand ID: 911
• KEGG ID: C06124
• MeSH Name: sphingosine+1-phosphate
• Wikipedia Title: Sphingosine-1-phosphate

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: Off-White to Grey Powder; powder
• Melting Point: 179-189°C

Safety Information

• Storage Condition: -20°C Freezer
• Storage Warning: Moisture, Temperature Sensitive; Hygroscopic
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: human ... S1PR1(1901), S1PR2(9294), S1PR3(1903), S1PR4(8698), S1PR5(53637)

Product Information

• Purity: ≥95%
• Quality Level: PREMIUM

DETAILS

Sigma Aldrich - S9666

Biochem/physiol Actions
A lipid second messenger that binds to S1P1 and S1P3 receptors. Mobilizes intracellular Ca2+ stores and decreases cellular cAMP. Activates phospholipase D. S1P stimulates the migration of endothelial cells but inhibits the migration of other cell types. Induces angiogenesis.

Toronto Research Chemicals - S681500

A 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; mobilizes int

REFERENCES

• Yeh, C., et al.: Am. J. Physiol., 296, H1193 (2009)
• Hagen, N., et al.: J. Biol. Chem., 284, 11346 (2009)
• Kuehnel, M., et al.: J. Cell Sci., 122, 499 (2009)