 Chemical Structure.png)
Physicochemical Properties
| Molecular Formula | C18H40NO5P |
| Molecular Weight | 381.49 |
| Exact Mass | 381.264 |
| CAS # | 19794-97-9 |
| Related CAS # | Sphinganine 1-phosphate-d7;2315262-23-6 |
| PubChem CID | 644260 |
| Appearance | White to off-white solid powder |
| Vapour Pressure | 2.66E-14mmHg at 25°C |
| LogP | 4.965 |
| Hydrogen Bond Donor Count | 4 |
| Hydrogen Bond Acceptor Count | 6 |
| Rotatable Bond Count | 18 |
| Heavy Atom Count | 25 |
| Complexity | 337 |
| Defined Atom Stereocenter Count | 2 |
| SMILES | CCCCCCCCCCCCCCC[C@H]([C@H](COP(=O)(O)O)N)O |
| InChi Key | YHEDRJPUIRMZMP-ZWKOTPCHSA-N |
| InChi Code | InChI=1S/C18H40NO5P/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/h17-18,20H,2-16,19H2,1H3,(H2,21,22,23)/t17-,18+/m0/s1 |
| Chemical Name | [(2S,3R)-2-amino-3-hydroxyoctadecyl] dihydrogen phosphate |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| Targets | Human Endogenous Metabolite |
| ln Vitro | Sphinganine 1-phosphate (S1P) is a powerful signaling molecule implicated in angiogenesis, cancer, lymphocyte trafficking, and cell stress responses. The main way that sphinganine 1-phosphate works is by stimulating a particular subset of G-protein coupled cell surface receptors called the endothelial differentiation gene (EDG) family. Sphinganine 1-phosphate regulates cell metabolism in the opposite way. Skeletal muscle regeneration and differentiation are regulated by sphinganine 1-phosphate[1]. In cancer, sphinganine 1-phosphate (S1P) plays a role. Sphinganine 1-phosphate controls a number of biological processes, including neovascularization, which gives cancer cells oxygen and nutrition, development, and survival of cells, and inflammation, which can promote tumorigenesis[1]. Human renal endothelial cells are stimulated to produce HSP27 and phosphorylated ERK MAPK, Akt, and HSP27 by Sphinganine-1-Phosphate (1 μM)[2]. |
| ln Vivo | In diabetic mice, sphinganine 1-phosphate can improve wound healing[1]. After liver ischemia and reperfusion (IR) injury in rats, sphinganine 1-phosphate protects the kidneys and liver by selectively activating S1P1 receptors and pertussis toxin-sensitive G-proteins, which in turn activates ERK and Akt. After liver IR, sphinganine 1-phosphate (0.1 mg/kg iv just before reperfusion and 0.2 mg/kg sc two hours later) guards against hepatic and renal damage[2]. |
| Cell Assay |
Cell Viability Assay[2] Cell Types: Human renal endothelial cells or human kidney proximal tubule (HK-2) cells Tested Concentrations: 1 μM Incubation Duration: 2 or 4 hrs (hours) Experimental Results: Induced HSP27 mRNA in cultured human renal endothelial cells. Phosphorylated ERK MAPK and AKT in human renal endothelial cells in a time-dependent manner. Phosphorylated and induced HSP27. |
| Animal Protocol |
Animal/Disease Models: Male C57BL /6 mice (20-25 g)[2] Doses: 0.1 mg/kg Route of Administration: Administered iv immediately before reperfusion and 0.2 mg/kg sc 2 h after reperfusion Experimental Results: The plasma level of alanine aminotransferase (ALT) and Creatinine (Cr ) was 80±6 U/L and 0.46±0.05 mg/dL, respectively. The increases in ALT (7474±557 U/L) and Cr (0.55±0.05 mg/dL) were Dramatically suppressed at 24 h after reperfusion in mice treated with 0.1 mg/kg iv before reperfusion and 0.2 mg/kg sc 2 h after reperfusion. |
| References |
[1]. Sphingosine 1-phosphate lyase, a key regulator of sphingosine 1-phosphate signaling and function. Adv Enzyme Regul. 2010;50(1):349-62. [2]. Sphinganine-1-phosphate protects kidney and liver after hepatic ischemia and reperfusion in mice through S1P1 receptor activation. Lab Invest. 2010 Aug;90(8):1209-24. |
| Additional Infomation |
Sphinganine 1-phosphate is a sphingoid 1-phosphate that is the monophosphorylated derivative of sphinganine. It has a role as a mouse metabolite. It is functionally related to a sphinganine. It is a conjugate acid of a sphinganine 1-phosphate(1-). Sphinganine 1-phosphate has been reported in Homo sapiens with data available. |
Solubility Data
| Solubility (In Vitro) | May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples |
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] *Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.6213 mL | 13.1065 mL | 26.2130 mL | |
| 5 mM | 0.5243 mL | 2.6213 mL | 5.2426 mL | |
| 10 mM | 0.2621 mL | 1.3107 mL | 2.6213 mL |