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Activity Type | Activity Value -log(M) | Mechanism of Action | Activity Reference | Publications (PubMed IDs) |
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SKU | Size | Availability | Price | Qty |
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D130606-1mg | 1mg | Available within 4-8 weeks(?) Items will be manufactured post-order and can take 4-8 weeks. Thank you for your patience! | $232.90 | |
D130606-5mg | 5mg | Available within 4-8 weeks(?) Items will be manufactured post-order and can take 4-8 weeks. Thank you for your patience! | $513.90 |
Endogenous signaling sphingolipid and agonist of S1P receptors
Synonyms | (2S,3R,4E)-2-amino-3-hydroxyoctadec-4-en-1-yl dihydrogen phosphate | 4-Octadecene-1,3-diol, 2-amino-, 1-(dihydrogen phosphate), (2S,3R,4E)- | 4-Octadecene-1,3-diol, 2-amino-, 1-(dihydrogen phosphate), (R-(R*,S*-(E)))- | Sphingosine 1-phosphate, >=95%, pow |
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Specifications & Purity | Moligand™, ≥98% |
Biochemical and Physiological Mechanisms | 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. I |
Storage Temp | Store at -20°C,Argon charged |
Shipped In | Ice chest + Ice pads |
Grade | Moligand™ |
Action Type | AGONIST |
Mechanism of action | Agonist of GPR12;Agonist of GPR3;Agonist of GPR63;Agonist of GPR6;Agonist of P2RY10;Agonist of S1P 1 receptor;Agonist of S1P 2 receptor;Agonist of S1P 3 receptor;Agonist of S1P 4 receptor;Agonist of S1P 5 receptor |
Note | Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. For delivery of sphingosine-1-phosphate to cells, prepare a 125μM stock in 4mg/ml BSA as follows: Dissolve sphingosine-1-phosphate (S-1-P) in methanol (0.5 mg/ml). This may require boiling (65°C), with occasional replacement of evaporated methanol. Crushing of solid prior to addition of methanol and crushing and stirring during heating is helpful. Aliquot desired amounts of methanol stock to tubes. Evaporate the solvent with a stream of nitrogen, swirling to deposit a thin film on the inside of the tube. Aliquots may be stored at -20 °C at this point or dissolved with enough 4mg/ml BSA (fatty acid free Bovine Serum Albumin in water; 37°C, 30 min. with repeated vortexing) to make 125 µM stock. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details. |
Product Description | D-erythro-Sphingosine-1-phosphate(S1P) is a polar sphingolipid metabolite which regulates diverse cellular responses including cell growth, survival and migration. S1P was reported to stimulate DNA synthesis and cell division in quiescent cultures of Swiss 3T3 fibroblasts and to trigger the dual signal transduction pathways of calcium mobilization and PC-PLD (phospholipase D) activation. S1P serves as a second messenger for intracellular calcium mobilization in U-937 cells and decreases cellular cAMP. Recent studies show that S1P is a G-protein-coupled receptor (GPCR) ligand for the EDG-1 family, including EDG-1, -3, -5, -6 and -8. This bioactive lipid mediator has been shown to stimulate the ERK pathway and to also counteract the ceramide-induced activation of stress-activated protein kinase (SAPK/JNK). Researchers have also found that S1P is a strong inhibitor of cell motility and phagokinesis in B16 melanoma cells. Additionally, it induces rapid and transient tyrosine phosphorylation of epidermal growth factor receptor (EGFR) and c-Met in gastric cancer cells. S1P has also been known as a tumor-promoting lipid. Suggested to be an activator of GPR3, GPR6, and GPR12. D-erythro-Sphingosine-1-phosphate is an activator of EDG-1, EDG-3, EDG-2, EDG-4 and EDG-5. |
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IUPAC Name | [(E,2S,3R)-2-amino-3-hydroxyoctadec-4-enyl] dihydrogen phosphate |
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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+/m0/s1 |
InChi Key | DUYSYHSSBDVJSM-KRWOKUGFSA-N |
Canonical SMILES | CCCCCCCCCCCCCC=CC(C(COP(=O)(O)O)N)O |
Isomeric SMILES | CCCCCCCCCCCCC/C=C/[C@H]([C@H](COP(=O)(O)O)N)O |
WGK Germany | 3 |
PubChem CID | 5283560 |
Molecular Weight | 379.472 |
PubChem CID | 5283560 |
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ChEBI | CHEBI:37550 |
Wikipedia | Sphingosine-1-phosphate |
BindingDB Ligand | 50158348 |
ChEMBL Ligand | CHEMBL225155 |
CAS Registry No. | 26993-30-6 |
RCSB PDB Ligand | S1P |
GPCRdb Ligand | sphingosine 1-phosphate |
Enter Lot Number to search for COA:
Find and download the COA for your product by matching the lot number on the packaging.
Lot Number | Certificate Type | Date | Item |
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K2229376 | Certificate of Analysis | Nov 23, 2022 | D130606 |
K2229502 | Certificate of Analysis | Nov 23, 2022 | D130606 |
H2205076 | Certificate of Analysis | Jul 21, 2022 | D130606 |
H2205077 | Certificate of Analysis | Jul 21, 2022 | D130606 |
C2228024 | Certificate of Analysis | Mar 01, 2022 | D130606 |
C2228035 | Certificate of Analysis | Mar 01, 2022 | D130606 |
Solubility | Soluble in warm acetic acid, 0.3M NaOH (~4 mg/ml), and methanol: THF: water (6:3:1) (>0.5 mg/ml). Insoluble in water. |
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Sensitivity | Moisture & Light & Air sensitive |
Melt Point(°C) | 179-189°C |
Pictogram(s) | GHS07 |
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Signal | Warning |
Hazard Statements | H315:Causes skin irritation H319:Causes serious eye irritation H335:May cause respiratory irritation |
Precautionary Statements | P261:Avoid breathing dust/fume/gas/mist/vapors/spray. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present and easy to do - continue rinsing. P280:Wear protective gloves/protective clothing/eye protection/face protection. P302+P352:IF ON SKIN: wash with plenty of water. P321:Specific treatment (see ... on this label). P405:Store locked up. P501:Dispose of contents/container to ... P264:Wash hands [and …] thoroughly after handling. P271:Use only outdoors or in a well-ventilated area. P304+P340:IF INHALED: Remove person to fresh air and keep comfortable for breathing. P403+P233:Store in a well-ventilated place. Keep container tightly closed. P362+P364:Take off contaminated clothing and wash it before reuse. P264+P265:Wash hands [and …] thoroughly after handling. Do not touch eyes. P337+P317:If eye irritation persists: Get medical help. P332+P317:If skin irritation occurs: Get medical help. P319:Get medical help if you feel unwell. |
WGK Germany | 3 |
1. Xiaomei Wu, Bin Pang, Jianwei You, Leiye Yu, Ruobing Ren, Hongyang Wang, Li Chen. (2023) An LC-MS-based workflow measures the export activity of S1P transporters. BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 668 (118). [PMID:37245292] |
2. Xinhua Liu, Youteng Qin, Liyun Dong, Ziyi Han, Tianning Liu, Ying Tang, Yun Yu, Jingjie Ye, Juan Tao, Xuan Zeng, Jun Feng, Xian-Zheng Zhang. (2023) Living symbiotic bacteria-involved skin dressing to combat indigenous pathogens for microbiome-based biotherapy toward atopic dermatitis. Bioactive Materials, 21 (253). [PMID:36157249] |
1. Xiaomei Wu, Bin Pang, Jianwei You, Leiye Yu, Ruobing Ren, Hongyang Wang, Li Chen. (2023) An LC-MS-based workflow measures the export activity of S1P transporters. BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 668 (118). [PMID:37245292] |
2. Xinhua Liu, Youteng Qin, Liyun Dong, Ziyi Han, Tianning Liu, Ying Tang, Yun Yu, Jingjie Ye, Juan Tao, Xuan Zeng, Jun Feng, Xian-Zheng Zhang. (2023) Living symbiotic bacteria-involved skin dressing to combat indigenous pathogens for microbiome-based biotherapy toward atopic dermatitis. Bioactive Materials, 21 (253). [PMID:36157249] |