D-erythro-sphingosine-1-phosphate - ≥98.0%, high purity , CAS No.26993-30-6, 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

2 Citations
Item Number
D130606
Grouped product items
SKUSizeAvailabilityPrice Qty
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

Basic Description

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
Specifications & PurityMoligand™, ≥98%
Biochemical and Physiological MechanismsA 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 TempStore at -20°C,Argon charged
Shipped InIce chest + Ice pads
GradeMoligand™
Action TypeAGONIST
Mechanism of actionAgonist 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
NoteWherever 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.
A ligand for EDG-1 and EDG-3 and activator of GPR3, GPR6, and GPR12.

Associated Targets(Human)

GPR12 Tbio G-protein coupled receptor 12 (0 Activities)
Activity TypeActivity Value -log(M)Mechanism of ActionActivity ReferencePublications (PubMed IDs)
GPR3 Tchem G-protein coupled receptor 3 (0 Activities)
Activity TypeActivity Value -log(M)Mechanism of ActionActivity ReferencePublications (PubMed IDs)
GPR63 Tchem Probable G-protein coupled receptor 63 (0 Activities)
Activity TypeActivity Value -log(M)Mechanism of ActionActivity ReferencePublications (PubMed IDs)
GPR6 Tchem G-protein coupled receptor 6 (0 Activities)
Activity TypeActivity Value -log(M)Mechanism of ActionActivity ReferencePublications (PubMed IDs)
S1PR5 Tclin Sphingosine 1-phosphate receptor 5 (12 Activities)
Activity TypeActivity Value -log(M)Mechanism of ActionActivity ReferencePublications (PubMed IDs)
S1PR2 Tchem Sphingosine 1-phosphate receptor 2 (11 Activities)
Activity TypeActivity Value -log(M)Mechanism of ActionActivity ReferencePublications (PubMed IDs)
S1PR4 Tclin Sphingosine 1-phosphate receptor 4 (9 Activities)
Activity TypeActivity Value -log(M)Mechanism of ActionActivity ReferencePublications (PubMed IDs)
S1PR1 Tclin Sphingosine 1-phosphate receptor 1 (21 Activities)
Activity TypeActivity Value -log(M)Mechanism of ActionActivity ReferencePublications (PubMed IDs)
S1PR3 Tclin Sphingosine 1-phosphate receptor 3 (19 Activities)
Activity TypeActivity Value -log(M)Mechanism of ActionActivity ReferencePublications (PubMed IDs)
P2RY10 Tchem Putative P2Y purinoceptor 10 (1 Activities)
Activity TypeActivity Value -log(M)Mechanism of ActionActivity ReferencePublications (PubMed IDs)
ABL1 Tclin Tyrosine-protein kinase ABL (18331 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADRB2 Tclin Beta-2 adrenergic receptor (11824 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADRA2A Tclin Alpha-2a adrenergic receptor (9450 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
AGTR1 Tclin Type-1 angiotensin II receptor (5176 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GSK3B Tclin Glycogen synthase kinase-3 beta (11785 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CSNK1D Tchem Casein kinase I delta (4546 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
S1PR4 Tclin Sphingosine 1-phosphate receptor Edg-6 (1041 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
S1PR3 Tclin Sphingosine 1-phosphate receptor Edg-3 (2543 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ALDH1A1 Tchem Aldehyde dehydrogenase 1A1 (77053 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
S1PR2 Tchem Sphingosine 1-phosphate receptor Edg-5 (1593 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
S1PR1 Tclin Sphingosine 1-phosphate receptor Edg-1 (5806 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CDK2 Tchem Cyclin-dependent kinase 2 (9050 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GLP1R Tclin Glucagon-like peptide 1 receptor (111429 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
S1PR5 Tclin Sphingosine 1-phosphate receptor Edg-8 (813 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
C5AR1 Tclin C5a anaphylatoxin chemotactic receptor (2677 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
AURKA Tchem Serine/threonine-protein kinase Aurora-A (10240 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
U2OS (164939 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CX3CR1 Tchem C-X3-C chemokine receptor 1 (1686 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
FPR2 Tchem Lipoxin A4 receptor (3472 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
FFAR4 Tchem G-protein coupled receptor 120 (2999 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
BRD4 Tchem Bromodomain-containing protein 4 (13122 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GPR35 Tchem G-protein coupled receptor 35 (2643 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TRIM24 Tchem Transcription intermediary factor 1-alpha (2087 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
BRPF1 Tchem Peregrin (2217 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
S1PR2 Tchem Sphingosine 1-phosphate receptor Edg-5/Sphingosine 1-phosphate receptor Edg-3 (2 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HEK-293T (167025 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADGRF1 Tbio Adhesion G-protein coupled receptor F1 (1591 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Aplnr Apelin receptor (201 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Mapk1 MAP kinase ERK2 (650 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Fgfr3 Fibroblast growth factor receptor 3 (21 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Gpr119 Glucose-dependent insulinotropic receptor (270 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Names and Identifiers

IUPAC Name [(E,2S,3R)-2-amino-3-hydroxyoctadec-4-enyl] dihydrogen phosphate
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

Certificates

Certificate of Analysis(COA)

Enter Lot Number to search for COA:

Find and download the COA for your product by matching the lot number on the packaging.

6 results found

Lot NumberCertificate TypeDateItem
K2229376Certificate of AnalysisNov 23, 2022 D130606
K2229502Certificate of AnalysisNov 23, 2022 D130606
H2205076Certificate of AnalysisJul 21, 2022 D130606
H2205077Certificate of AnalysisJul 21, 2022 D130606
C2228024Certificate of AnalysisMar 01, 2022 D130606
C2228035Certificate of AnalysisMar 01, 2022 D130606

Chemical and Physical Properties

SolubilitySoluble in warm acetic acid, 0.3M NaOH (~4 mg/ml), and methanol: THF: water (6:3:1) (>0.5 mg/ml). Insoluble in water.
SensitivityMoisture & Light & Air sensitive
Melt Point(°C)179-189°C

Safety and Hazards(GHS)

Pictogram(s) GHS07
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

Related Documents

Citations of This Product

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]

References

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]

Solution Calculators