D-erythro-sphingosine-1-phosphate - Moligand™, ≥98% , 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 S1, 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

CAS: 26993-30-6 Cat. No.: D130606 Molecular Weight: 379.472 EC Number: 636-659-1

GRADE & PURITY Moligand™, ≥98%

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

Storage

Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

Overview

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.

Specifications

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 & 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

Store at -20°C, Argon charged

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

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.

Purity

≥98%

Names and Identifiers

• Canonical Smiles: CCCCCCCCCCCCCC=CC(C(COP(=O)(O)O)N)O
• IUPAC Name: [(E,2S,3R)-2-amino-3-hydroxyoctadec-4-enyl] dihydrogen phosphate
• InChIKey: DUYSYHSSBDVJSM-KRWOKUGFSA-N
• 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
• Isomeric SMILES: CCCCCCCCCCCCC/C=C/[C@H]([C@H](COP(=O)(O)O)N)O
• WGK Germany: 3
• Molecular Weight: 379.472
• Reaxy-Rn: 29141682
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=29141682&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Sphingolipids
      • Subclass Phosphosphingolipids

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Sphingolipids
• Subclass: Phosphosphingolipids
• Intermediate Tree Nodes: Not available
• Direct Parent: Phosphosphingolipids
• Alternative Parents: Phosphoethanolamines Monoalkyl phosphates Secondary alcohols Organopnictogen compounds Organic oxides Monoalkylamines Hydrocarbon derivatives
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Sphingoid-1-phosphate or derivatives - Phosphoethanolamine - Monoalkyl phosphate - Organic phosphoric acid derivative - Phosphoric acid ester - Alkyl phosphate - Secondary alcohol - Amine - Organic oxygen compound - Primary amine - Organic nitrogen compound - Organooxygen compound - Organonitrogen compound - Alcohol - Primary aliphatic amine - Organopnictogen compound - Hydrocarbon derivative - Organic oxide - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as phosphosphingolipids. These are sphingolipids with a structure based on a sphingoid base that is attached to a phosphate head group. They differ from phosphonospingolipids which have a phosphonate head group.
• External Descriptors: Sphingoid base 1-phosphates

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

GPR12 Tbio G-protein coupled receptor 12 (0 Activities)

Discover Target: GPR12

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

GPR3 Tchem G-protein coupled receptor 3 (0 Activities)

Discover Target: GPR3

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

GPR63 Tchem Probable G-protein coupled receptor 63 (0 Activities)

Discover Target: GPR63

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

GPR6 Tchem G-protein coupled receptor 6 (0 Activities)

Discover Target: GPR6

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

S1PR5 Tclin Sphingosine 1-phosphate receptor 5 (12 Activities)

Discover Target: S1PR5

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

S1PR2 Tchem Sphingosine 1-phosphate receptor 2 (11 Activities)

Discover Target: S1PR2

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

S1PR4 Tclin Sphingosine 1-phosphate receptor 4 (9 Activities)

Discover Target: S1PR4

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

S1PR1 Tclin Sphingosine 1-phosphate receptor 1 (21 Activities)

Discover Target: S1PR1

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

S1PR3 Tclin Sphingosine 1-phosphate receptor 3 (19 Activities)

Discover Target: S1PR3

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

P2RY10 Tchem Putative P2Y purinoceptor 10 (1 Activities)

Discover Target: P2RY10

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

ABL1 Tclin Tyrosine-protein kinase ABL (18331 Activities)

Discover Target: ABL1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADRB2 Tclin Beta-2 adrenergic receptor (11824 Activities)

Discover Target: ADRB2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADRA2A Tclin Alpha-2a adrenergic receptor (9450 Activities)

Discover Target: ADRA2A

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

AGTR1 Tclin Type-1 angiotensin II receptor (5176 Activities)

Discover Target: AGTR1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

GSK3B Tclin Glycogen synthase kinase-3 beta (11785 Activities)

Discover Target: GSK3B

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CSNK1D Tchem Casein kinase I delta (4546 Activities)

Discover Target: CSNK1D

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

S1PR4 Tclin Sphingosine 1-phosphate receptor Edg-6 (1041 Activities)

Discover Target: S1PR4

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

S1PR3 Tclin Sphingosine 1-phosphate receptor Edg-3 (2543 Activities)

Discover Target: S1PR3

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ALDH1A1 Tchem Aldehyde dehydrogenase 1A1 (77053 Activities)

Discover Target: ALDH1A1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

S1PR2 Tchem Sphingosine 1-phosphate receptor Edg-5 (1593 Activities)

Discover Target: S1PR2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

S1PR1 Tclin Sphingosine 1-phosphate receptor Edg-1 (5806 Activities)

Discover Target: S1PR1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CDK2 Tchem Cyclin-dependent kinase 2 (9050 Activities)

Discover Target: CDK2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

GLP1R Tclin Glucagon-like peptide 1 receptor (111429 Activities)

Discover Target: GLP1R

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

S1PR5 Tclin Sphingosine 1-phosphate receptor Edg-8 (813 Activities)

Discover Target: S1PR5

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

C5AR1 Tclin C5a anaphylatoxin chemotactic receptor (2677 Activities)

Discover Target: C5AR1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

AURKA Tchem Serine/threonine-protein kinase Aurora-A (10240 Activities)

Discover Target: AURKA

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

U2OS (164939 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CX3CR1 Tchem C-X3-C chemokine receptor 1 (1686 Activities)

Discover Target: CX3CR1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

FPR2 Tchem Lipoxin A4 receptor (3472 Activities)

Discover Target: FPR2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

FFAR4 Tchem G-protein coupled receptor 120 (2999 Activities)

Discover Target: FFAR4

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

BRD4 Tchem Bromodomain-containing protein 4 (13122 Activities)

Discover Target: BRD4

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

GPR35 Tchem G-protein coupled receptor 35 (2643 Activities)

Discover Target: GPR35

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

TRIM24 Tchem Transcription intermediary factor 1-alpha (2087 Activities)

Discover Target: TRIM24

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

BRPF1 Tchem Peregrin (2217 Activities)

Discover Target: BRPF1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

S1PR2 Tchem Sphingosine 1-phosphate receptor Edg-5/Sphingosine 1-phosphate receptor Edg-3 (2 Activities)

Discover Target: S1PR2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HEK-293T (167025 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

Aplnr Apelin receptor (201 Activities)

Discover Target: Aplnr

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mapk1 MAP kinase ERK2 (650 Activities)

Discover Target: Mapk1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Fgfr3 Fibroblast growth factor receptor 3 (21 Activities)

Discover Target: Fgfr3

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Gpr119 Glucose-dependent insulinotropic receptor (270 Activities)

Discover Target: Gpr119

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• 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.
• Sensitivity: Moisture & Light & Air sensitive
• Melt Point(°C): 179-189°C
• Molecular Weight: 379.500 g/mol
• XLogP3: 1.900
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 17
• Exact Mass: 379.249 Da
• Monoisotopic Mass: 379.249 Da
• Topological Polar Surface Area: 113.000 Ų
• Heavy Atom Count: 25
• Formal Charge: 0
• Complexity: 372.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 2
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 1
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 1
• Covalently-Bonded Unit Count: 1

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,      [PMID:37245292] [10.1016/j.bbrc.2023.05.014]

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.  (2022)  Living symbiotic bacteria-involved skin dressing to combat indigenous pathogens for microbiome-based biotherapy toward atopic dermatitis.  Bioactive Materials,      [PMID:36157249] [10.1016/j.bioactmat.2022.08.019]

3. Qianyu Chen, Yayun Zhang, Langjie Ye, Shuai Gong, Hong Sun, Guanyong Su.  (2021)  Identifying active xenobiotics in humans by use of a suspect screening technique coupled with lipidomic analysis.  ENVIRONMENT INTERNATIONAL,      [PMID:34455192] [10.1016/j.envint.2021.106844]

4. Qianyu Chen, Yayun Zhang, Jianhua Li, Guanyong Su, Qi Chen, Zhen Ding, Hong Sun.  (2021)  Serum concentrations of neonicotinoids, and their associations with lipid molecules of the general residents in Wuxi City, Eastern China.  JOURNAL OF HAZARDOUS MATERIALS,      [PMID:33581671] [10.1016/j.jhazmat.2021.125235]

5. Li YAO, Yu-Xia YANG, Hui CAO, Huan-Huan REN, Zheng NIU, Ling SHI.  (2020)  Osthole attenuates pulmonary arterial hypertension by the regulation of sphingosine 1-phosphate in rats.  Chinese Journal of Natural Medicines,      [PMID:32402408] [10.1016/S1875-5364(20)30038-8]