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VPC 23019

Item № 13240
CAS № 449173-19-7
Purity ≥95%
product image
                (CAS 449173-19-7)
SIZE PRICE QUANTITY SUBTOTAL
CART TOTAL
     500 µg $29.00 0.00
     1 mg $52.00 0.00
     5 mg $189.00 0.00
     10 mg $261.00 0.00

Pricing updated 2019-07-18. Prices are subject to change without notice.

Description

Sphingosine-1-phosphate (S1P; Item No. 62570) is a bioactive lipid that exhibits a broad spectrum of biological activities including cell proliferation, survival, migration, cytoskeletal organization, and morphogenesis.1,2,3 It exerts its activity by binding to five distinct G protein-coupled receptors, S1P1/EDG-1, S1P2/EDG-5, S1P3/EDG-3, S1P4/EDG-6, and S1P5/EDG-8.1,2 VPC 23019 is an aryl amide-containing S1P analog that acts as a competitive antagonist at both S1P1 and S1P3 receptors (pKis = 7.86 and 5.93, respectively).4 It can inhibit S1P-induced migration of thyroid cancer cells, ovarian cancer cells, and neural stem cells.5

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Technical Information
Formal Name
(R)-2-amino-3-((3-octylphenyl)amino)-3-oxopropyl dihydrogen phosphate
CAS Number
449173-19-7
Molecular Formula
C17H29N2O5P
Formula Weight
372.4
Purity
≥95%
Formulation
A crystalline solid
λmax
245 nm
SMILES
O=C([C@H](N)COP(O)(O)=O)NC1=CC(CCCCCCCC)=CC=C1
InChI Code
InChI=1S/C17H29N2O5P/c1-2-3-4-5-6-7-9-14-10-8-11-15(12-14)19-17(20)16(18)13-24-25(21,22)23/h8,10-12,16H,2-7,9,13,18H2,1H3,(H,19,20)(H2,21,22,23)/t16-/m1/s1
InChI Key
MRUSUGVVWGNKFE-MRXNPFEDSA-N

Warning - this product is not for human or veterinary use.

Shipping & Storage
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Stability
≥ 2 years
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Additional Information

View the Cayman Structure Database for chemical structure definitions for many Cayman products

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References & Product Citations
Product Description References

1. Takuwa, Y., Takuwa, N., and Sugimoto, N. The Edg family G protein-coupled receptors for lysophospholipids: Their signaling properties and biological activities J. Biochem. 131(6), 767-771 (2002).

2. Ishii, I., Fukushima, N., Ye, X., et al. Lysophospholipid receptors: Signaling and biology Annu. Rev. Biochem. 73, 321-354 (2004).

3. Kluk, M.J., and Hla, T. Signaling of sphingosine-1-phosphate via the S1P/EDG-family of G-protein-coupled receptors Biochim. Biophys. Acta 1582(1-3), 72-80 (2002).

4. Davis, M.D., Clemens, J.J., Macdonald, T.L., et al. Sphingosine 1-phosphate analogs as receptor antagonists The Journal of Biological Chemisty 280(11), 9833-9841 (2005).

5. Takabe, K., Paugh, S.W., Milstien, S., et al. "Inside-out" signaling of sphingosine-1-phosphate: Therapeutic targets Pharmacological Reviews 60, 181-195 (2008).

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