An inhibitor of ecto-5’-nucleotidase
Technical Support & Resources

Information provided in the product description is from published literature. Due to the nature of scientific experimentation, your results (e.g., selectivity and effective concentrations) or specific application for this product may differ. If you have questions about how this product fits your application, please contact our technical support staff.

Visit our FAQ

Contact Us

Toll Free Phone (USA and Canada Only): (888) 526-5351
Direct Phone: (734) 975-3888

Request Technical Support

Technical Support Request

To streamline the process attach the appropriate questionnaire to your inquiry.

Download IHC QuestionnaireDownload WB Questionnaire

View Our Privacy Statement for details on how we use and protect your data. In addition, this site is protected by hCaptcha and its Privacy Policy and Terms of Service apply.

Guanosine 5'-methylenediphosphate (sodium salt)

Item No. 38378

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
guanosine, 5′-[hydrogen P-(phosphonomethyl)phosphonate], trisodium salt
Synonyms
  • Guanosine-5'-O-(α,β-methylene)diphosphate
  • GMP(CH2)P
  • GMP-CP
  • GpCH2p
Molecular Formula
C11H14N5O10P2 • 3Na
Formula Weight
507.2
Purity
≥95%
Formulation (Request formulation change)
A solution in water
Solubility(Learn about Variance in Solubility)
Water: Soluble
SMILES
O[C@@H]1[C@H](O)[C@@H](COP([O-])(CP([O-])([O-])=O)=O)O[C@H]1N2C=NC3=C2NC(N)=NC3=O.[Na+].[Na+].[Na+]
InChi Code
InChI=1S/C11H17N5O10P2.3Na/c12-11-14-8-5(9(19)15-11)13-2-16(8)10-7(18)6(17)4(26-10)1-25-28(23,24)3-27(20,21)22;;;/h2,4,6-7,10,17-18H,1,3H2,(H,23,24)(H2,20,21,22)(H3,12,14,15,19);;;/q;3*+1/p-3/t4-,6-,7-,10-;;;/m1.../s1
InChi Key
VAWFBFHLGPQUKF-MSQVLRTGSA-K
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Recommended Products

Certificates of Analysis & Batch Specific Data

Provide batch numbers separated by commas to download or request available product inserts, QC sheets, certificates of analysis, data packs, and GC-MS data.

Download most recent Certificate of Analysis for this product

    2.2 mg

    $224

    Add
    Product Description

    Guanosine 5'-methylenediphosphate is an inhibitor of ecto-5’-nucleotidase, also known as CD73 (Ki = 410 nM for the recombinant human enzyme).1 It also induces tubulin polymerization when used at a concentration of 1 mM.2 Guanosine 5'-methylenediphosphate has been used as a precursor in the synthesis of hydrolysis-resistant affinity resins for the purification of mRNA cap-binding proteins such as eukaryotic translation initiation factor 4E (eIF4E).3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Bhattarai, S., Pippel, J., Scaletti, E., et al. 2-substituted α,β-methylene-ADP derivatives: Potent competitive ecto-5'-nucleotidase (CD73) inhibitors with variable binding modes. J. Med. Chem. 63(6), 2941-2957 (2020).

    2. Sandoval, I.V., Jameson, J.L., Niedel, J., et al. Role of nucleotides in tubulin polymerization: Effect of guanosine 5'-methylene diphosphonate. Proc. Natl. Acad. Sci. USA 75(7), 3178-3182 (1978).

    3. Szczepaniak, S.A., Zuberek, J., Darzynkiewicz, E., et al. Affinity resins containing enzymatically resistant mRNA cap analogs--A new tool for the analysis of cap-binding proteins. RNA 18(7), 1421-1432 (2012).